α-Vinylic amino acids: occurrence, asymmetric synthesis, and biochemical mechanisms

David B. Berkowitz, Bradley D. Charette, Kannan R. Karukurichi, Jill M. McFadden

Research output: Contribution to journalReview article

48 Scopus citations

Abstract

This report presents an overview of the family of naturally occurring 'vinylic' amino acids, namely those that feature a C-C double bond directly attached to the α-carbon, along the side chain. Strategies that have been brought to bear on the stereocontrolled synthesis of these olefinic amino acids are surveyed. The mechanistic diversity by which such 'vinylic triggers' can be actuated in a PLP (pyridoxal phosphate) enzyme active site is then highlighted by discussion of vinylglycine (VG), its substituted congeners, particularly AVG [4E-(2′-aminoethoxy)vinylglycine], and a naturally occurring VG-progenitor, SMM [(S)-methylmethionine].

Original languageEnglish (US)
Pages (from-to)869-882
Number of pages14
JournalTetrahedron Asymmetry
Volume17
Issue number6
DOIs
StatePublished - Mar 20 2006

ASJC Scopus subject areas

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

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