Skip to main content
  • 279 Accesses

Abstract

Most biocatalysts can be used in a straightforward manner by regarding them as chiral catalysts and by applying standard methodology but, in addition, some special techniques have been developed in order to broaden their range of applications. In particular, using biocatalysts in nonaqueous media rather than in water can lead to the gain of some significant advantages as long as some specific guidelines are followed. Furthermore, ‘fixation’ of the enzyme by immobilization may be necessary, and the use of membrane technology may be advantageous as well. For both of the latter topics only the most simple techniques which can be adopted in an average organic chemistry laboratory are discussed (Chapter 3.2).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 74.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Borgström B, Brockman HL (eds.) (1984) Lipases. Elsevier, Amsterdam

    Google Scholar 

  2. Dordick JS (1989) Enzyme Microb. Technol. 11: 194

    Article  CAS  Google Scholar 

  3. Tramper J, Vermue MH, Beeftink HH, von Stockar U (1992) (eds) Biocatalysis in Non-Conventional Media. Elsevier, Amsterdam

    Google Scholar 

  4. Brink LES, Tramper J, Luyben KCAM, Vant’t Riet K (1988) Enzyme Microb. Technol. 10:736

    Article  CAS  Google Scholar 

  5. Klibanov AM (1990) Acc. Chem. Res. 23: 114

    Article  CAS  Google Scholar 

  6. Klibanov AM ( 1986) ChemTech 354

    Google Scholar 

  7. Klibanov AM (1989) Trends Biochem. Sci. 14: 141

    Article  CAS  Google Scholar 

  8. Laane C, Tramper J, Lilly MD (eds) (1987) Biocatalysis in Organic Media, Studies in Organic Chemistry, vol 29, Elsevier, Amsterdam

    Google Scholar 

  9. Gutman AL, Shapira M (1995) Adv. Biochem. Eng. Biotechnol. 52: 87

    CAS  Google Scholar 

  10. Koskinen AMP, Klibanov AM (eds) (1996) Enzymatic Reactions in Organic Media. Blackie Academic Professional, New York

    Google Scholar 

  11. Khmelnitsky YL, Levashov AV, Klyachko NL, Martinek K (1988) Enzyme Microb. Technol. 10:710

    Article  Google Scholar 

  12. Schultz GE, Schirmer RH (1979) Principles of Protein Structure. Springer, Berlin Heidelberg New York

    Book  Google Scholar 

  13. Bell G, Hailing PJ, Moore BD, Partidge J, Rees DG (1995) Trends Biotechnol. 13: 468

    Article  CAS  Google Scholar 

  14. Zaks A, Klibanov AM (1986) J. Am. Chem. Soc. 108: 2767

    Article  CAS  Google Scholar 

  15. Zaks A, Klibanov AM (1988) J. Biol. Chem. 263: 3194

    CAS  Google Scholar 

  16. Kazandjian RZ, Klibanov AM (1985) J. Am. Chem. Soc. 107: 5448

    Article  CAS  Google Scholar 

  17. Cooke R, Kuntz ID (1974) Ann. Rev. Biophys. Bioeng. 3: 95

    Article  CAS  Google Scholar 

  18. Bone S (1987) Biochim. Biophys. Acta 916: 128

    Article  CAS  Google Scholar 

  19. Rupley JA, Gratton E, Careri G (1983) Trends Biochem. Sci. 8: 18

    Article  CAS  Google Scholar 

  20. Cotterill IC, Sutherland AG, Roberts SM, Grobbauer R, Spreitz J, Faber K (1991) J. Chem. Soc., Perkin Trans. 1, 1365

    Google Scholar 

  21. Yamamoto Y, Yamamoto K, Nishioka T, Oda J (1989) Agric. Biol. Chem. 52: 3087

    Article  Google Scholar 

  22. Kazandjian RZ, Klibanov AM (1985) J. Am. Chem. Soc. 107: 5448

    Article  CAS  Google Scholar 

  23. Wang Y-F, Chen S-T, Liu K K-C, Wong C-H (1989) Tetrahedron Lett. 30: 1917

    Article  CAS  Google Scholar 

  24. Laumen K, Seemayer R, Schneider MP (1990) J. Chem. Soc., Chem. Commun. 49

    Google Scholar 

  25. Aldercreutz P, Mattiasson B (1987) Biocatalysis 1: 99

    Article  CAS  Google Scholar 

  26. Zaks A, Klibanov AM ( 1984) Science 224: 1249

    Article  CAS  Google Scholar 

  27. Rupley JA, Gratton E, Carieri G (1983) Trends Biochem. Sci. 8: 18

    Article  CAS  Google Scholar 

  28. Broos J, Visser AJWG, Engbersen JFJ, van Hoek A, Reinhoudt DN (1995) J. Am. Chem. Soc. 117: 12657

    Article  CAS  Google Scholar 

  29. Zaks A, Klibanov AM (1986) J. Am. Chem. Soc 108: 2767

    Article  CAS  Google Scholar 

  30. Russell AJ, Klibanov AM (1988) J. Biol. Chem. 263: 11624

    CAS  Google Scholar 

  31. Gaertner H, Puigserver A (1989) Eur. J, Biochem. 181:207

    Article  CAS  Google Scholar 

  32. Ferjancic A, Puigserver A, Gaertner A (1990) Appl. Microbiol. Biotechnol. 32: 651

    Article  CAS  Google Scholar 

  33. Tawaki S, Klibanov AM (1993) Biocatalysis 8: 3

    Article  CAS  Google Scholar 

  34. Ottolina G, Carrea G, Riva S (1991) Biocatalysis 5: 131

    Article  CAS  Google Scholar 

  35. Sakurai T, Margolin AL, Russell AJ, Klibanov AM (1988) J. Am. Chem. Soc. 110–7236

    Google Scholar 

  36. Kitaguchi H, Fitzpatrick PA, Huber JE, Klibanov AM (1989) J. Am. Chem. Soc. 111: 3094

    Article  CAS  Google Scholar 

  37. Fitzpatrick PA, Klibanov AM (1991) J. Am. Chem. Soc. 113:3166

    Article  CAS  Google Scholar 

  38. Kise H, Hayakawa A, Noritomi H (1990) J. Biotechnol. 14: 239

    Article  CAS  Google Scholar 

  39. Langrand G, Baratti J, Buono G, Triantaphylides C (1986) Tetrahedron Lett. 27: 29

    Article  CAS  Google Scholar 

  40. Koshiro S, Sonomoto K, Tanaka A, Fukui S (1985) J. Biotechnol. 2: 47

    Article  CAS  Google Scholar 

  41. Tnagaki T, Ueda H (1987) Agric. Biol. Chem. 51: 1345

    Article  Google Scholar 

  42. Morrow CJ, Wallace JS ( 1990) Synthesis of Polyesters by Lipase-Catalysed Polycondensalion in Organic Media. Abramowicz DA (ed) Biocatalysis, p 25, Van Nostrand Reinhold, New York

    Google Scholar 

  43. Margolin AL, Fitzpatrick PA, Klibanov AM (1991) J. Am. Chem. Soc. 113: 4693

    Article  CAS  Google Scholar 

  44. Gutman AL, Bravdo T (1989) J. Org. Chem. 54: 4263

    Article  CAS  Google Scholar 

  45. Makita A, Nihira T, Yamada Y (1987) Tetrahedron Lett. 28: 805

    Article  CAS  Google Scholar 

  46. Kitaguchi H, Fitzpatrick PA, Huber JE, Klibanov AM (1989) J. Am. Chem. Soc. 111: 3094

    Google Scholar 

  47. Gotor V, Brieva R, Rebolledo F (1988) Tetrahedron Lett. 29: 6973

    Article  CAS  Google Scholar 

  48. Kullmann W (1987) Enzymatic Peptide Synthesis; CRC Press, Boca Raton (FL)

    Google Scholar 

  49. Therisod M, Klibanov AM (1986) J. Am. Chem. Soc. 108: 5638

    Article  CAS  Google Scholar 

  50. Riva S, Klibanov AM (1988) J. Am. Chem. Soc. 110: 3291

    Article  CAS  Google Scholar 

  51. Riva S, Chopineau J, Kieboom APG, Klibanov AM (1988) J. Am. Chem. Soc. 110: 584

    Article  CAS  Google Scholar 

  52. Douzou P (1977) Cryobiochemistry; Academic Press, London

    Google Scholar 

  53. Fink AL, Cartwright SJ (1981) CRC Crit. Rev. Biochem. 11: 145

    Article  CAS  Google Scholar 

  54. Carrea G (1984) Trends Biotechnol. 2: 102

    Article  CAS  Google Scholar 

  55. Hailing PJ ( 1989) Trends Biotechnol. 7: 50

    Article  Google Scholar 

  56. Anderson E, Hahn-Hägerdal B (1990) Enzyme Microb. Technol. 12: 242

    Article  Google Scholar 

  57. Lilly MD (1982) J. Chem. Technol. Biotechnol. 32: 162

    Article  CAS  Google Scholar 

  58. Antonini E, Carrea G, Cremonesi P (1981) Enzyme Microb. Technol. 3: 291

    Article  CAS  Google Scholar 

  59. Kim KH, Kwon DY, Rhee JS (1984) Lipids 19: 975

    Article  CAS  Google Scholar 

  60. Brink LES, Tramper J (1985) Biotechnol. Bioeng. 27: 1258

    Article  CAS  Google Scholar 

  61. Furuhashi K (1992) Biological Routes to Optically Active Epoxides, In: Chirality in industry, Collins AN. Sheldrake GN, Crosby J (eds), p 167, Wiley: Chichester

