Synthetic applications of aliphatic unsaturated α-H-α-amino acids

Abstract

This article provides an overview of the literature concerning synthetic applications of unsaturated aliphatic amino acids in the period May 2000 to December 2004.

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

“…[36,37] Reviews also describe applications in synthesis of peptidomimetics, [38,39] in bioconjugations [40][41][42] and surface chemistry. [43] It has been compared to the Staudinger ligation [37] and used in profiling of proteases [44] and in combinatorial drug discovery.…”

Synthesis of Enantiomerically Enriched Amino Acids Containing Acetylenic Bond in the Side-Chain Radical

“…The target α-alkyl and aryl substituted propargylglycines (7)(8)(9)(10)(11)(12)(13)(14) as well as (S)-2-aminoocta-7-en-4-ynoic acid (6) was isolated from the diastereomeric mixtures of alkylated complexes according to the standard procedure and crystallized from aqueous alcoholic solutions. The structures and absolute configuration of synthesized amino acids were established by physicochemical methods.…”

“…In the last 20 years the use of enantiomerically enriched non-protein amino acids containing different aliphatic, aromatic and heterocyclic groups in the side chain have been rapidly developing [14]. Amino acids containing unsaturated bonds in the side-chain radical occupy a special place among these compounds.…”

Synthesis of α‐Alkynyl‐β,β,β‐trifluoroalanine Derivatives by Sonogashira Cross‐Coupling Reaction

“…[2] Thus, such compounds are useful in providing a handle for a range of transformations, especially transition-metal-mediated functionalizations. [3] Among those, metal-catalyzed cross-coupling and metathesis-type reactions including acetylene metathesis [4] have become standard tools in organic synthesis. Moreover, with the advent of the "click chemistry" concept, [5] interest in acetylenic amino acids has been sharply rising.…”