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

Authors

David B. Berkowitz, University of Nebraska - LincolnFollow
Bradley D. Charette, University of Nebraska - Lincoln
Kannan Karukurichi, University of Nebraska - Lincoln
Jill M. McFadden, University of Nebraska - Lincoln

Date of this Version

April 2006

Comments

Published in Tetrahedron: Asymmetry 17:6 (March 20, 2006), pp. 869–882. Copyright © 2006 Elsevier Ltd. Used by permission. http://www.sciencedirect.com/science/journal/09574166

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 stereo-controlled 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].