Collect. Czech. Chem. Commun. 1988, 53, 2854-2856
https://doi.org/10.1135/cccc19882854

An efficient synthesis of δ-(L-α-aminoadipyl)-L-seryl-D-valine (LLD ASV), a naturally occuring tripeptide from the fermentation of Penicillium chrysogenum

Bogdan Liberek and Regina Kasprzykowska

Institute of Chemistry, University of Gdańsk, 80-952 Gdansk, Poland

Abstract

The synthesis of δ-(L-α-aminoadipyl)-L-seryl-D-valine (LLD ASV), a naturally occuring congener of the well known tripeptide δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (LLD ACV) which is the linear precursor of isopenicillin N, penicillin N, cephalosporin C is described. An efficient method for producing the requisite α-monobenzyl ester of N-benzyloxycarbonyl-L-homoglutamic acid for subsequent condesation at the side chain δ-carboxy group is presented.