Abstract
Comparison of the list of branched-chain monosaccharides presented in the first review on this matter by Shafizadeh in 1956 with that given in this chapter and a recent chapter by Grisebach (1980) shows that not only new representatives of this class of natural compounds have been detected, but also that some (cordyceptose, abequose, tyvelose) had to be cancelled as a consequence of more detailed chemical analysis. Nevertheless, at present, some 20 monosaccharides with a branched skeleton are known, two of which are produced by green plants while the remaining originate from microorganisms.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Achenbach H, Grisebach H (1964) Biogenesis of the macrolides. XI. Biosynthesis of magnamycin. Z Naturforsch 19b: 561–568
Achenbach H, Karl W (1975a) Zur Struktur des Antibiotikums Aldgamycin E. Chem Ber 108: 759–771
Achenbach H, Karl W (1975b) Aldgamycin F, ein neues Antibiotikum aus Streptomyces lavendulae. Chem Ber 108: 780–789
Anderson RL, Hanson RE, Sapico VL (1975) D-Fructose-1-phosphate kinase. Methods Enzymol 42 C: 63–66
Ankel H, Feingold DS (1965) Biosynthesis of uridine diphosphate D-xylose. I. Uridine diphosphate glucuronate carboxy-lyase of wheat germ. Biochemistry 4: 2468–2475
Bacon JSD (1963) The occurrence of apiose in polysaccharide fractions from certain plants. Biochem J 89:103 P–104 P
Bacon JSD, Cheshire MV (1971) Apiose and mono-O-methyl sugars as minor constituents of the leaves of deciduous trees and various other species. Biochem J 124: 555–562
Baddiley J, Blumson NL, Di Girolamo A, Di Girolamo M (1961) Thymidine diphospate sugar derivatives and their transformation in Streptomyces griseus. Biochim Biophys Acta 50: 391–393
Bakhaeva GP, Berlin YA, Chuprunova OA, Kolosov MN, Peck GY, Piotrovich LA, Shemyakin MM, Vasina IV (1967) The stereochemistry of olivomycins. Chem Commun 1: 10–11
Bakhaeva GP, Berlin YA, Boldyreva EF, Chuprunova OA, Kolosov MN, Soifer VS, Vasiljeva TE, Yartseva IV (1968) The structure of aureolic acid (mithramycin). Tetrahedron Lett 32: 3595–3598
Baron D, Grisebach H (1973) Further studies on the mechanism of action of UDP-apiose/UDP-xylose synthase from cell cultures of parsley. Eur J Biochem 38: 153–159
Baron D, Streitberger U, Grisebach H (1973) Improved method for purification of UDP- apiose/UDP-xylose synthase from cell cultures of parsley. Biochim Biophys Acta 293: 526–533
Beck E (1967) Isolierung und Charakterisierung eines Apiogalakturonans aus der Zellwand von Lemna minor. Z Pflanzenphysiol 57: 444–461
Beck E (1969) Isolierung und Identifizierung von Clusianose, einem 1-O-oc-D-Galactopyrano-syl-Hamamelit. Z Pflanzenphysiol 61: 360–366
Beck E, Kandier O (1965) Apiose als Bestandteil der Zellwand höherer Pflanzen. Z Naturforsch 20 b: 62–67
Beck E, Kandier O (1966) Isotopenstudien zur Biosynthese von Apiose in Lemna. Z Pflanzenphysiol 55: 71–84
Beck E, Knaupp I (1974) Biosynthese der Hamamelose. III. Identifizierung von Hamamelose- 21,5-Diphosphat, Hamamelose-5-Phosphat und Hamamelose-21-Phosphat. Z Pflanzenphysiol 72: 141–147
Beck E, Sellmair J, Kandier O (1968) Biosynthese der Hamamelose. I. Die intramolekulare 14C-Verteilung in Hamamelose nach Assimilation von 14C02 und 14C-positionsmarkier- ter Glucose durch Blätter von Primula clusiana Tausch. Z Pflanzenphysiol 58: 434–451
