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 support of three aza-, iminoaza- and reduced aza-peptide homologues is described. From the same hydrazinocarbonyl peptide-PAM precursor, the coupling of either a Boc-amino acid or a Boc-amino aldehyde gives rise to an aza-peptide or an iminoaza-peptide, containing the Cα-CO-NH-Nα-CO-NH-Cα or Cα-CH=N-Nα-CO-NH-Cα surrogate, of the peptide motif, respetively. In situ reduction of the latter by NaBH3CN leads to a reduced aza-peptide containing the Cα-CH2-NH-Nα-CO-NH-Cα moiety. The key step synthesis of the hydrazinocarbonyl peptide-PAM precursor is carried out by coupling on the growing peptide chain theN-Boc-azaamino acid chloride obtained by the action of triphosgene on the, correspondingN-Boc-hydrazine. These modifications have been introduced in position 1–2 of the YLGYLEQLLR benzodiazepine-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.10.1007/bf02442879

    DOI

    http://dx.doi.org/10.1007/bf02442879

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1048250561


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