    Google Scholar 

  62. Khrnelnitsky YL. Rich JO (1999) Curr. Opinion Chem. Biol. 3: 47

    Article  Google Scholar 

  63. Zaks A, Klibanov AM (1988) J. Biol. Chem. 263: 8017

    CAS  Google Scholar 

  64. Kastle JH, Loevenhart AS (1900) Am. Chem. J. 24: 491; see: ( 1901) J. Chem. Soc., Abstr. Sect. 80: 178

    Google Scholar 

  65. Klibanov AM (1997) Trends Biotechnol. 15: 97

    Article  CAS  Google Scholar 

  66. Faber K (1991) J. Mol. Catalysis 65: L49

    Article  CAS  Google Scholar 

  67. Johnson LN ( 1984) Inclusion Compds. 3: 509

    CAS  Google Scholar 

  68. Valivety RH, Brown L, Hailing PJ, Johnston GA, Suckling CJ (1990) Enzyme Reactions in Predominantly Organic Meida: Measurement and Changes of pH. In: Copping LG, Martin RE, Pickett JA, Bucke C, Bunch AW (eds) Opportunities in Biotransformations, p 81, Elsevier, London

    Google Scholar 

  69. Zaks A, Klibanov AM (1985) Proc. Natl. Acad. Sci. USA 82: 3192

    Article  CAS  Google Scholar 

  70. Hsu S-H, Wu S-S, Wang Y-F, Wong C-H (1990) Tetrahedron Lett. 31: 6403

    Article  CAS  Google Scholar 

  71. Clark DS (1994) Trends Biotechnol. 12: 439

    Article  CAS  Google Scholar 

  72. Laane C, Boeren S, Hilhorst R, Veeger C (1987) Optimization of Biocatalysts in Organic Media. Laane C, Tramper J, Lilly MD (eds) Biocatalysis in Organic Media, p 65, Elsevier, Amsterdam

    Google Scholar 

  73. Laane C, Boeren S, Vos K, Veeger C (1987) Biotechnol. Bioeng. 30: 81

    Article  CAS  Google Scholar 

  74. Rekker RF, de Kort HM (1979) Eur. J. Med., Chim. Ther. 14: 479

    CAS  Google Scholar 

  75. Bell G, Janssen AEM, Hailing PJ (1997) Enzyme Microb. Technol. 20: 471

    Article  CAS  Google Scholar 

  76. Hailing PJ (1994) Enzyme Microb. Technol. 16: 178

    Article  Google Scholar 

  77. Wehtje E, Costes D, Adlercreutz P (1997) J. Mol. Catal. B 3: 221

    Google Scholar 

  78. Hutcheon GA, Hailing PJ, Moore BD (1997) Methods Enzymol. 286 B: 465

    Article  Google Scholar 

  79. Kuhl P, Posselt S, Jakubke H-D (1981) Pharmazie 36: 436

    Google Scholar 

  80. Wehtje E, Kaur J, Adlercreutz P, Chand S, Mattiasson B (1997) Enzyme Microb. Technol. 21:502

    Article  CAS  Google Scholar 

  81. Robb DA, Yang Z, Hailing PJ (1994) Biocatalysis 9: 277

    Article  CAS  Google Scholar 

  82. Wehtje E, Svensson I, Adlercreutz P, Mattiasson B (1993) Biotechnol. Tech. 7: 873

    Article  CAS  Google Scholar 

  83. Tomazic SJ (1991) Protein Stabilization. In: Biocatalysts for Industry, Dordick JS (ed), p 241, Plenum Press: New York

    Google Scholar 

  84. Yamane T, Ichiryu T, Magata M, Ueno A, Shimizu S (1990) Biotechnol. Bioena. 36: 1063

    Article  CAS  Google Scholar 

  85. Freeman A (1984) Trends Biotechnol. 2: 147

    Article  CAS  Google Scholar 

  86. Mejri M, Pauthe E, Larreta-Garde V, Mathlouthi M (1998) Enzyme Microb. Technol. 23: 392

    Article  CAS  Google Scholar 

  87. Colaco CALS, Collett M, Roser BJ (1996) Chimica Oggi, July/August, 32

    Google Scholar 

  88. Yamamoyo Y, Kise H (1994) Bull. Chem. Soc. Jpn. 67: 1367

    Article  Google Scholar 

  89. Reslow M, Adlercreutz P, Mattiasson B (1992) Biocatalysis 6: 307

    Article  CAS  Google Scholar 

  90. Kitaguchi H, Klibanov AM (1989) J. Am. Chem. Soc. 111:9272

    Article  CAS  Google Scholar 

  91. Okamoto T, Ueji S (1999) Chem. Commun. 939

    Google Scholar 

  92. Ke T, Klibanov AM (1999) J. Am. Chem. Soc. 121: 3334

    Article  CAS  Google Scholar 

  93. Parker M-C, Brown SA, Robertson L, Turner NJ (1998) Chem. Commun. 2247

    Google Scholar 

  94. Tcrit 31 °C and pcrit 73 bar

    Google Scholar 

  95. Nakamura K (1990) Trends Biotechnol. 8: 288

    Article  CAS  Google Scholar 

  96. Mesiano AJ, Beckman EJ, Russell AJ (1999) Chem. Rev. 99: 623

    Article  CAS  Google Scholar 

  97. Russell A.I, Beckman EJ (1991) Appl. Biochem. Biotechnol. 31: 197

    Article  Google Scholar 

  98. Aaltonen O, Rantakylä M (1991) Chemtech 240

    Google Scholar 

  99. Marty A, Chulalaksananukul W, Condoret JS, Willemot RM, Durand G (1990) Biotechnol. Lett. 12: 11

    Article  CAS  Google Scholar 

  100. Chi YM, Nakamura K, Yano T (1988) Agric. Biol. Chem. 52: 1541

    Article  CAS  Google Scholar 

  101. Pasta P, Mazzola G, Carrea G, Riva S (1989) Biotechnol. Lett. 11: 643

    Article  CAS  Google Scholar 

  102. van Eijs AMM, de Jong PJP (1989) Procestechniek 8: 50

    Google Scholar 

  103. Randolph TW, Blanch HW, Prausnitz JM, Wilke CR (1985) Biotechnol. Lett. 7: 325

    Article  CAS  Google Scholar 

  104. Hammond DA, Karel M, Klibanov AM, Krukonis V (1985) J. Appl. Biochem. Biotechnol. 11: 393

    Article  CAS  Google Scholar 

  105. Randolph TW. Clark DS, Blanch HW, Prausnitz JM (1988) Science 238: 387

    Article  Google Scholar 

  106. Beckman EJ. Russell AJ (1993) J. Am. Chem. Soc. 115: 8845

    Article  Google Scholar 

  107. Kasche V, Schlothauer R, Brunner G (1988) Biotechnol. Lett. 10: 569

    Article  CAS  Google Scholar 

  108. Chulalaksananukul W, Condoret J-S, Combes D (1993) Enzyme Microb. Technol. 15: 691

    Article  CAS  Google Scholar 

  109. Loriner GH, Miziorko HM (1980) Biochemistry 19: 5321

    Article  Google Scholar 

  110. Ballesteros A, Bornscheuer U, Capewell A, Combes D, Condoret J-S, Koenig K, Kolisis FN, Marty A, Menge U, Scheper T, Stamatis H, Xenakis A (1995) Biocatalysis Biotrans. 13: 1

    Article  CAS  Google Scholar 

  111. Langrand G, Baratti J, Buono G, Triantaphylides C (1986) Tetrahedron Lett. 27: 29

    Article  CAS  Google Scholar 

  112. Koshiro S, Sonomoto K, Tanaka A, Fukui S (1985) J. Biotechnol. 2: 47

    Article  CAS  Google Scholar 

  113. Inagaki T, Ueda H (1987) Agric. Biol. Chem. 51: 1345

    Article  CAS  Google Scholar 

  114. Bornscheuer UT (1995) Enzyme Microb. Technol. 17: 578

    Article  CAS  Google Scholar 

  115. Björkling F, Godtfredsen SE, Kirk O (1989) J. Chem. Soc., Chem. Commun. 934

    Google Scholar 

  116. Bloomer S, Adlercreutz P, Mattiasson B (1992) Enzyme Microb. Technol. 14: 546

    Article  CAS  Google Scholar 

  117. Bell G, Blain JA, Paterson JDE, Shaw CEL, Todd RJ (1978) FEMS Microbiol. Lett. 3:223

    Article  CAS  Google Scholar 

  118. Paterson JDE, Blain JA, Shaw CEL, Todd RJ (1979) Biotechnol. Lett. 1:211

    Article  Google Scholar 

  119. Kvittingen L, Sjursnes B, Anthonsen T, Hailing P (1992) Tetrahedron 48: 2793

    Article  CAS  Google Scholar 

  120. Sarney DB, Vulfson EN (1995) Trends Biotechnol. 13: 164

    Article  CAS  Google Scholar 

  121. Björkling F, Godtfredsen SE, Kirk O (1989) J. Chem. Soc., Chem. Commun. 934

    Google Scholar 

  122. Riva S, Faber K (1992) Synthesis, 895

    Google Scholar 

  123. Santaniello E, Ferraboschi P, Grisenti P (1993) Enzyme Microb. Technol. 15: 367

    Article  CAS  Google Scholar 

  124. Andersch P, Berger M, Hermann J, Laumen K, Lobell M, Seemayer R. Waldingcr C. Schneider MP (1997) Methods Enzymol. 286 B: 406