Beck E, Stransky H, Fürbringer M (1971) Synthesis of hamamelose-diphosphate by isolated spinach chloroplasts. FEBS Lett 13: 229–234
Beck E, Wieczorek J, Reinecke W (1980) Purification and properties of hamamelosekinase. Eur J Biochem 107: 485–489
Bell DJ, Isherwood FA, Hardwick NE, Cahn RS (1954) D-(+)-Apiose from the monocotyledon, Posidonia australis. J Chem Soc: 3702–3706
Berlin YA, Esipov SE, Kolosov MN, Shemyahin MM (1966a) Olivomycin IV. The structure of olivomycin. Tetrahedron Lett 14: 1431–1436
Berlin YA, Esipov SE, Kolosov MN, Shemyakin MM (1966b) The structure of the olivomycin-chromomycin antibiotics. Tetrahedron Lett 15: 1643–1647
Beusekom CF van (1967) Über einige Apiose-Vorkommnisse bei den Helobiae. Phytochemistry 6: 573–576
Birch AJ, Cameron DW, Holloway RW, Rickards RW (1960) Further examples of biological C-methylation. Novobiocin and actinomycin. Tetrahedron Lett 25: 26–31
Birch A J, Holloway PW, Rickards RW (1962) Biosynthesis of noviose, a branched-chain monosaccharide. Biochim Biophys Acta 57: 143–145
Blumson NL, Baddiley J (1961) Thymidine diphosphate mannose and thymidine diphosphate rhamnose in streptomyces griseus. Biochem J 81: 114–124
Brimacombe JS, Smith CW, Minshall J (1974) A synthesis of methyl D-aldgaroside B. Tetrahedron Lett 35: 2997–3000
Brimacombe JS, Mahmood S, Rollins A J (1975) Branched-chain sugars V. Identification and synthesis of vinelose. J Chem Soc Perkin Trans 1: 1292–1297
Bruton J, Horner WH (1966) Biosynthesis of streptomycin III. Origin of the carbon atoms of streptose. J Biol Chem 241: 3142–3146
Burton JS, Overend WG, Williams NR (1965) Branched-chain sugars III. The introduction of branching into methyl 3,4-O-isopropylidene-ß-L-arabinoside and the synthesis of L- hamamelose. J Chem Soc: 3433–3445
Candy DJ, Baddiley J (1965) The biosynthesis of streptomycin: the origin of the C-formyl group of streptose. Biochem J 96: 526–529
Candy DJ, Blumson NL, Baddiley J (1964) Biosynthesis of streptomycin. Incorporation of 14C-labeled compounds into streptose and N-methyl-L-glucosamine. Biochem J 91:31–35 Chakraborti SR ( 1959 ) Chemical investigation of Indian species. Chem Abstr 22602a
Chakraborti SR (1959) Chemical investigation of Indian species. Chem Abstr 22602a
Chrastil J (1956) Identification of carbohydrates in kok-saghyz (Taraxacum kok-saghyz) and chromatography of apiose. Chem Listy 50: 163–164
Cooper DJ, Yudis MD, Guthrie RD, Prior AM (1971) The gentamicin antibiotics. I. Structure and absolute stereochemistry of methyl garosaminide. J Chem Soc (C): 960–963
Corcoran JW (1961) Actinomycete antibiotics II. Participation of the methionine methyl group in the biogenesis of L-cladinose, a branched-chain monosaccharide. J Biol Chem 236: PC 27–28
Corcoran JW (1964) The biosynthesis of erythromycin. Lloydia 27:1-14 Corcoran JW (1975) S-adenosylmethionine: erythromycin-C,0-methyltransferase. Methods Enzymol 43: 487–498
Corcoran JW (1975) S-adenosylmethionine: erythromycin-C,0-methyltransferase. Methods Enzymol 43:487–498
Darvill AG, McNeil M, Albersheim P (1978) Structure of plant cell walls VIII. A new pectic polysaccharide. Plant Physiol 62: 418–422
Davenport HE, Dupont MS (1972) The enzymic hydrolysis of malonated flavone glycosides. Biochem J 129:18 P–19 P
