A solid-phase synthesis of three aza-, iminoaza- and reduced aza-peptides from the same precursor |
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Authors: | Céline Frochot Régis Vanderesse Alain Driou Guy Linden Michel Marraud and Manh Thong Cung |
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Institution: | (1) LCPM, CNRS-URA 494, ENSIC-INPL, BP 451, F-54001 Nancy Cedex, France;(2) LBSA, Unité associée à l'INRA, Université Henri Poincaré, BP 239, F-54506 Vandoeuvre lès Nancy Cedex, France |
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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 theC -CO-NH-N -CO-NH-C orC -CH=N-N -CO-NH-C surrogate of the peptide motif, respectively. In situreduction of the latter by NaBH3CN leads to a reducedaza-peptide containing theC -CH2-NH-N -CO-NH-C 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 |
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Keywords: | Aza-peptides Benzodiazepine-like peptide Iminoaza-peptides Pseudopeptides Reduced aza-peptides Triphosgene |
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