A convenient method for the stereoselective conversion of aryl peptidyl ketones into the corresponding aryl aminomethin derivatives, a novel class of modified peptides.
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 NaBH(3)CN and TiCl(4), 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.
Di Gioia
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ML
Dipartimento di Scienze Farmaceutiche, Università degli Studi della Calabria, Arcavacata di Rende (CS), Italy.
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D000586:Amination; D001596:Benzylamines / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis; D007202:Indicators and Reagents / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry
D001596:Benzylamines; D001894:Borohydrides; D004151:Dipeptides; D007202:Indicators and Reagents; D007659:Ketones; D010455:Peptides; C025096:titanium tetrachloride; C030796:benzylamine; C009282:sodium cyanoborohydride; D014025:Titanium