    Article  Google Scholar 

  125. Kirchner G, Scollar MP, Klibanov AM (1985) J. Am. Chem. Soc. 107: 7072

    Article  CAS  Google Scholar 

  126. Mischitz M, Pöschl U, Faber K (1991) Biotechnol. Lett. 13: 653

    Article  CAS  Google Scholar 

  127. Ghogare A, Kumar GS (1989) J. Chem. Soc., Chem. Commun. 1533

    Google Scholar 

  128. Orrenius C, Öhrner N, Rotticci D, Mattson A, Hult K, Norin T (1995) Tetrahedron: Asymmetry 6: 1217

    Article  CAS  Google Scholar 

  129. Öhrner N, Martinelle M, Mattson A, Norin T, Hult K (1994) Biocatalysis 9: 105

    Article  Google Scholar 

  130. Degueil-Castaing M, De Jeso B, Drouillard S, Maillard B (1987) Tetrahedron Lett. 28:953

    Article  CAS  Google Scholar 

  131. Wang Y-F, Wong C-H (1988) J. Org. Chem. 53: 3127

    Article  CAS  Google Scholar 

  132. Wang Y-F, Lalonde JJ, Momongan M, Bergbreiter DE, Wong C-H (1988) J. Am. Chem. Soc. 110: 7200

    Article  CAS  Google Scholar 

  133. Donohue TM, Tuma DJ, Sorrell MF (1983) Arch. Biochem. Biophys. 220: 239

    Article  CAS  Google Scholar 

  134. Ledl F, Schleicher E (1990) Angew. Chem., Int. Ed. Engl. 29: 565

    Article  Google Scholar 

  135. Weber HK, Stecher H, Faber K (1995) Biotechnol. Lett. 17: 803

    Article  CAS  Google Scholar 

  136. Weber HK, Faber K (1997) Methods Enzymol. 286 B: 509

    Article  Google Scholar 

  137. Berger B, Faber K (1991) J. Chem. Soc., Chem. Commun. 1198

    Google Scholar 

  138. Sugai T, Ohta H (1989) Agric. Biol. Chem. 53: 2009

    Article  CAS  Google Scholar 

  139. Holla EW (1989) Angew. Chem., Int. Ed. Engl. 28: 220

    Article  Google Scholar 

  140. Kaga H, Siegmund B, Neufellner E. Faber K, Paltauf F (1994) Biotechnol. Tech. 8: 369

    Article  CAS  Google Scholar 

  141. Schudok M. Kretzschmar G (1997) Tetrahedron Lett. 38: 387

    Article  CAS  Google Scholar 

  142. Akai S, Naka T, Takebe Y, Kita Y (1997) Tetrahedron Lett. 38: 4243

    Article  CAS  Google Scholar 

  143. Kita Y, Takebe Y, Murata K, Naka T, Akai S (1996) Tetrahedron Lett. 37: 7369

    Article  CAS  Google Scholar 

  144. Bianchi D, Cesti P, Battistel E (1988) J. Org. Chem. 53: 5531

    Article  CAS  Google Scholar 

  145. Berger B, Rabiller CG, Königsberger K, Faber K, Griengl H (1990) Tetrahedron: Asymmetry 1: 541

    Article  CAS  Google Scholar 

  146. Guibe-Jampel E, Chalecki Z, Bassir M, Gelo-Pujic M (1996) Tetrahedron 52: 4397

    Article  CAS  Google Scholar 

  147. Keumi T, Hiraoka Y, Ban T, Takahashi I, Kitajima H (1991) Chem. Lett. 1989

    Google Scholar 

  148. Yamamoto K, Nishioka T. Oda J (1989) Tetrahedron Lett. 30: 1717

    Google Scholar 

  149. Nicotra F, Riva S, Secundo F. Zucchelli L (1990) Synth. Commun. 20: 679

    Article  CAS  Google Scholar 

  150. Suginaka K, Hayashi Y, Yamamoto Y (1996) Tetrahedron: Asymmetry 7: 1153

    Article  CAS  Google Scholar 

  151. Bevinakatti HS, Newadkar RV (1993) Tetrahedron: Asymmetry 4: 773

    Article  CAS  Google Scholar 

  152. Fourneron J-D, Chiche M, Pieroni G, (1990) Tetrahedron Lett. 31: 4875

    Article  CAS  Google Scholar 

  153. Caer E, Kindler A (1962) Biochemistry 1: 518

    Article  Google Scholar 

  154. Suemune H, Mizuhara Y, Akita H, Sakai K (1986) Chem. Pharm. Bull. 34: 3440

    Article  CAS  Google Scholar 

  155. Morishima H, Koike Y, Nakano M, Atsuumi S, Tanaka S, Funabashi H, Hashimoto J, Sawasaki Y, Mino N, Nakano K, Matsushima K, Nakamichi K, Yano M (1989) Biochem. Biophys. Res. Commun. 159: 999

