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Synthèse du N‐acétyl‐ L ‐séryl‐ L ‐tyrosyl‐ L ‐séryl‐ L ‐méthionyl‐γ‐ L ‐glutamate de benzyle et de peptides apparentés
Author(s) -
Guttmann St.,
Boissonnas R. A.
Publication year - 1958
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19580410640
Subject(s) - chemistry , tripeptide , stereochemistry , dipeptide , glutamate receptor , peptide , biochemistry , receptor
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.