A solid-phase synthesis of three aza-, iminoaza- and reduced aza-peptides from the same precursor View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1997-12

AUTHORS

Céline Frochot, Régis Vanderesse, Alain Driou, Guy Linden, Michel Marraud, Manh Thong Cung

ABSTRACT

Using 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... »

PAGES

219-225

References to SciGraph publications

  • 1995-11. Synthesis and conformational analysis of AzAsx-containing oligopeptides in INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS
  • 1997-12. Conformational studies of a benzodiazepine-like peptide in SDS micelles by circular dichroism,1H NMR and molecular dynamics simulation in INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1023/a:1008826901053

    DOI

    http://dx.doi.org/10.1023/a:1008826901053

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1004596085


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