Duff RB (1965) The occurrence of apiose in Lemna (duckweed) and other angiosperms. Biochem J 94: 768–772
Duff RB, Knight AH (1963) The occurrence of apiose in Lemna (duckweed) and other angiosperms. Biochem J 88:33 P–34 P
Eguchi Y, Takagi M, Uda F, Kimata K, Okuda S, Suzuki N, Suzuki S (1973) Biosynthesis of branched-chain deoxysugars V. J Biol Chem 248: 3341–3352
Eickenbusch JD, Sellmair J, Beck E (1971) Biosynthese der Hamamelose II. Der Einbau von Radiokohlenstoff aus 14C-markierten Substanzen des Glykolat- und Tricarbonsäure-zyklus in Hamamelose in Blättern von Primula clusiana Tausch. Z Pflanzenphysiol 65: 24–34
Ellestad GA, Kunstmann MP, Lancaster JE, Mitscher LA, Morton G (1967) Structures of methyl aldgarosides A and B obtained from the neutral macrolide antibiotic aldgamycin E. Tetrahedron 23: 3893–3902
Ezekiel AD, Overend WG, Williams NR (1969) Branched-chain sugars IX. The synthesis of hamamelitannin. Carbohydr Res 11: 233–239
Farooq MO, Gupta SR, Riamuddin M, Rahman W, Seshadri TR (1953) Chemical examination of celery seeds. J Sci Ind Res 12 B: 400–407
Farooq MO, Varshney JP, Rahman W (1957) On the glycosides of Apium petroselinum (parsley). Naturwissenschaften 44: 444
Farooq MO, Varshney JP, Rahman W (1958) On the presence of apiin in Indian celery seeds C. (Apium graveolens). Naturwissenschaften 45: 265
Freudenberg K, Blümmel F (1924) Tannins and related compounds XVII. Hamameli-tannin III. Ann Chem 440: 45–59
Funabashi M, Yamazaki S, Yoshimura J (1975) Branched-chain sugars VII. Determination of the configuration of L-vinelose by synthesis. Carbohydr Res 44: 275–283
Ganguly AK, Sarre OZ (1969) Structure and absolute stereochemistry of evermicose. Chem Commun 1149–1150
Ganguly AK, Sarre OZ, Reimann H (1968) Evernitrose, a naturally occurring nitro sugar from everninomicins. J Am Chem Soc 90: 7129–7130
Ganguly AK, Sarre OZ, Szmulewicz S (1971) Structure of evertetrose and everninonitrose. Chem Commun 746
Gaugler RW, Gabriel O (1973) Biological mechanisms involved in the formation of deoxy sugars VII. J Biol Chem 248: 6041–6049
Gebb C, Baron D, Grisebach H (1975) Spectroscopic evidence for the formation of a 4-keto intermediate in the UDP-Apiose/UDP-Xylose synthase reaction. Eur J Biochem 54: 493–498
Gilck H (1972) Der Mechanismus der Hamamelose-Biosynthese: In vivo Untersuchungen mit Blättern von Primula clusiana Tausch. Thesis Univ Munich
Gilck H, Beck E (1974) Biosynthese der Hamamelose IV. Nachweis der Biosynthesesequenz: Fructose-diphosphat → Hamamelose-diphosphat → Hamamelose-monophosphat → Hamamelose. Z Pflanzenphysiol 72: 395–409
Gilck H, Thanbichler A, Sellmair J, Beck E (1975) A simple method for the isolation of crystalline D-hamamelose. Carbohydr Res 39: 160–161
Gonzales-Porque P, Strominger JL (1972) Enzymatic synthesis of cytidine diphosphate 3,6-dideoxyhexose VI. J Biol Chem 247: 6748–6756
Gottlieb D, Shaw PD (1967) Antibiotics. Springer, Berlin Heidelberg New York Grisebach H (1978) Biosynthesis of sugar components of antibiotic substances. Adv Carbohydr Chem 35: 81–126
Grisebach H (1978) Biosynthesis of sugar components of antibiotic substances. Adv Carbohydr Chem 35:81–126