    Article  CAS  Google Scholar 

  156. Santaniello E, Ferraboschi P, Grisenti P (1990) Tetrahedron Lett. 31: 5657

    Article  CAS  Google Scholar 

  157. Banfi L, Guanti G (1993) Synthesis 1029

    Google Scholar 

  158. Atsuumi S, Nakano M, Koike Y, Tanaka S, Ohkubo M (1990) Tetrahedron Lett. 31: 1601

    Article  Google Scholar 

  159. Baba N, Yoneda K, Tahara S, Iwase J, Kaneko T, Matsuo M (1990). 1. Chem. Soc. Chem. Commun. 1281

    Google Scholar 

  160. Terao Y, Murata M, Achiwa K (1988) Tetrahedron Lett. 29: 5173

    Article  CAS  Google Scholar 

  161. Ader U, Breitgoff D, Laumen KE, Schneider MP (1989)Tetrahedron Lett. 30: 1793

    Article  CAS  Google Scholar 

  162. Ferraboschi P, Grisenti P, Manzocchi A, Santaniello E (1990) J. Org. Chem. 55: 6214

    Article  CAS  Google Scholar 

  163. Laumen K, Breitgoff D, Schneider MP (1988) J. Chem. Soc., Chem. Commun. 1459

    Google Scholar 

  164. Anderson EM, Larson KM, Kirk O (1998) Biocatalysis Biotrans. 16: 181

    Article  CAS  Google Scholar 

  165. Finn MG, Sharpless KB (1985) Asymmetric Synthesis, Morrison JC (ed), vol 5, p 247, Academic Press, New York

    Google Scholar 

  166. Carlier PR. Mungali WS, Schroder G, Sharpless KB (1988) J. Am. Chem. Soc. 110: 2978

    Article  CAS  Google Scholar 

  167. Burgess K, Jennings LD (1990) J. Am. Chem. Soc. 112: 7434

    Article  CAS  Google Scholar 

  168. Burgess K, Jennings LD (1991) J. Am. Chem. Soc. 113: 6129

    Article  CAS  Google Scholar 

  169. Hayward RC, Overton CH, Witham GH (1976) J. Chem. Soc., Perkin Trans. 1, 2413

    Article  Google Scholar 

  170. Cunningham AF, Ktindig EP (1988) J. Org. Chem. 53: 1823

    Article  CAS  Google Scholar 

  171. Seemayer R, Schneider MP (1991) J. Chem. Soc., Chem. Commun. 49

    Google Scholar 

  172. Hemmerle H, Gais HJ (1987) Tetrahedron Lett. 28: 3471

    Article  CAS  Google Scholar 

  173. Xie ZF, Nakamura I, Suemune H, Sakai K (1988) J. Chem. Soc., Chem. Commun. 966

    Google Scholar 

  174. Laumen K, Seemayer R, Schneider MP (1990) J. Chem. Soc., Chem. Commun. 49

    Google Scholar 

  175. Chen C-S, Liu Y-C, Marcella M (1990) J. Chem. Soc., Perkin Trans 1, 2559

    Article  Google Scholar 

  176. Chen C-S, Liu Y-C (1989) Tetrahedron Lett. 30: 7165

    Article  CAS  Google Scholar 

  177. Hiratake J, Inagaki M, Nishioka T, Oda J (1988) J. Org. Chem. 53: 6130

    Article  CAS  Google Scholar 

  178. Solladié-Cavallo A (1989) In: Advances in Metal-Organic Chemistry; Liebeskind LS (ed), vol 1, JAI Press, p 99–131

    Google Scholar 

  179. Nakamura K, Ishihara K, Ohno A, Uemura M, Nishimura H, Hayashi Y (1990) Tetrahedron Lett. 31: 3603

    Article  CAS  Google Scholar 

  180. Yamazaki Y, Hosono K (1990) Tetrahedron Lett. 31: 3895

    Article  CAS  Google Scholar 

  181. Gokel GW, Marquarding D, Ugi IK (1972) J. Org. Chem. 37: 3052

    Article  CAS  Google Scholar 

  182. Boaz NW (1989) Tetrahedron Lett. 30: 2061

    Article  CAS  Google Scholar 

  183. Feichter C, Faber K, Griengl H (1989)Tetrahedron Lett. 30: 551

    Article  CAS  Google Scholar 

  184. Feichter C, Faber K, Griengl H (1990) Biocatalysis 3: 145

    Article  CAS  Google Scholar 

  185. Burgess K, Henderson I (1990) Tetrahedron: Asymmetry 1; 57

    Article  CAS  Google Scholar 

  186. Burgess K, Cassidy J, Henderson I (1991) J. Org. Chem. 56: 2050

    Article  CAS  Google Scholar 

  187. Burgess K, Jennings LD (1990) J. Org. Chem. 55: 1138

    Article  CAS  Google Scholar 

  188. Pfenninger A (1986) Synthesis 89

    Google Scholar 

  189. Babiak KA, Ng JS, Dygos JH. Weyker CL, Wang Y-F, Wong C-H (1990) J. Org. Chem. 55: 3377

    Article  CAS  Google Scholar 

  190. Baba N, Mimura M, Hiratake J, Uchida K, Oda J (1988) Agric. Biol. Chem. 52: 2685

    Article  CAS  Google Scholar 

  191. Baba N, Tateno K, Iwasa J, Oda J (1990) Agric. Biol. Chem. 54: 3349

    Article  CAS  Google Scholar 

  192. Thuring JWJF, Klunder AJH, Nefkens GHL, Wegman MA, Zwanenburg B (1996) Tetrahedron Lett. 37: 4759

    Article  CAS  Google Scholar 

  193. van den Heuvel M, Cuiper AD, van der Deen H, Kellogg RM, Feringa BL (1997) Tetrahedron Lett. 38: 1655

    Article  Google Scholar 

  194. van der Deen H, Cuiper AD, Hof RP, van Oeveren A, Feringa BL, Kellogg RM (1996) J. Am. Chem. Soc. 118: 3801

    Article  Google Scholar 

  195. Larsson ALE, Persson BA, Bäckvall J-E (1997) Angew. Chem., Int. Ed. Engl. 36: 1211

    Article  CAS  Google Scholar 

  196. Dinh PM, Howarth JA, Hudnott AR, Williams JMJ, Harris W (1996) Tetrahedron Lett. 37: 7623

    Article  CAS  Google Scholar 

  197. Mitsuda S, Nabeshima S, Hirohara H (1989) Appl. Microbiol. Biotechnol. 31: 334

    Article  CAS  Google Scholar 

  198. Tinapp P (1971) Chem. Ber. 104:2266

    Article  CAS  Google Scholar 

  199. Kruse CG (1992) Chiral Cyanohydrins. In: Chirality in Industry, Collins AN. Sheldrake GN, Crosby J (eds), p 279, Wiley: New York

    Google Scholar 

  200. Satoh T, Suzuki S, Suzuki Y, Miyaji Y, Imai Z (1969) Tetrahedron Lett. 10: 4555

    Article  Google Scholar 

  201. Mitsuda S, Yamamoto H, Umemura T, Hirohara H, Nabcshima S (1990) Agric. Biol. Chem. 54: 2907

    Article  CAS  Google Scholar 

  202. Effenberger F, Gutterer B, Ziegler T, Eckhardt E, Aichholz R (1991) Liebigs Ann. Chem. 47

    Google Scholar 

  203. Wang Y-F, Chen S-T, Liu K K-C, Wong C-H (1989) Tetrahedron Lett. 30: 1917

    Article  CAS  Google Scholar 

  204. Effenberger F, Ziegler T, Förster S (1987) Angew. Chem., Int. Ed. Engl. 26: 458

    Article  Google Scholar 

  205. Inagaki M, Hiratake J, Nishioka T, Oda J (1992) J. Org. Chem. 57: 5643

    Article  CAS  Google Scholar 

  206. Brand S, Jones MF, Rayner CM (1995) Tetrahedron Lett. 36: 8493

    Article  CAS  Google Scholar 

  207. Persson BA. Larsson ALE, Le Ray M, Backvall J-E (1999) J. Am. Chem. Soc. 121: 1645

    Article  CAS  Google Scholar 

  208. Greene TW (1981) Protective groups in Organic Chemistry, Wiley, New York

    Google Scholar 

  209. Bashir NB, Phythian SJ, Reason AJ, Roberts SM (1995) J. Chem. Soc., Perkin Trans. 1, 2203

    Article  Google Scholar 

  210. Hennen WJ, Sweers HM, Wang Y-F, Wong C-H (1988) J. Org. Chem. 53: 4939

    Article  CAS  Google Scholar 

  211. Therisod M, Klibanov AM (1986) J. Am. Chem. Soc. 108: 5638

    Article  CAS  Google Scholar 

  212. Riva S, Chopineau J, Kieboom APG, Klibanov AM (1988) J. Am. Chem. Soc. 110: 584

    Article  CAS  Google Scholar 

  213. Riva S, Klibanov AM (1988) J. Am. Chem. Soc. 110:3291

    Article  CAS  Google Scholar 

  214. Riva S, Bovara R, Ottolina G. Secundo F, Carrea G (1989) J. Org. Chem. 54: 3161

    Article  CAS  Google Scholar 

  215. Colombo D, Ronchetti F, Toma L (1991) Tetrahedron 47: 103

    Article  CAS  Google Scholar 

  216. Thcrisod M, Klibanov AM (1987) J. Am. Chem. Soc. 109: 3977

    Article  Google Scholar 

  217. Nicotra F, Riva S, Secundo F, Zucchelli L (1989) Tetrahedron Lett. 30: 1703

    Article  CAS  Google Scholar 

  218. Humicola lanuginosa was reclassified as Thermomyces lanuginosus.

    Google Scholar 

  219. Gruters RA. Neefjes JJ, Tersmette M, De Goede REJ, Tulp A, Huisman HG, Miedema F, Ploegh HL (1987) Nature 330: 74

    Article  CAS  Google Scholar 

  220. Margolin AL, Delinck DL, Whalon MR (1990) J. Am. Chem. Soc. 112: 2849

    Article  CAS  Google Scholar 

  221. Gatfield IL (1984) Ann. N. Y. Acad. Sci. 434: 569

    Article  CAS  Google Scholar 

  222. Gutman AL, Oren D, Boltanski A, Bravdo T (1987) Tetrahedron Lett. 28: 5367

    Article  CAS  Google Scholar 

  223. Guo Z, Ngooi TK, Scilimati A, Fülling G, Sih CJ (1988) Tetrahedron Lett. 29: 5583

    Article  CAS  Google Scholar 

  224. Gutman AL, Zuobi K, Boltansky A (1987) Tetrahedron Lett. 28: 3861

    Article  CAS  Google Scholar 

  225. Henkel B, Kunath A, Schick H (1993) Tetrahedron: Asymmetry 4: 153

    Article  CAS  Google Scholar 

  226. Gutman AL, Bravdo T (1989) J. Org. Chem. 54: 4263

    Article  CAS  Google Scholar 

  227. Makita A, Nihira T, Yamada Y (1987) Tetrahedron Lett. 28: 805

    Article  CAS  Google Scholar 

  228. Guo Z, Sih CJ (1988) J. Am. Chem. Soc. 110: 1999

    Article  CAS  Google Scholar 

  229. Ngooi TK, Scilimati A, Guo Z-W, Sih CJ (1989) J. Org. Chem. 54: 91 i

    Article  Google Scholar 

  230. Lobell M, Schneider MP (1993) Tetrahedron: Asymmetry 4: 1027

    Article  CAS  Google Scholar 

  231. Gotor V (1992) Enzymatic Aminolysis, Hydrazinolysis and Oximolysis Reactions. In: Servi S (ed) Microbial Reagents in Organic Synthesis, p 199, Kluwer: Dordrecht

    Google Scholar 

  232. Garcia MJ, Rebolledo F, Gotor V (1993) Tetrahedron Lett. 34: 6141

    Article  CAS  Google Scholar 

  233. Chen S-T. Jang M-K, Wang K-T (1993) Synthesis 858

    Google Scholar 

  234. Gotor V, Brieva R. Gonzalez C, Rebolledo F (1991) Tetrahedron 47: 9207

    Article  CAS  Google Scholar 

  235. Rebolledo F, Brieva R, Gotor V (1989) Tetrahedron Lett. 30: 5345

    Article  CAS  Google Scholar 

  236. Fastrez J, Fersht AR (1973) Biochemistry 12: 2025

    Article  CAS  Google Scholar 

  237. Yagisawa S (1981) J. Biochem. (Tokyo) 89: 491

    CAS  Google Scholar 

  238. Asterga C, Rebolledo F, Gotor V (1991) Synthesis 350

    Google Scholar 

  239. Gotor V, Brieva R, Gonzalez C, Rebolledo F (1991) Tetrahedron 47: 9207

    Article  CAS  Google Scholar 

  240. Gotor V, Brieva R, Rebolledo F (1988) Tetrahedron Lett. 29: 6973

    Article  CAS  Google Scholar 

  241. de Zoete MC, Kock-van Dalen AC, van Rantwijk F, Sheldon RA (1993) J. Chem. Soc., Chem. Commun. 1831

    Google Scholar 

  242. Gotor V, Brieva R, Rebolledo F (1988) J. Chem. Soc., Chem. Commun. 957

    Google Scholar 

  243. Balkenhohl F, Dietrich K, Hauer B, Ladner W (1997) J. Prakt. Chem. 339: 381

    Article  CAS  Google Scholar 

  244. Messina F, Botta M, Gorelli F, Schneider MP, Fazio F (1999) J. Org. Chem. 64: 3767

    Article  CAS  Google Scholar 

  245. Roche D, Prasad K, Repic O (1999) Tetrahedron Lett. 40: 3665

    Article  CAS  Google Scholar 

  246. Brieva R, Rebolledo F, Gotor V (1990) J. Chem, Soc., Chem. Commun. 1386

    Google Scholar 

  247. Takayama S, Lee ST, Chung S-C, Wong C-H (1999) Chem. Commun. 127

    Google Scholar 

  248. In principle, ethyl fluoroacetale would also fall into this category. However, its use is not recommended since fluoroacetic acid is a severe toxin by acting as inhibitor of the Krebs-cycle.

