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Synthèse de la L ‐histidyl‐ L ‐phénylalanyl‐ L ‐arginyl‐ L ‐tryptophanyl‐glycyl‐ϵ‐CBO‐ L ‐lysyl‐ L ‐prolyl‐ L ‐valylamide
Author(s) -
Boissonnas R. A.,
Guttmann St.,
Huguenin R. L.,
Jaquenoud P.A.,
Sandrin Ed.
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.19580410641
Subject(s) - chemistry , lysine , saponification , stereochemistry , amine gas treating , valine , amino acid , organic chemistry , biochemistry
Trityl‐glycyl‐ϵ‐CBO‐ L ‐lysine is condensed with L ‐prolyl‐ L ‐valine methyl ester and, after amidification and splitting of the trityl group, glycyl‐ϵ‐CBO‐ L ‐lysyl‐ L ‐prolyl‐ L ‐valylamide is obtained. This is condensed with ditrityl‐ L ‐histidyl‐ L ‐phenylalanyl‐ L ‐arginyl‐ L ‐tryptophane prepared by condensation of ditrityl‐ L ‐histidyl‐ L ‐phenylalanine with L ‐arginyl‐ L ‐tryptophane methyl ester and saponification. Dicyclohexyl‐carbodiimide is used as a condensing agent. After splitting off the trityl groups, the final octapeptide, L ‐histidyl‐ L ‐phenylalanyl‐ L ‐arginyl‐ L ‐tryptophanyl‐glycyl‐ϵ‐CBO‐ L ‐lysyl‐ L ‐prolyl‐ L ‐valylamide is shown to be optically pure by leucine‐aminopeptidase digestion.