Synthèse du N‐acétyl‐<scp>L</scp>‐séryl‐<scp>L</scp>‐tyrosyl‐<scp>L</scp>‐séryl‐<scp>L</scp>‐méthionyl‐γ‐<scp>L</scp>‐glutamate de benzyle et de peptides apparentés

Abstract

Abstract N‐CBO‐ L ‐Seryl‐ L ‐tyrosyl‐ L ‐serine methyl ester and L ‐methionyl‐γ‐benzyl‐ L ‐glutamate are prepared by different methods. Condensation by the hydrazideazide procedure affords N‐CBO‐ L ‐seryl‐ L ‐tyrosyl‐ L ‐seryl‐ L ‐methionyl‐γ‐benzyl‐ L ‐glutamate, which is shown to be optically pure by leucine‐aminopeptidase digestion. Transformation of the above N‐CBO‐tripeptide ester to the N‐acetyltripeptide ester and condensation by the hydrazide‐azide procedure with the above dipeptide gives N‐acetyl‐ L ‐seryl‐ L ‐tyrosyl‐ L ‐seryl‐ L ‐methionyl‐γ‐benzyl‐ L ‐glutamate. The effects produced in the course of fissure of CBO‐ and benzyl‐groups from peptides containing serine and methionine residues, using HBr and acetic acid, are studied.