Grisebach H (1980) Branched chain sugars: occurrence and biosynthesis. In: Stumpf PK, Conn EE (eds) The biochemistry of plants, Vol. Ill Preiss J (ed) Carbohydrates: structure and function. Academic Press, New York
Grisebach H, Achenbach H (1962) Biogenesis of the macrolides V. The origin of the carbon chain of mycarose. Z Naturforsch 17 b: 63–64
Grisebach H, Bilhuber W (1967) Zur Biosynthese des Apigenins und Chrysoeriols in der Petersilie. Z Naturforsch 22 b: 746–751
Grisebach H, Döbereiner U (1966) Zur Biosynthese der Apiose I. Einbau markierter Vorstufen in Apiose bei Apium petroselinum. Z Naturforsch 21 b: 429–435
Grisebach H, Sandermann H Jr (1966) Zur Biosynthese der Apiose II. D-Glucuronsäureals spezifische Vorstufe der D-Apiose in Petersilie. Biochem Z 346: 322–327
Grisebach H, Schmid R (1972) Chemie und Biochemie verzweigtkettiger Zucker. Angew Chem 84: 192–206
Gustine DL, Yuan DHF, Kindel PK (1975) Uridine diphosphate D-glucuronic acid cyclase and uridine diphosphate D-glucuronic acid carboxy-lyase I from Lemna minor. Purification, characterization, and separation from uridine diphosphate D-glucuronic acid carboxylase II. Arch Biochem Biophys 170: 82–91
Hanna R, Picken M, Mendicino J (1973) Purification of a specific D-apiitol dehydrogenase from a micrococcus isolated from the surface of germinating parsley seeds. Biochim Biophys Acta 315: 259–271
Hanson B, Johannson I, Lindberg B (1966) A disaccharide dibenzoate from Daviesia latifolia. Acta Chem Scand 20: 2358–2362
Hart DA, Kindel PK (1970a) Isolation and partial characterization of apiogalacturonans from the cell wall of Lemna minor. Biochem J 116: 569–579
Hart DA, Kindel PK (1970b) A novel reaction involved in the degradation of apiogalacturonans from Lemna minor and the isolation of apibiose as a product. Biochemistry 9: 2190–2196
Hattori S, Imaseki H (1959) A new glycoside in Viburnum furcatum Blume. J Am Chem Soc 81: 4424–4427
Ho PT (1979) Branched-chain sugars. Reaction of furanoses with formaldehyde: A simple synthesis of D- and L-apiose. Can J Chem 57: 381–383
Hösel W, Barz W (1970) Flavonoide aus Cicer arietinum L. Phytochemistry 9: 2053–2056
Hofheinz W, Grisebach H (1962) Biogenesis of macrolides X. The occurrence of L-mycarose in erythromycin C. Z Naturforsch 176: 852
Hulyalkar RK, Jones JKN, Perry MB (1965) The chemistry of D-Apiose, II. The configuration of D-apiose in apiin. Can J Chem 43: 2085–2091
Karrer W, Cherbuliez E, Eugster CH (1977) Konstitution und Vorkommen der organischen Pflanzenstoffe. Ergänzungsband 1, Birkhäuser, Basel, Stuttgart
Kelleher WJ, Grisebach H (1971) Hydride transfer in the biosynthesis of uridine diphosphoapiose from uridine diphospho-D-glucuronic acid with an enzyme preparation of Lemna minor. Eur J Biochem 23: 136–142
Kelleher WJ, Baron D, Ortmann R, Grisebach H (1972) Proof for the origin of the branch hydroxymethyl carbon of D-Apiose from carbon 3 of D-glucuronic acid. FEBS Lett 22: 203–204
Keller-Schierlein W, Roncari G (1962) Metabolic products of actinomycetes: XXXIII. Hydrolysis products of lankamycin, lankavose and 4-O-acetylarcanose. Helv Chim Acta 45: 138–152
Keller-Schierlein W, Roncari G (1964) Metabolic products of microorganisms. XLVI. Constitution of lankamycin. Helv Chim Acta 47: 78–103
Kimata K, Suzuki S (1966) Studies on cytidine diphosphate glucose pyrophosphorylase and related enzymes of Azotobacter vinelandii. J Biol Chem 241: 1099–1113
