Synthèse de la  L ‐histidyl‐ L ‐phénylalanyl‐ L ‐arginyl‐ L ‐tryptophanyl‐glycyl‐ϵ‐CBO‐ L ‐lysyl‐ L ‐prolyl‐ L ‐valylamide | Zendy

Boissonnas R. A. | Zendy; Guttmann St. | Zendy; Huguenin R. L. | Zendy; Jaquenoud P.A. | Zendy; Sandrin Ed. | Zendy

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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.

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