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Reactions of an electrophilic glycine cation equivalent with grignard reagents a simple synthesis of βX-unsaturated amino acids

✍ Scribed by Arlindo L. Castelhano; Stephen Horne; Roland Billedeau; Allen Krantz

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 199 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)84549-9

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✦ Synopsis

A simple and general synthesis of a-amino acids employing vinyl and alkyl Grignard reagents with a glycine cation equivalent is described. B,v-Unsaturated a-amino acids are natural products that possess antibiotic activity and enzyme inhibitory properties. 3 Several synthetic B,T-unsaturated a-amino acids have been designed as specific irreversible inhibitors of pyridoxal phosphate dependent enzymes. 4 The parent, vinyl glycine 1, is also a useful chemical intermediate upon which to build novel functionality.5

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