Quantitative acylation of amino compounds catalysed by penicillin G acylase in organic solvent at controlled water activity

Alessandra Basso, Stefania Biffi, Luigi De Martin, Lucia Gardossi, Paolo Linda

Research output: Contribution to journalArticle

Abstract

Covalently immobilised penicillin G acylase (PGA-450) accepts in toluene, at controlled water activity (aw), a broad range of amino compounds as nucleophiles in kinetically controlled acylation. Hydrolytic reactions were prevented and complete conversions were achieved in short times even when working with an equimolar concentration of the substrates. The recovery of the products was facile, leading to high isolation yields. The obtained N-acylated derivatives of L-amino acids can be used in further reactions, since no purification steps are required in such conditions. This opens new perspectives to the application of PGA in selective protection of the amino function for peptide synthesis. All attempts to perform esterification and transesterification reactions with PGA in toluene, at the same aw as used for the acylation of amino compounds, were unsuccesful.

Original languageEnglish
Pages (from-to)757-762
Number of pages6
JournalCroatica Chemica Acta
Volume74
Issue number4
Publication statusPublished - Nov 2001

Keywords

  • Acylation
  • Derivatised L-amino acids
  • Kinetically controlled synthesis
  • Organic solvent
  • Penicillin G acylase
  • Water activity

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Quantitative acylation of amino compounds catalysed by penicillin G acylase in organic solvent at controlled water activity'. Together they form a unique fingerprint.

  • Cite this