    Google Scholar 

  249. Ladner WE, Ditrich K (1999) Chimica Oggi, July/August. 51

    Google Scholar 

  250. Orsat B, Alper PB, Moree W, Mak C-P, Wong C-H (1996) J. Am. Chem. Soc. 118: 712

    Article  CAS  Google Scholar 

  251. Takayama S, Moree WJ, Wong C-H (1996) Tetrahedron Lett. 37: 6287

    Article  CAS  Google Scholar 

  252. Smidt H, Fischer A, Fischer P, Schmidt RD (1996) Biotechnol. Tech. 10: 335

    Article  CAS  Google Scholar 

  253. Reetz MT, Schimossek K (1996) Chimia 50: 668

    CAS  Google Scholar 

  254. Öhrner N, Orrenius C, Mattson A, Norin T. Hult K (1996) Enzyme Microb. Technol. 19: 328

    Article  Google Scholar 

  255. Baba N, Mirnura M, Oda J, Iwasa J (1990) Bull. Inst. Chem. Res. Kyoto Univ. 68: 208

    CAS  Google Scholar 

  256. Bianchi D, Cesti P (1990) J. Org. Chem. 55: 5657

    Article  CAS  Google Scholar 

  257. Kiefer M, Vogel R, Helmchen G, Nuber B (1994) Tetrahedron 50: 7109

    Article  CAS  Google Scholar 

  258. Fruton JS (1982) Adv. Enzymol. 53: 239

    CAS  Google Scholar 

  259. Jakubke H-D, Kuhl P, Könnecke A (1985) Angew. Chem., Int. Ed. Engl. 24: 85

    Article  Google Scholar 

  260. Jakubke H-D (1987) The Peptides 9: 103

    CAS  Google Scholar 

  261. Kullmann (1987) Enzymatic Peptide Synthesis, CRC Press, Boca Raton. FL

    Google Scholar 

  262. Morihara K (1987) Trends Biotechnol. 5: 164

    Article  CAS  Google Scholar 

  263. Glass JD (1981) Enzyme Microb. Technol. 3: 2

    Article  CAS  Google Scholar 

  264. Gill I. Lopez-Fandino R, Jorba X, Vulfson EN (1996) Enzyme Microb. Technol. 18: 162

    Article  CAS  Google Scholar 

  265. Chaiken IM, Komoriya A, Ojno M. Widmer F (1982) Appl. Biochem. Biotechnol. 7: 385

    Article  CAS  Google Scholar 

  266. Jakubke H-D (1995) Angew. Chem., Int. Ed. Engl. 34: 175

    Article  CAS  Google Scholar 

  267. Jackson DY, Burnier JP, Wells JA (1995) J. Am. Chem. Soc. 117:819

    Article  CAS  Google Scholar 

  268. Bergmann M, Fraenkel-Conrat H (1938) J. Biol. Chem. 124: 1

    CAS  Google Scholar 

  269. Kuhl P, Wilsdorf A, Jakubke H-D (1983) Monatsh. Chem. 114: 571

    Article  CAS  Google Scholar 

  270. Homandberg GA, Komoriya A, Chaiken IM (1982) Biochemistry 21: 3385

    Article  CAS  Google Scholar 

  271. Inouye K, Watanabe K, Tochino Y, Kobayashi M, Shigeta Y (1981) Biopolymers 20: 1845

    Article  CAS  Google Scholar 

  272. Gill I, Vulfson EN (1993) J. Am. Chem. Soc. 115: 3348

    Article  CAS  Google Scholar 

  273. Schellenberger V, Jakubke H-D (1991) Angew. Chem., Int. Ed. Engl. 30: 1437

    Article  Google Scholar 

  274. Margolin AL, Klibanov AM (1987) J. Am. Chem. Soc. 109: 3802

    Article  CAS  Google Scholar 

  275. West JB, Wong C-H (1987) Tetrahedron Lett. 28: 1629

    Article  CAS  Google Scholar 

  276. Matos JR. West JB, Wong C-H (1987) Biotechnol. Lett. 9: 233

    Article  CAS  Google Scholar 

  277. Crout DHG, MacManus DA, Ricca J-M, Singh S (1993) Indian J. Chem. 32B: 195

    CAS  Google Scholar 

  278. Gerisch S, Jakubke H-D, Kreuzfeld H-J (1995) Tetrahedron: Asymmetry 6: 3039

    Article  CAS  Google Scholar 

  279. Sekizaki H, Itoh K, Toyota E, Tanizawa K (1997) Tetrahedron Lett. 38: 1777

    Article  CAS  Google Scholar 

  280. Sekizaki H, Itoh K, Toyota E, Tanizawa K (1996) Chem. Pharm. Bull. 44: 1585

    Article  CAS  Google Scholar 

  281. Miyazawa T, Nakajo S, Nishikawa M, Imagawa K, Yanagihara R, Yamada T (1996) J. Chem. Soc. Perkin Trans. 1, 2867

    Article  Google Scholar 

  282. Gololobov MY, Petrauskas A, Pauliukonis R, Koske V, Borisov IL, Svedas V (1990) Biochim. Biophys. Acta 1041: 71

    Article  CAS  Google Scholar 

  283. Sekizaki H, Itoh K, Toyota E, Tanizawa K (1998) Chem. Pharm. Bull. 46: 846

    Article  CAS  Google Scholar 

  284. Isowa Y, Ohmori M, Ichikawa T, Mori K, Nonaka Y, Kihara K, Oyama K (1979) Tetrahedron Lett. 20:2611

    Article  Google Scholar 

  285. Stoineva IB, Petkov DD (1985) FEBS Lett. 183: 103

    Article  CAS  Google Scholar 

  286. Di Maio J, Nguyen TM-D, Lemieux C, Schiller PW (1982) J. Med. Chem. 25: 1432

    Article  Google Scholar 

  287. Inouye K, Watanabe K, Morihara K, Tochino K, Kanaya T, Emura J, Sakakibara S (1979) J. Am. Chem. Soc. 101:751

    Article  CAS  Google Scholar 

  288. Rose K, Gladstone J, Offord RE (1984) Biochem. I. 220: 189

    CAS  Google Scholar 

  289. Obermeier R, Seipke G (1984) In: Voelter W, Bayer E, Ovchinnikov YA, Wünsch E (eds) Chemistry of Peptides and proteins, vol 2, p 3, de Gruyter, Berlin

    Google Scholar 

  290. Masaki T, Nakamura K, Isono M, Soejima M (1978) Agric. Biol. Chem. 42: 1443

    Article  CAS  Google Scholar 

  291. Morihara K, Oka T, Tsuzuki H, Tochino Y, Kanaya T (1980) Biochem. Biophys. Res. Commun. 92: 396

    Article  CAS  Google Scholar 

  292. Hwang BK, Gu Q-M, Sih CJ (1993) J. Am. Chem. Soc. 115: 7912

    Article  CAS  Google Scholar 

  293. Björkling F, Frykman H, Godtfredsen SE, Kirk O (1992) Tetrahedron 48: 4587

    Article  Google Scholar 

  294. dc Zoete MC, van Rantwijk F, Maal L, Sheldon RA (1993) Recl. Trav. Chim. Pays-Bas 112:462

    Article  Google Scholar 

  295. Grunwald J, Wirz B, Scollar MP, Klibanov AM (1986) J. Am. Chem. Soc. 108: 6732

    Article  CAS  Google Scholar 

  296. Adlercreutz P (1996) Biocatalysis Biotrans. 14: 1

    Article  Google Scholar 

  297. Gorrebeeck C, Spanoghe M, Lanens D, Lemiere GL, Domisse RA, Lepoivre JA, Alderweireldt FC (1991) Recl. Trav. Chim. Pays-Bas 110: 231

