Organic letters

Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening

H Liu, VR Pattabiraman, JC Vederas

Index: Liu, Hongqiang; Pattabiraman, Vijaya R.; Vederas, John C. Organic Letters, 2007 , vol. 9, # 21 p. 4211 - 4214

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Citation Number: 33

Abstract

Regio-and stereoselective aziridine ring opening with oxygen nucleophiles derived from serine and threonine provides a route to stereochemically pure 4-oxa-2, 6-diaminopimelic acid (oxa-DAP) and its methyl-substituted derivatives. Oxa-DAP is a substrate of DAP epimerase, a key enzyme for biosynthesis of l-lysine and formation of peptidoglycan precursors. Orthogonally protected analogues of lanthionine and β-methyllanthionine ...

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