Kindel PK, Watson RR (1973) Synthesis, characterization and properties of uridine 5′-(α-D-apio-D-furanosyl pyrophosphate). Biochem J 133: 227–241
Korzybski TG (1967) Antibiotics. Polish Sei Publ, Warzawa; Pergamon Press, Oxford Kreuzaler F, Hahlbrock K (1973) Flavonoid glycosides from illuminated cell suspension cultures of Petroselinum hortense. Phytochemistry 12: 1149–1152
Kreuzaler F, Hahlbrock K (1973) Flavonoid glycosides from illuminated cell suspension cultures of Petroselinum hortense. Phytochemistry 12:1149–1152
Lettau R (1969) Untersuchungen zur Verbreitung der Apiose in der Zellwand von grünen Pflanzen. Staatsexamensarbeit, Technical Univ Munich
Maier W, Matern U, Grisebach H (1975) On the role of dihydrostreptomycin in streptomycin biosynthesis. FEBS Lett 49: 317–319
Malhotra A, Murti WS, Seshadri TR (1965) Isolation of lanceolarin, a new glycoside of biochanin-A, from the root-bark of Dalbergia lanceolaria. Tetrahedron Lett 36: 3191–3196
Mascaro LJ Jr., Kindel PK (1977) Characterization of [14C]apiogalacturonans synthesized in a cell-free system from Lemna minor. Arch Biochem Biophys 183: 139–148
Matern U, Grisebach H (1972) Studies on the biosynthesis of the branched-chain sugars from the quinocycline complex. Eur J Biochem 29:5–11
Matern U, Grisebach H (1974) Bildung eines oxoäthylverzweigten Zuckers aus Thymidin- diphosphatglucose und Pyruvat mit einem zellfreien System aus Streptomyces aureofaciens. Z Naturforsch 29 c: 407–413
Matern U, Grisebach H (1977) UDP-apiose/UDP-xylose synthase. Subunit composition and binding studies. Eur J Biochem 74: 303–312
Matern U, Grisebach H, Karl W, Achenbach H (1972) Structure of the sugar components of the quinocycline complex. Eur J Biochem 29: 1–4
Matern H, Brillinger GU, Pape H (1973) Stoffwechselprodukte von Mikroorganismen 114. Thymidin-diphospho-D-glucose-oxidoreduktase aus Streptomyces rimosus. Arch Mikrobiol 88: 37–48
Mayer W, Kunz W (1959) Über ein zweites Vorkommen von Hamamelitannin. Naturwissenschaften 46: 206–207
Mayer W, Kunz W, Loebich F (1965) Die Struktur des Hamamelitannins. i 688: 232–238
McNeil M, Darvill AG, Albersheim P (1979) The structural polymers of the primary cell walls of dicots. In: Herz W, Grisebach H, Kirby GW (eds) Progress in the chemistry of organic natural products. Springer, Wien, New York, Vol. 37, pp 191–249
Melo A, Glaser L (1968) The mechanism of 6-deoxyhexose synthesis II. J Biol Chem 243: 1475–1478
Melo A, Elliott WH, Glaser L (1968) The mechanism of 6-deoxyhexose synthesis I. J Biol Chem 243: 1467–1474
Mendicino J, Abou-Issa H (1974) Conversion of UDP-D-glucuronic acid to UDP-D-apiose and UDP-D-xylose by an enzyme isolated from Lemna minor. Biochim Biophys Acta 364: 159–172
Mendicino J, Hanna P (1970) The synthesis of isomers of D-abiofuranosyl 1-phosphate. J Biol Chem 245: 6113–6124
Miyamoto M, Kawamatsu Y, Shinohara M, Nakadaira Y, Nakanashi K (1966a) Structures and properties of the sugars obtained from the chromomycins. Tetrahedron 22:2785–2799 Miyamoto M, Kawamatsu Y, Kawashima K, Shinohara M, Nakanishi K (1966 b) The full structures of three chromomycins. Tetrahedron Lett 6: 545–552
Miyamoto M, Kawamatsu Y, Kawashima K, Shinohara M, Nakanishi K (1966b) The full structures of three chromomycins. Tetrahedron Lett 6:545–552