    Article  CAS  Google Scholar 

  298. Snijder-Lambers AM, Vulfson EN, Doddema H Recl. Trav. Chim. Pays-Bas 110: 226

    Google Scholar 

  299. Adlercreutz P (1991) Eur. J. Biochem. 199: 609

    Article  CAS  Google Scholar 

  300. Itoh S, Terasaka T, Matsumiya M. Komatsu M, Ohshiro Y (1992) J. Chem. Soc. Perkin Trans. 1, 3253

    Article  Google Scholar 

  301. Duine JA. van der Meer RA, Groen BW (1990) Ann. Rev. Nutr. 10: 297

    Article  CAS  Google Scholar 

  302. Malmstrom BG, Ryden L (1968) In: Biological Oxidations; Singer TP (ed) p 419, Wiley. New York

    Google Scholar 

  303. Wood BJB. Ingranarti LL (1965) Nature 205: 291

    Article  CAS  Google Scholar 

  304. Kazandjian RZ. Klibanov AM (1985) 107: 5448

    Google Scholar 

  305. Siegel SM, Roberts K (1968) Space Life Sci. 1:131

    CAS  Google Scholar 

  306. Carrea G. Ottolina G, Riva S (1995) Trends Biotechnol. 13:63

    Article  CAS  Google Scholar 

  307. Margolin AL, Tai DF, Klibanov AM (1987) J. Am. Chem. Soc. 109: 7885

    Article  CAS  Google Scholar 

  308. Faber K, Ottolina G, Riva S (1993) Biocatalysis 8: 91

    Article  CAS  Google Scholar 

  309. Tawaki S, Klibanov AM (1992) J. Am. Chem. Soc. 114: 1882

    Article  CAS  Google Scholar 

  310. Wu S-H, Chu F-Y, Wang K-T (1991) Bioorg. Med. Chem. Lett. 1:339

    Article  CAS  Google Scholar 

  311. Ueji S, Fujino R, Okubo N, Miyazawa T, Kurita S, Kitadani M, Muromatsu A (1992) Biotechnol. Lett. 14: 163

    Article  CAS  Google Scholar 

  312. Kitaguchi H, Itoh I, Ono M (1990) Chem. Lett. 1203

    Google Scholar 

  313. Secundo F, Riva S, Carrea G (1992) Tetrahedron: Asymmetry 3: 267

    Article  CAS  Google Scholar 

  314. Suckling CJ, Suckling KE (1974) Chem. Soc. Rev. 3: 387

    Article  CAS  Google Scholar 

  315. Sharma BP, Bailey LF, Messing RA (1982) Angew. Chem., Int. Ed. Engl. 21, 837

    Article  Google Scholar 

  316. Tischer W. Wedekind F (1999) Top. Curr. Chem. 200: 95

    Article  CAS  Google Scholar 

  317. Rosevaer A (1984) J. Chem. Technol. Biotechnol. 34: 127

    Article  Google Scholar 

  318. Zaborsky OR (1973) Immobilized Enzymes, CRC Press, Cleveland, Ohio

    Google Scholar 

  319. Trevan MD (1980) Immobilized Enzymes: Introduction and Applications in Biotechnology, Wiley, New York

    Google Scholar 

  320. Hartmeier W (1986) Immobilisierte Biokatalysatoren. Springer, Berlin Heidelberg New York

    Google Scholar 

  321. Suckling CJ (1977) Chem. Soc. Rev. 6: 215

    Article  CAS  Google Scholar 

  322. Christen M, Crout DHG (1987) Enzymatic Reduction of β-Ketoestcrs using Immobilized Yeast. In: Bioreactors and Biotransformations, p 213, Moody GW, Baker PB (eds) Elsevier, London

    Google Scholar 

  323. Martinek K, Klibanov AM, Goldmacher VS, Tchernysheva AV, Mozhaev VV, Berezin IV, Glotov BO (1977) Biochim. Biophys. Acta 485: 13

