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Synthèse du glycyl‐N ϵ ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valyl‐glycyl‐N ϵ ‐CBO‐L‐lysyl‐N ϵ ‐CBO‐L‐lysyl‐L‐arginyl‐L‐arginyl‐L‐prolyl‐L‐valinate de méthyle, un peptide représentant la séquence 10 à 20 de l'ACTH
Author(s) -
Boissonnas R. A.,
Guttmann St.,
Jaquenoud P.A.,
Sandrin Ed.,
Waller J.P.
Publication year - 1961
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.19610440117
Subject(s) - chemistry , valine , lysine , stereochemistry , amino acid , biochemistry
N‐CBO‐ L ‐arginyl‐ L ‐arginine is condensed with L ‐prolyl‐ L ‐valine methyl ester and, after splitting of the CBO group, L ‐arginyl‐ L ‐arginyl‐ L ‐prolyl‐ L ‐valine methyl ester is obtained. This is condensed with N‐trityl‐glycyl‐N ϵ ‐CBO‐ L ‐lysyl‐N ϵ ‐CBO‐ L ‐lysine and, after selective splitting of the trityl group, glycyl‐N ϵ ‐CBO‐ L ‐lysyl‐N ϵ ‐CBOL‐ lysyl‐ L ‐arginyl‐ L ‐arginyl‐ L ‐prolyl‐ L ‐valine methyl ester is obtained. Condensation of this heptapeptide with N‐trityl‐glycyl‐N ϵ ‐CBO‐ L ‐lysyl‐ L ‐prolyl‐ L ‐valine yields an endecapeptide, which, after selective splitting of the trityl group, is converted into the trihydrochloride of glycyl‐N ϵ ‐CBO‐ L ‐lysyl‐ L ‐prolyl‐ L ‐valyl‐glycyl‐N ϵ ‐CBO‐ L ‐ lysyl‐N ϵ ‐CBO‐ L ‐lysyl‐ L ‐arginyl‐ L ‐arginyl‐ L ‐prolyl‐ L ‐valine methyl ester. The identity, the chemical purity and the optical homogeneity of this endecapeptide is evidenced by elementary and amino acid analyses, by chromatography and electrophoresis on paper, and by enzymatic degradation.