Ontology type: schema:ScholarlyArticle
1997-12
AUTHORSCéline Frochot, Régis Vanderesse, Alain Driou, Guy Linden, Michel Marraud, Manh Thong Cung
ABSTRACTUsing the Boc-strategy, a step-by-step synthesis on the PAM solid supportof three aza-, iminoaza- and reduced aza-peptide homologues is described.From the same hydrazinocarbonyl peptide-PAM precursor, the coupling ofeither a Boc-amino acid or a Boc-amino aldehyde gives rise to an aza-peptideor an iminoaza-peptide containing theCα-CO-NH-Nα-CO-NH-Cα orCα-CH=N-Nα-CO-NH-Cα surrogate of the peptide motif, respectively. In situreduction of the latter by NaBH3CN leads to a reducedaza-peptide containing theCα-CH2-NH-Nα-CO-NH-Cα moiety. The key step synthesis of thehydrazinocarbonyl peptide-PAM precursor is carried out by coupling on thegrowing peptide chain the N-Boc-aza-amino acid chloride obtained by theaction of triphosgene on the corresponding N-Boc-hydrazine. Thesemodifications have been introduced in position 1-2 of the YLGYLEQLLRbenzodiazepine-like decapeptide More... »
PAGES219-225
http://scigraph.springernature.com/pub.10.1023/a:1008826901053
DOIhttp://dx.doi.org/10.1023/a:1008826901053
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