Nakaoki T, Morita N, Motosune H, Hiraki A, Takeuchi T (1955) Medicinal resources II. Components of the leaves of Sophora angustifolia, Vicia hirsuta, and Linaria japonica. Pharm Soc Jpn 75: 172–176
Neal DL, Kindel PK (1970) D-Apiose reductase from Aerobacter aerogenes. J Bacteriol 101: 910–915
Nordström CG, Swain R, Hamblin AJ (1953) Flavone glycosides of parsley. I. Isolation of 7-C-apiosylglucosyl-luteolin. Chem Ind: 85
Ohta N, Tagishita K (1970) Isolation and structure of new flavonoids, flavoyadorinin A., flavoyadorinin B and homoflavoyadorinin B, in the leaves of Viscum album var. coloratum epiphyting to Pyrus communis (pear). Agr Biol Chem 34: 900–907
Okuda S, Suzuki N, Suzuki S (1967) Isolation and structure of cytidine diphosphate-6-deoxy- 3-C-methyl-2-O-methyl-L-aldohexopyranoside (cytidine diphosphate vinelose) from Azotobacter vinelandii. J Biol Chem 242: 958–966
Okuda S, Suzuki N, Suzuki S (1968) Biosynthesis of branched chain deoxysugars. J Biol Chem 243: 6353–6360
Ortmann R, Sandermann H Jr., Grisebach H (1970) Transfer of apiose from UDP-apiose to 7-O-(ß -D-glucosyl)-apigenin and 7-0-(ß-D-glucosyl)-chrysoeriol with an enzyme preparation from parsley. FEBS Lett 7: 164–166
Ortmann R, Sutter A, Grisebach H (1972) Purification and properties of UDP-apiose: 7-0-(ß-D-glucosyl)-flavone apiosyltransferase from cell suspension cultures of parsley. Biochim Biophys Acta 289: 293–302
Ortmann R, Matern U, Grisebach H, Stadler P, Sinnwell V, Paulsen H (1974) NADPH- dependent formation of thymidine-diphosphodihydrostreptose from thymidine-diphospho-D-glucose in a cell-free system from Streptomyces griseus and its correlation with streptomycin biosynthesis. Eur J Biochem 43: 265–271
Overend G, Williams NR (1965) Branched-chain sugars IV. The synthesis of D-hamamelose and D-epihamamelose. J Chem Soc: 3446–3448
Ovodov YS, Ovodova RG, Bondarenko OD, Krasikova IN (1971) Pectic substances of Zosteraceae IV. Pectinase digestion of zosterine. Carbohydr Res 18: 311–318
Ovodova RG, Vaskovsky VE, Ovodov YS (1968) The pectic substances of Zosteraceae. Carbohydr Res 6: 328–332
Pan YT, Kindel PK (1977) Characterization of particulate D-apiosyl- and D-xylosyl-transferase from Lemna minor. Arch Biochem Biophys 183: 131–138
Pape H, Brillinger G (1973) Stoffwechselprodukte von Mikroorganismen 113. Biosynthese von Thymidin-diphosphomycarose durch ein zellfreies System aus Streptomyces rimosus. Arch Mikrobiol 88: 25–35
Pape H, Schmid R, Grisebach H, Achenbach H (1969) Übertragung der intakten Methylgruppe des Methionins bei der Biosynthese der L-mycarose. Eur J Biochem 10: 479–483
Patrick AD (1956) Occurrence of apiose in Hevea brasiliensis. Nature (London) 178: 216
Paulsen H, Redlich H (1974) Synthese der vier isomeren Methyl-D-aldgaroside. Strukturermittlung des Methylaldgarosids B aus Aldgamycin E. Chem Ber 107:2992–3012 Paulsen H, Sinnwell V, Stadler P (1972) Synthese verzweigter Kohlenhydrate mit Aldehyd-Seitenkette - Einfache Synthese von L-Streptose und D-Hamamelose. Angew Chem 84: 112–113
Paulsen H, Sinnwell V, Stadler P (1972) Synthese verzweigter Kohlenhydrate mit Aldehyd-Seitenkette - Einfache Synthese von L-Streptose und D-Hamamelose. Angew Chem 84:112–113
