ISSN:
1573-3904
Keywords:
Aza-peptides
;
Benzodiazepine-like peptide
;
Iminoaza-peptides
;
Pseudopeptides
;
Reduced aza-peptides
;
Triphosgene
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF02442879
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