    Article  CAS  Google Scholar 

  324. Klibanov AM (1983) Science 219: 722

    Article  CAS  Google Scholar 

  325. Miyawaki O, Wingard jr LB (1984) Biotechnol. Bioeng. 26: 1364

    Article  CAS  Google Scholar 

  326. Krakowiak W, Jach M, Korona J, Sugier H (1984) Starch 36: 396

    Article  CAS  Google Scholar 

  327. Bianchi D, Cesti P, Battistel E (1988) J. Org. Chem. 53: 5531

    Article  CAS  Google Scholar 

  328. Wiegel J, Dykstra M (1984) Appl. Microbiol. Biotechnol. 20: 59

    Article  CAS  Google Scholar 

  329. Kato T, Horikoshi K (1984) Biotechnol. Bioeng. 26: 595

    Article  CAS  Google Scholar 

  330. Sugiura M, Isobe M (1976) Chem. Pharm. Bull. 24: 72

    Article  CAS  Google Scholar 

  331. Hsu S-H, Wu S-S, Wang Y-F, Wong C-H (1990) Tetrahedron Lett. 31: 6403

    Article  CAS  Google Scholar 

  332. Akita H(1996)Biocatalysis 13: 141

    Google Scholar 

  333. Balcao VM, Paiva AL, Malcanta FX (1996) Enzyme Microb. Technol. 18: 392

    Article  CAS  Google Scholar 

  334. Lavayre J, Baratti J (1982) Biotechnol. Bioeng. 24: 1007

    Article  CAS  Google Scholar 

  335. Boudrant J, Ceheftel C (1975) Biotechnol. Bioeng. 17: 827

    Article  CAS  Google Scholar 

  336. Tosa T, Mori T, Fuse N, Chibata I (1967) Enzymologia 31: 214

    Google Scholar 

  337. Tosa T, Mori T, Chibata I (1969) Agric. Biol. Chem. 33: 1053

    Article  CAS  Google Scholar 

  338. Weetall HH, Mason RD (1973) Biotechnol. Bioeng. 15: 455

    Article  CAS  Google Scholar 

  339. Cannon JJ. Chen L-F, Flickinger MC, Tsao GT (1984) Biotechnol. Bioeng. 26: 167

    Article  CAS  Google Scholar 

  340. Ibrahim M, Hubert P, Dellacherie E, Magdalou J, Muller J, Siest G (1985) Enzyme Microb. Technol. 7: 66

    Article  CAS  Google Scholar 

  341. Monsan P, Combes D (1984) Biotechnol. Bioeng. 26: 347

    Article  CAS  Google Scholar 

  342. Chipley JR (1974) Microbios 10: 115

    CAS  Google Scholar 

  343. Marek M, Valentova O, Kas J (1984) Biotechnol. Bioeng. 26: 1223

    Article  CAS  Google Scholar 

  344. Vilanova E, Manjon A, Iborra JL (1984) Biotechnol. Bioeng. 26: 1306

    Article  CAS  Google Scholar 

  345. Miyama H, Kobayashi T, Nosaka Y (1984) Biotechnol. Bioeng. 26: 1390

    Article  CAS  Google Scholar 

  346. Burg K, Mauz S, Noetzel S, Sauber K (1988) Angew. Makromol. Chem. 157: 105

    Article  CAS  Google Scholar 

  347. Wong SS, Wong L-JC (1992) Enzyme Microb. Technol. 14: 866

    Article  CAS  Google Scholar 

  348. Khan SS, Siddiqui AM (1985) Biotechnol. Bioeng. 27: 415

    Article  CAS  Google Scholar 

  349. Kaul R, D’Souza SF. Nadkarni GB (1984) Biotechnol. Bioeng. 26: 901

    Article  CAS  Google Scholar 

  350. Quiocho FA, Richards FM (1964) Proc, Natl. Acad. Sci. USA 52: 833

    Article  CAS  Google Scholar 

  351. Persichetti RA, St. Clair NL, Griffith JP, Navia MA, Margolin AL (1995) J. Am. Chem. Soc. 117:2732

    Article  CAS  Google Scholar 

  352. Häring D, Schreier P (1999) Curr. Opinion Chem. Biol. 3: 35

    Article  Google Scholar 

  353. Zclinski T, Waldmann H (1997) Angew. Chem., Int. Ed. Engl. 36: 722

    Article  Google Scholar 

  354. Margolin AL (1996) Trends Biotechnol. 14: 223

    Article  CAS  Google Scholar 

  355. St. Clair NL, Navia MA (1992) J. Am. Chem. Soc. 114:7314

    Article  CAS  Google Scholar 

  356. Karube I, Kawarai M, Matsuoka H, Suzuki S (1985) Appl. Microbiol. Biotechnol. 21: 270

    Article  CAS  Google Scholar 

  357. Qureshi N, Tamhane DV (1985) Appl. Microbiol. Biotechnol. 21: 280

    Article  CAS  Google Scholar 

  358. Umemura I, Takamatsu S, Sato T, Tosa T, Chibata I (1984) Appl. Microbiol. Biotechnol. 20: 291

    Article  CAS  Google Scholar 

  359. Reetz MT ( 1997) Adv. Mater. 9: 943

    Article  CAS  Google Scholar 

  360. Fukui S, Tanaka A (1984) Adv. Biochem. Eng. Biotechnol. 29: 1

    CAS  Google Scholar 

  361. Mori T, Sato T, Tosa T, Chibata I (1972) Enzymologia 43: 213

    CAS  Google Scholar 

  362. Martinek K, Klibanov AM, Goldmacher VS, Berezin IV (1977) Biochim. Biophys. Acta 485: 1

    Article  CAS  Google Scholar 

  363. Hoar TP. Schulman JH (1943) Nature 152: 102

    Article  CAS  Google Scholar 

  364. Bonner FJ. Wolf R. Luisi PL (1980) Solid Phase Biochem. 5: 255

    Article  CAS  Google Scholar 

  365. Poon PH, Wells MA (1974) Biochemistry 13: 4928

    Article  CAS  Google Scholar 

  366. Wells MA (1974) Biochemistry 13: 4937

    Article  CAS  Google Scholar 

  367. Martinek K, Levashov AV, Klyachko NL, Khmelnitsky YL, Berezin IV (1986) Eur. J. Biochem. 155: 453

    Article  CAS  Google Scholar 

  368. Luisi PL (1985) Angew. Chem., Int. Ed. Engl. 24: 439

    Article  Google Scholar 

  369. Luisi PL, Laane C (1986) Trends Biotechnol. 4: 153

    Article  CAS  Google Scholar 

  370. Meier P. Luisi PL (1980) Solid Phase Biochem. 5: 269

    Article  CAS  Google Scholar 

  371. Okahata Y, Niikura K, Ijiro K (1995) J. Chem. Soc., Perkin Trans. 1, 919

    Article  Google Scholar 

  372. Barbaric S, Luisi PL (1981) J. Am. Chem. Soc. 103: 4239

    Article  CAS  Google Scholar 

  373. Grandi C, Smith RE, Luisi PL (1981) J. Biol. Chem. 256: 837

    CAS  Google Scholar 

  374. Martinek K, Semenov AN, Berezin IV (1981) Biochim. Biophys. Acta 658: 76

    Article  CAS  Google Scholar 

  375. Martinek K, Levashov AV, Khmelnitsky YL, Klyachko NL, Berezin IV (1982) Science 218: 889

    Article  CAS  Google Scholar 

  376. Hilhorst R. Spruijt R, Laane C, Veeger C (1984) Eur. J. Biochem. 144: 459

    Article  CAS  Google Scholar 

  377. Fiaschel E, Wandrey C, Kula M-R (1983) Adv. Biochem. Eng./Biotechnol. 26: 73

    Article  Google Scholar 

  378. Kragl U, Vasic-Racki D, Wandrey C (1993) Indian J. Chem. 32B: 103

    CAS  Google Scholar 

  379. Biselli M, Kragl U, Wandrey C (1995) Reaction Engineering for Enzyme-Catalyzed Biotransformations. Drauz K, Waldmann H (eds) In: Enzyme Catalysis in Organic Synthesis, p 89, Verlag Chemie, Weinheim

    Google Scholar 

  380. Bednarski MD, Chenault HK, Simon ES, Whitesides GM (1987) J. Am. Chem. Soc. 109: 1283

    Article  CAS  Google Scholar 

  381. Grimes MT, Drueckhammer DG (1993) J. Org. Chem. 58: 6148

    Article  CAS  Google Scholar 

  382. Thiem J, Stangier P (1990) Liebigs Ann. Chem. 1101

    Google Scholar 

  383. van Eikeren P, Brose DJ, Muchmore DC, West JB (1990) Ann. N. Y.Acad. Sci. 613: 796

    Article  Google Scholar 

  384. Bückmann AF, Carrea G (1989) Adv. Biochem. Eng. Biotechnol. 39: 97

    Google Scholar 

  385. Bückmann AF, Kula M-R, Wichmann R, Wandrey C (1981) J. Appl. Biochem. 3: 301

    Google Scholar 

  386. Vasic-Racki DJ, Jonas M, Wandrey C, Hummel W, Kula M-R (1989) Appl. Microbiol. Biotechnol. 31:215

    Article  CAS  Google Scholar 

  387. Wykes JR, Dunnill P, Lilly MD (1972) Biochim. Biophys. Acta 286: 260

    Article  CAS  Google Scholar 

  388. Malinauskas AA, Kulis JJ (1978) Appl. Biochem. Microbiol. 14: 706

    Google Scholar 

  389. Lundblad RL (1991) Chemical Reagents for Protein Modification, 2nd edn. CRC Press, London

    Google Scholar 

  390. Glazer AN (1976) The Proteins, Neurath H, Hill RL (eds) vol II, p I, Academic Press. London

    Google Scholar 

  391. Reetz MT, Jaeger K-E ( 1999) Top. Curr. Chem. 200: 31

    Article  CAS  Google Scholar 

  392. Reetz MT, Becker MH, Kühling KM, Holzwarth A (1998) Angew. Chem., Int. Ed. Engi. 37: 2647

    Article  CAS  Google Scholar 

  393. Arnold FH, Volkov AA (1999) Curr. Opinion Chem. Biol. 3: 54

    Article  CAS  Google Scholar 

  394. Arnold FH, Moore JC (1999) Optimizing Industrial Enzymes by Directed Evolution. In: New Enzymes for Organic Synthesis, Scheper T (ed) p 1, Springer, Berlin Heidelberg New York

    Google Scholar 

  395. Inada Y, Yoshimoto T, Matsushima A, Saito Y (1986) Trends Biotechnol, 4: 68

    Article  CAS  Google Scholar 

  396. Inada Y, Matsushima A, Hiroto M, Nishimura H, Kodera Y (1995) Adv. Biochem. Eng. Biotechnol. 52: 129

    CAS  Google Scholar 

  397. Inada Y, Furukawa M, Sasaki H, Kodera Y, Hiroto M, Nishimura H, Matsushima A (1995) Trends Biotechnol. 13: 86

    Article  CAS  Google Scholar 

  398. Kodera Y, Takahashi K, Nishimura H, Matsushima A, Saito Y, Inada Y (1986) Biotechnol. Lett. 8: 881

    Article  CAS  Google Scholar 

  399. Takahashi K. Ajima A, Yoshimoto T, Okada M, Matsushima A, Tamaura Y, Inada Y (1985) J. Org. Chem. 50:3414

    Article  CAS  Google Scholar 

  400. Takahashi K, Ajima A, Yoshimoto T, Inada Y (1984) Biochem. Biophys. Res, Commun. 125:761

    Article  CAS  Google Scholar 

  401. Uemura T, Fujimori M, Lee H-H, Ikeda S, Aso K (1990) Aeric. Biol. Chem. 54: 2277

    Article  CAS  Google Scholar 

  402. Ferjancic A, Puigserver A, Gaertner H (1988) Biotechnol. Lett. 10: 101

    Article  CAS  Google Scholar 

  403. Pasta P, Riva S, Carrea G (1988) FEBS Lett. 236: 329

    Article  CAS  Google Scholar 

  404. Yoshimoto T, Ritani A, Ohwada K, Takahashi K, Kodera Y, Matsushima A, Saito Y, Inada Y (1987) Biochem. Biophys. Res. Commun. 148: 876

    Article  CAS  Google Scholar 

  405. Bückmann AF, Morr M, Johansson G (1981) Makromol. Chem. 182: 1379

    Article  Google Scholar 

  406. Bremen U, Gais H-J (1996) Tetrahedron: Asymmetry 7: 3063

    Article  CAS  Google Scholar 

  407. Beecher JE, Andrews AT, Vulfson EN (1990) Enzyme Microb. Technol. 12. 955

    Article  CAS  Google Scholar 

  408. Takahashi K, Nishimura H, Yoshimoto T, Saito Y, Inada Y (1984) Biochem. Biophys. Res. Commun. 121: 261

    Article  CAS  Google Scholar 

  409. Yoshimoto T, Takahashi K, Nishimura H, Ajima A, Tamaura Y, Inada Y (1984) Biotechnol. Lett. 6: 337

    Article  CAS  Google Scholar 

  410. Yoshimoto T, Mihama T, Takahashi K, Saito Y, Tamaura Y, Inada Y (1987) Biochem. Biophys. Res. Commun. 145: 908

    Article  CAS  Google Scholar 

  411. Nishio T, Takahashi K, Yoshimoto T, Kodera Y, Saito Y, Inada Y (1987) Biotechnol. Lett. 9: 187

    Article  CAS  Google Scholar 

  412. Matsushima A, Kodera Y, Takahashi K, Saito Y, Inada Y (1986) Biotechnol. Lett. 8: 73

    Article  CAS  Google Scholar 

  413. Ajima A, Yoshimoto T, Takahashi K, Tamaura Y, Saito Y, Inada Y (1985) Biotechnol. Lett. 7: 303

    Article  CAS  Google Scholar 

  414. Lee H, Takahashi K, Kodera Y, Ohwada K, Tsuzuki T, Matsushima A, Inada Y (1988) Biotechnol. Lett. 10: 403

    Article  CAS  Google Scholar 

  415. Babonneau M-T, Jaquier R, Lazaro R, Viallefont P (1989) Tetrahedron Lett. 30: 2787

    Article  CAS  Google Scholar 

  416. Matsushima A, Okada M, Inada Y 81984) FEBS Lett. 178: 275

    Google Scholar 

  417. Heiss L, Gais H-J (1995) Tetrahedron Lett. 36: 3833

    Article  CAS  Google Scholar 

  418. Ruppert S, Gais H-J (1997) Tetrahedron: Asymmetry 8: 3657

    Article  Google Scholar 

  419. Cambou B, Klibanov AM (1984) J. Am. Chem. Soc. 106: 2687

    Article  CAS  Google Scholar 

  420. Kirchner G, Scollar MP, Klibanov AM (1985) J. Am. Chem. Soc. 107: 7072

    Article  CAS  Google Scholar 

  421. For instance, glutamic acid dioleyl ester ribitol amide, didodecyl N-D-glucono-L-glutamate or Brij35.

    Google Scholar 

  422. Khmelnitsky YL, Rich JO (1999) Curr. Opinion Chem. Biol. 3: 47

    Article  CAS  Google Scholar 

  423. Okahata Y, Mori T (1997) Trends Biotechnol. 15: 50

    Article  CAS  Google Scholar 

  424. Mori T, Kobayashi A, Okahata Y (1998) Chem. Lett. 921

    Google Scholar 

  425. Okahata Y, Niikura K, Ijiro K (1995) J. Chem. Soc., Perkin Trans. 1, 919

    Article  Google Scholar 

  426. Okahata Y, Mori T (1998) J. Mol. Calai. B 5: 119

    Google Scholar 

  427. Jene Q, Pearson JC, Lowe CR (1997) Enzyme Microb. Technol. 20: 69

    Article  CAS  Google Scholar 

  428. For a rare case of selectivity-enhancement see: Okahata Y, Fiatano A, Ujiro K ( 1995) Tetrahedron: Asymmetry 6: 1311

