Skip to main content
SpringerLink
Log in

Resolution of DL-2-aminosuberic acid via protease-catalyzed ester hydrolysis

  • Full Papers
  • Published:
Amino Acids Aims and scope Submit manuscript

Summary

Papain-catalyzed regioselective cleavage ofα-methyl ester in Z-DL-Asu(OMe)-OMe leads to Z-L-Asu(OMe)-OH and Z-D-Asu(OMe)-OMe. Subsequent saponifications yield Z-L-Asu-OH and Z-D-Asu-OH. The enzymaticα-ester hydrolysis was also achieved by subtilisin BPN′ in organic solvent with low water content.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

Asu:

2-aminosuberic acid

Z:

benzyloxycarbonyl

OMe:

methyl ester

DCHA:

dicyclohexylamine

References

  • Čeřovský V, Jakubke H-D (1996) Nucleophile specificity of subtilisin in an organic solvent with low water content: investigation via acyl transfer reactions. Biotechnol Bioeng 49: 553–558

    Google Scholar 

  • Čeřovský V, Wünsch E, Brass H (1997) Enzymatic semisynthesis of dicarba analogs of calcitonin. Eur J Biochem 247: 231–237

    Google Scholar 

  • Hase S, Kiyoi R, Sakakibara S (1968) Synthesis of DL-α-aminosuberic acid and its optical resolution. Bull Chem Soc Jpn 41: 1266–1267

    Google Scholar 

  • Jost K, Rudinger J (1967) Amino acids and peptides. LXIX. Synthesis of two biologically active analogues of deamino-oxytocin not containing a disulphide bond. Collect Czech Chem Commun 32: 1229–1241

    Google Scholar 

  • Kitaguchi H, Ono M, Itoh I, Klibanov AM (1991) Regioselective modification of lysine's amino groups by proteases. Agric Biol Chem 55: 3067–3073

    Google Scholar 

  • Morikawa T, Munekata E, Sakakibara S, Noda T, Otani M (1976) Synthesis of eel-calcitonin and [Asu1,7]-eel-calcitonin: contribution of the disulfide bond to the hormonal activity. Experientia 32: 1104–1106

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoires des Reactions Organiques Selectives, bat. 420, Université Paris-Sud, Orsay, France

    M. Rivard

  2. Insitute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo 2, 166 10, Prague 6, Czech Republic

    P. Maloň &  V. Čeřovský

Authors
  1. M. Rivard
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. Maloň
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. Čeřovský
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rivard, M., Maloň, P. & Čeřovský, V. Resolution of DL-2-aminosuberic acid via protease-catalyzed ester hydrolysis. Amino Acids 15, 389–392 (1998). https://doi.org/10.1007/BF01320903

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01320903

Keywords

Search

Navigation