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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

✍ Scribed by Sigthór Pétursson; Jack E Baldwin

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 491 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00280-4

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✦ Synopsis

The paper describes the synthesis of two epimeric tdpeptides &(L-cx-aminoadipoyl)-L-cysteinyI-D-(Omethyl)-D-threonine (13) and &(L-ct-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 with the D-allothreonine tripeptide is a new 2-ctmethoxypenicillin.

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