Synthesis of (2S, 5S)-5-fluoromethylornithine; a potent inhibitor of ornithine aminotransferase

…, B Heintzelmann, K Jund, B Lesur, M Schleimer…

Index: Ducep; Heintzelmann; Jund; Lesur; Schleimer; Zimmermann Tetrahedron Asymmetry, 1997 , vol. 8, # 2 p. 327 - 335

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Citation Number: 8

Abstract

Only one of the four enantiomers of 5-fluoromethylornithine 1 was an irreversible inhibitor of ornithine aminotransferase. The active enantiomer 1a was synthesized from diaminoadipic acid 2 with a chemical diastereomeric separation and an enantiomeric resolution by hydrolysis of a phenylacetamide with benzylpenicillinase.