Tetrahedron

Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer

S Pétursson, JE Baldwin

Index: Petursson, Sigthor; Baldwin, Jack E. Tetrahedron, 1998 , vol. 54, # 22 p. 6001 - 6010

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Citation Number: 10

Abstract

The paper describes the synthesis of two epimeric tripeptides δ-(l-α-aminoadipoyl)-l- cysteinyl-d-(O-methyl)-d-threonine (13) and δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d- allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The d- allothreonine tripeptide (14) has been shown to be an excellent substrate for the enzyme whereas the d-threonine epimer did not react at all. The compound formed by the enzyme ...