Paulsen H, Roden K, Sinn well V, Koebernick W (1977) Einfache Synthese der Pillarose. Chem Ber 110: 2146–2149
Pezzanite JO, Chardy J, Lau PY, Wood G, Walker DL, Fraser-Reid B (1975) A revised structure for the antibiotic pillaromycin A. J Am Chem Soc 97: 6250–6251
Picken JM, Mendicino J (1967) The biosynthesis of D-apiose in Lemna minor. J. Biol Chem 242: 1629–1634
Ragoonwala R, Friedrich H (1967) Über das Vorkommen von Flavonglykosiden in Capsicum-Pflanzen. Naturwissenschaften 54: 368
Rahman AU (1958) Über das Vorkommen von Apiin in Sellerie. Z Naturforsch 13 b:201–202
Rappaportt J, Giacopello D, Seldes AM, Blanco MC, Deulofeu V (1977) Phenolic glycosides from Solanum glaucophyllum: A new quercetin triglycoside containing D-apiose. Phytochemistry 16: 1115–1116
Reimann H, Jaret RS, Cooper DJ (1971) Sisomicin: Stereochemistry and attachment of the unsaturated sugar moiety. Chem Commun: 924–925
Roberts RM, Shah RH, Loewus F (1967) Inositol metabolism in plants IV. Biosynthesis of apiose in Lemna and Petroselinum. Plant Physiol 42: 659–666
Sandermann H Jr., Grisebach H (1968) Zur Biosynthese der Apiose 3. Untersuchungen über das Vorkommen von UDP-Apiose und anderer UDP-Zucker in Petersilie (Apium petroselinum L.). Eur J Biochem 6: 404–410
Sandermann H Jr., Tisue GT, Grisebach H (1968) Biosynthesis of D-apiose IV. Formation of UDP-apiose from UDP-D-glucuronic acid in cell-free extracts of parsley (Apium petroselinum L.) and Lemna minor. Biochim Biophys Acta 165: 550–552
Scherpenberg H van, Gröbner W, Kandier O (1965) Zur Physiologie und zum Vorkommen der Hamamelose. Festschrift K. Mothes 65. Geburtstag, Gustav Fischer, Jena: 387–406
Schildknecht H, Tansher B, Moeschier H, Edelmann J (1978) Detection and structure elucidation of leaf movement factors from Mimosaceae. Proc 11th Int Symp Chem Nat Prod Part I, Vol. 4, Bulgarian Acad Sci, Sofia: 97–111
Schilling G, Keller A (1977) Zusammensetzung und Konformation von Hamamelose in Lösung. Ann Chem: 1475–1479
Schmid R, Grisebach H (1970a) Zur Biosynthese der D-Aldgarose. Eur J Biochem 14: 243–252
Schmid R, Grisebach H (1970b) Zur Biosynthese der D-Aldgarose II. Nauforsch 25 b: 1259–1263
Schmidt OT (1929) Über Zucker mit verzweigter Kohlenstoffkette I. Die Konstitution des Zuckers aus Hamameli-tannin. Ann Chem 476: 250–269
Schmidt OT (1930) Über Zucker mit verzweigter Kohlenstoffkette II. Konstitution und Konfiguration von Apiose. Ann Chem 483: 115–123
Schmidt OT, Heintz K (1934) Über Zucker mit verzweigter Kohlenstoffkette V. Die Synthese der Hamamelonsäure. Ann Chem 515: 77–96
Schmidt OT, Weber-Molster CC (1934) Über Zucker mit verzweigter Kohlenstoffkette IV. Das optische Verhalten der Aldonsäuren in Gegenwart von Natriummolybdat. Ann Chem 515: 65–76
Sellmair J, Kandier O (1970) Zur Physiologie von Hamamelose und Hamamelit in Primula clusiana Tausch. Z Pflanzenphysiol 63: 65–83
Sellmair J, Beck E, Kandier O (1968) Isolierung und Identifizierung von Hamamelit aus Primula clusiana Tausch. Z Pflanzenphysiol 59: 70–79
Sellmair J, Beck E, Kandier O, Kress A (1977) Hamamelose and its derivatives as chemotaxonomic markers in the genus Primula. Phytochemistry 16: 1201–1204
Seshadri TR, Vydeeswaran S (1971) Cucurbitaceae, chemical examination of Luffa echinata. Phytochemistry 10: 667–669
