Penicillin acylase-catalyzed peptide synthesis in aqueous medium: A chemo-enzymatic route to stereoisomerically pure diketopiperazines

Andrei Y. Khimiuk, Alexei V. Korennykh, Luuk M. Van Langen, Fred Van Rantwijk, Roger A. Sheldon, Vytas K. Švedas

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

A range of non-natural dipeptides of the general formula D-(-)-phenylglycyl-L-X, where X is a natural α-amino acid, have been prepared by penicillin acylase-catalyzed synthesis in aqueous medium from D-(-)-phenylglycine amide and the corresponding amino acids. The conversion of the dipeptides to the corresponding dipeptide esters, followed by their subsequent spontaneous cyclization afforded the corresponding stereoisomerically pure diketopiperazines.

Original languageEnglish (US)
Pages (from-to)3123-3128
Number of pages6
JournalTetrahedron Asymmetry
Volume14
Issue number20
DOIs
StatePublished - Oct 17 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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