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

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

Volume: 12 Issue: 4

Author(s): M. L. Di Gioia, A. Leggio, A. Le Pera, A. Liguori, A. F. Pitrelli and C. Siciliano

Affiliation:

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

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.

Cite this article as:

Gioia L. Di M., Leggio A., Pera Le A., Liguori A., Pitrelli F. A. and Siciliano C., A Convenient Method for the Stereoselective Conversion of Aryl Peptidyl Ketones into the Corresponding Aryl Aminomethin Derivatives, A Novel Class of Modified Peptides, Protein & Peptide Letters 2005; 12 (4) . https://dx.doi.org/10.2174/0929866053765725