Shafizadeh F (1956) Branched-chain sugars of natural occurrence. Adv Carbohydr Chem 11: 263–283
Subramanian SS, Nagarajan S (1970) Flavonoids of three Crotalaria species. Phytochemistry 9: 2581–2584
Thanbichler A (1973) Über den Metabolismus der Hamamelose. Thesis, Univ Munich
Thanbichler A, Beck E (1974) Catabolism of hamamelose. The anaerobic dissimilation of D-hamamelose by Kluyvera citrophila 627. Eur J Biochem 50: 191–196
Thanbichler A, Gilck H, Beck E (1971) Über den Katabolismus von Hamamelose [2-C- (Hydroxymethyl)-D-ribose]. I. Die Oxidation von Hamamelose durch Pseudomonas. Z Naturforsch 26 b: 912–915
Umezawa H (1967) Index of antibiotics from actinomycetes. Univ Tokyo Press, Tokyo; Univ Park Press, State Coll, Pa
Vongerichten E (1901) Über Apiin und Apiose. Ann Chem 318: 121–136
Vongerichten E (1902) Über Apiose, eine ß-Oxymethylerythrose. Ann Chem 321: 71–83
Wagner H, Demuth G (1972) 6-O-(D-Apiofuranosyl)-1,6,8-Trihydroxy-3-Methyl-Anthrachi- non, ein neues Glykosid (Frangulin B) aus der Rinde von Rhamnus frangula L. Tetrahedron Lett 49: 5013–5014
Wagner H, Demuth G (1974) Anthraquinone glycosides from Rhamnus frangula: 6-0-Apiofuranosyl-1,6,8-trihydroxy-3-methylanthraquinone. Z Naturforsch 29 c:204–208
Wagner H, Kirmayer W (1957) Uber das Vorkommen von Apigeninglykosiden in einigen Kompositenblüten. Naturwissenschaften 44: 307
Wahl HP, Matern U, Grisebach H (1975) Two enzymes in Streptomyces griseus for the synthesis of dTDP-L-dihydrostreptose from dTDP-6-deoxy-D-xylo-4-hexosulose. Biochem Biophys Res Commun 64: 1041–1045
Walker DL, Fraser-Reid B (1975) Syntheses of “supposed” and “real” pillarose. J Am Chem Soc 97: 6251–6253
Watson RR, Kindel PK (1970) Enzymatic synthesis of apiin from UDP-D-apiose-14C and 0-ß-D-glucopyranosyl-(l→7)-apigenin. Plant Physiol 46 S:27
Watson RR, Orenstein NS (1975) Chemistry and biochemistry of apiose. Adv Carbohydr Chem Biochem 31: 135–184
Wellmann E, Grisebach H (1971) Purification and properties of an enzyme preparation from Lemna minor catalyzing the synthesis of UDP-apiose and UDP-D-xylose from UDP-D-glucuronic acid. Biochim Biophys Acta 235: 389–397
Wellmann E, Baron D, Grisebach H (1971) Two different enzymes for the biosynthesis of UDP-xylose from UDP-glucuronic acid in cell suspension cultures of parsley. Biochim Biophys Acta 244: 1–6
Wieczorek J (1976) Anreicherung und Charakterisierung der Enzyme des Hamamelosekatabolismus. Thesis, Univ Munich
Wiley PF, MacKellar FA, Caron EL, Kelly RB (1968) Isolation, characterization and degradation of nogalamycin. Tetrahedron Lett 6: 663–668
Wiley PF, Duchamp DJ, Hsiung V, Chidester CG (1971) The structure, absolute configuration and chemistry of nogalose. J Org Chem 36: 2670–2673
Williams DT, Jones JKN (1964) The chemistry of apiose, Part I. Can J Chem 42: 69–72
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1982 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Beck, E. (1982). Branched-Chain Sugars. In: Loewus, F.A., Tanner, W. (eds) Plant Carbohydrates I. Encyclopedia of Plant Physiology, vol 13 / A. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68275-9_4
Download citation
DOI: https://doi.org/10.1007/978-3-642-68275-9_4
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-68277-3
Online ISBN: 978-3-642-68275-9
eBook Packages: Springer Book Archive