Efficient enzymatic routes for the synthesis of new eight-membered cyclic β-amino acid and β-lactam enantiomers

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5 Citations (Scopus)

Abstract

Efficient enzymatic resolutions are reported for the preparation of new eight-membered ring-fused enantiomeric β-amino acids [(1R, 2S)-9 and (1S, 2R)-9] and β-lactams [(1S, 8R)-3, (1R, 8S)-3 (1S, 8R)-4 and (1R, 8S)-7], through asymmetric acylation of (±)-4 (E > 100) or enantioselective hydrolysis (E > 200) of the corresponding inactivated (±)-3 or activated (±)-4 β-lactams, catalyzed by PSIM or CAL-B in an organic solvent. CAL-B-catalyzed ring cleavage of (±)-6 (E > 200) resulted in the unreacted (1S, 8R)-6, potential intermediate for the synthesis of enantiomeric anatoxin-a. The best strategies, in view of E, reaction rate and product yields, which underline the importance of substrate engineering, are highlighted.

Original languageEnglish
Article number2211
JournalMolecules
Volume22
Issue number12
DOIs
Publication statusPublished - dec. 2017

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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