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A Convenient Method for the Stereoselective Conversion of Aryl Peptidyl Ketones into the Corresponding Aryl Aminomethin Derivatives, A Novel Class of Modified Peptides

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Abstract:

In this paper we describe a reductive amination procedure that can be employed in the preparation of a novel class of pseudopeptides in which a specific amide bond is replaced by a CH(Ar)NH group. The developed methodology, performed using NaBH3CN and TiCl4, is characterized by the formation of diastereomeric intermediates in a relative 1:1 ratio. It provides aryl aminomethin pseudopeptides in moderate but satisfactory yields and with definite stereochemistry on the asymmetric centres next to the modified peptide bond.

Keywords: aryl aminomethin peptides; aryl peptidyl ketones; pseudopeptides; sodium cyano borohydride; titanium tetrachloride

Document Type: Review Article

DOI: https://doi.org/10.2174/0929866053765725

Affiliations: Dipartimento di Scienze Farmaceutiche, Universita degli Studi della Calabria, Via Ponte P. Bucci, Cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.

Publication date: 2005-05-01

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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