RSC Advances

Epoxy amino acids produced from allylglycines intramolecularly cyclised to yield four stereoisomers of 4-hydroxyproline derivatives

S Krishnamurthy, T Arai, K Nakanishi, N Nishino

Index: Krishnamurthy, Suvratha; Arai, Toru; Nakanishi, Kanae; Nishino, Norikazu RSC Advances, 2014 , vol. 4, # 5 p. 2482 - 2490

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Citation Number: 5

Abstract

Derivatives of 2-amino-4-pentenoic acid (allylglycine) were efficiently resolved using Subtilisin or acylase. The side-chain unsaturated bond of the enantiomerically pure amino acid with tert-butoxycarbonyl (Boc) protection was smoothly epoxidized with m- chloroperbenzoic acid. When the Boc protection of the amino group was removed, the amino group intramolecularly attacked the side-chain epoxide, generating compounds ...