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The use of the Nbb-resin for the solid-phase synthesis of peptide alkylesters and alkylamides. Synthesis of leuprolide

✍ Scribed by Ernesto Nicolás; Javier Clemente; Tina Ferrer; Fernando Albericio; Ernest Giralt

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
809 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

The use ofnucleophiles for the cleavage of an o-nitrobenzylester peptide-resin bond in order to afford peptide alkylesters and alkylamides has been studied. With this purpose, three short peptide sequences anchored to a Nbb-resin were used as models. Peptides were cleaved from the polymeric supports by reaction with primary and secondary amines and by a transesterification process with yields that depended on the nucleophile and the C-terminal amino acid of the sequence. This methodology was applied to the synthesis of leuprolide, an ethylamide peptide of relevant pharmacological interest, which was obtained in a 70% overall yield.

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