    Article  Google Scholar 

  429. Braco L, Dabulis K, Klibanov AM (1990) Proc. Natl. Acad. Sci. USA 87: 274

    Article  CAS  Google Scholar 

  430. Stahl M, Jeppsson-Wistrand U, Mansson M-O, Mosbach K (1991) J. Am. Chem. Soc. 113: 9366

    Article  Google Scholar 

  431. Rich JO, Dordick JS (1997) J. Am. Chem. Soc. 119: 3245

    Article  CAS  Google Scholar 

  432. Wulff G (1995) Angew. Chem., Int. Ed. Engl. 34: 1812

    Article  CAS  Google Scholar 

  433. Kaiser ET (1988) Angew. Chem., Int. Ed. Engl. 27: 902

    Article  Google Scholar 

  434. Nakatsuka T, Sasaki T, Kaiser ET (1987) J. Am. Chem. Soc. 109: 3808

    Article  CAS  Google Scholar 

  435. Polgár L, Bender MC (1966) J. Am, Chem. Soc. 88: 3153

    Article  Google Scholar 

  436. Neet KE, Koshland DE (1966) Proc. Natl. Acad. Sci. (USA) 56: 1606

    Article  CAS  Google Scholar 

  437. Hilvert D (1989) Design of Enzymatic Catalysts, In Biocatalysis in Agricultural Biotechnology, Whitaker JR, Sonnet PE (eds) ACS Symposium Scries 389, p 14, Am. Chem. Soc., Washington

    Google Scholar 

  438. Häring D, Herderich M, Schuler E, Withopf B, Schreier P (1997) Tetrahedron: Asymmetry 8: 853

    Article  Google Scholar 

  439. Kaiser ET, Lawrence DS (1984) Science 226: 505

    Article  CAS  Google Scholar 

  440. Levine HL, Kaiser ET (1980) J. Am. Chem. Soc. 102: 343

    Article  CAS  Google Scholar 

  441. Slama JT, Radziejewski C, Oruganti SR, Kaiser ET (1984) J. Am. Chem. Soc. 106: 6778

    Article  CAS  Google Scholar 

  442. Radziejewski C, Ballou DP, Kaiser ET (1985) J. Am, Chem. Soc 107: 3352

    Article  CAS  Google Scholar 

  443. Aitken DJ, Alijah R, Onyiriuka SO, Suckling CJ, Wood HCS, Zhu L (1993) J. Chem. Soc., Perkin Trans. 1, 597

    Article  Google Scholar 

  444. Hilvert D, Hatanaka Y, Kaiser ET (1988) J. Am. Chem. Soc. 110: 682

    Article  CAS  Google Scholar 

  445. van der Velde F, Könernann L, van Rantwijk F, Sheldon RA (1998) Chem. Commun. 1891

    Google Scholar 

  446. Mutter M (1985) Angew. Chem., Int. Ed. Engl. 24: 639

    Article  Google Scholar 

  447. Murakami Y, Kikuchi J, Hisaeda Y, Hayashida O (1996) Chem. Rev. 96: 721

    Article  CAS  Google Scholar 

  448. Kirby AJ (1996) Angew. Chem., Int. Ed. Engl. 35: 705

    Article  Google Scholar 

  449. Allen JV, Roberts SM, Williamson NM (1999) Adv. Biochem. Eng. Biotechnol. 63: 125

    CAS  Google Scholar 

  450. Chadwick DJ, Marsh J (1991) Catalytic Antibodies, Ciba Foundation Symposium, vol 159, Wiley: New York

    Book  Google Scholar 

  451. Schultz PG (1989) Angew. Chem., Int. Ed. Engl. 28: 1283

    Article  Google Scholar 

  452. Kirby AJ ( 1996) Acta Chem. Scand. 50: 203

    Article  CAS  Google Scholar 

  453. Reymond J-L (1999) Top. Curr. Chem. 200: 59

    Article  CAS  Google Scholar 

  454. Lerner RA (1990) Chemtracts-Org. Chem. 3: 1

    CAS  Google Scholar 

  455. French DL, Laskov R, Scharff MD (1989) Science 244: 1152

    Article  CAS  Google Scholar 

  456. Pollack SJ, Schultz PG (1989) J. Am. Chem. Soc. 111: 1929

    Article  CAS  Google Scholar 

  457. Janjic N, Tramontano A (1989) J. Am. Chem. Soc. 111: 9109

    Article  CAS  Google Scholar 

  458. Janda KD, Ashley JA, Jones TM, McLeod DA, Schloeder DM, Weinhouse Ml (1990) J. Am. Chem. Soc. 112: 8886

    Article  CAS  Google Scholar 

  459. Janda KD, Schloeder D, Benkovic SJ. Lerner RA (1988) Science 241: 1188

    Article  CAS  Google Scholar 

  460. Tramontano A, Janda KD, Lerner RA (1986) Science 234: 1566

    Article  CAS  Google Scholar 

  461. Pollack SJ, Jacobs JW, Schultz PG (1986) Science 234: 1570

    Article  CAS  Google Scholar 

  462. Janda KD et al. (1991) J. Am. Chem. Soc. 113:291

    Article  CAS  Google Scholar 

  463. Napper AD, Benkovic SJ, Tramontano A. Lerner RA (1987) Science 237: 1041

    Article  CAS  Google Scholar 

  464. Janda KD, Benkovic S J, Lerner RA ( 1989) Science 244: 437

    Article  CAS  Google Scholar 

  465. Shokal KM, Leumann CJ, Sugasawara R, Schultz PG (1989) Nature 338: 269

    Article  Google Scholar 

  466. Uno T, Schultz PG (1992) J. Am. Chem. Soc. 114: 6573

    Article  CAS  Google Scholar 

  467. Nakayama GR. Schultz PG (1992) J. Am. Chem. Soc. 114: 780

    Article  CAS  Google Scholar 

  468. Hilvert D (1992) Pure Appl. Chem. 64: 1103

    Article  CAS  Google Scholar 

  469. Hoffmann T, Zhong G, List B. Shabat D, Anderson J, Gramatikova S. Lerner RA. Barbas III CF (1998) J. Am. Chem. Soc. 120: 2768

    Article  CAS  Google Scholar 

  470. Cochran AG, Sugasawara R, Schultz PG (1988) J. Am. Chem. Soc. 110: 7888

    Article  CAS  Google Scholar 

  471. Iverson BL, Cameron KE, Jahangiri GK, Pasternak DS (1990) J. Am. Chem. Soc. 112:5320

    Article  CAS  Google Scholar 

  472. Jackson DY, Schultz PG(1991) J. Am. Chem. Soc. 113:2319

    Article  CAS  Google Scholar 

  473. Hilvert D, Nared KD (1988) J. Am. Chem. Soc. 110: 5593

    Article  CAS  Google Scholar 

  474. Jackson DY. Jackson DY, Jacobs JW, Sugasawara R, Reich SH. Bartlett PA, Schultz PG (1988) J. Am. Chem. Soc. 110: 4841

    Article  CAS  Google Scholar 

  475. Braisted AC, Schultz PG (1990) J. Am. Chem. Soc. 112: 7430

    Article  CAS  Google Scholar 

  476. Meckel AAP, Resmini M, Pandit UK (1996) Bioorg. Med. Chem. 4: 1051

    Article  Google Scholar 

  477. Hasserodt J, Janda KD, Lerner RA (1997) J. Am. Chem. Soc. 119: 5993

    Article  CAS  Google Scholar 

  478. Hasserodt J, Janda KD, Lerner RA (1996) J. Am. Chem. Soc. 118: 11654

    Article  CAS  Google Scholar 

  479. Zhong G. Hoffmann T, Lerner RA. Danishefsky S, Barbas CF (1997) J. Am. Chem. Soc. 119: 8131

    Article  CAS  Google Scholar 

  480. Tramontano A, Ammanii AA, Lerner RA (1988) J. Am. Chem. Soc. 110: 2282

    Article  CAS  Google Scholar 

  481. Kitazume T, Lin JT, TakedaM. Yamazaki T (1991) J. Am. Chem. Soc. 113: 2123

    Article  CAS  Google Scholar 

  482. Sinha SC, Keinan E, Reymond J-L (1993) J. Am. Chem. Soc. 115: 4893

    Article  CAS  Google Scholar 

  483. Sinha SC, Keinan E (1995) J. Am. Chem. Soc. 117: 3653

    Article  CAS  Google Scholar 

  484. Janda KD, Shevlin CG, Lerner RA (1993) Science 259: 490

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 2004 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Faber, K. (2004). Special Techniques. In: Biotransformations in Organic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-18537-3_3

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-18537-3_3

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-20097-0

  • Online ISBN: 978-3-642-18537-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics