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Highly Stereoselective Conversion of Aryl Peptidyl Ketones into the Corresponding Peptide Alcohols
Author(s) -
Di Gioia Maria Luisa,
Leggio Antonella,
Le Pera Adolfo,
Liguori Angelo,
Siciliano Carlo
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300563
Subject(s) - chemistry , stereoselectivity , diastereomer , peptide , aryl , residue (chemistry) , reactivity (psychology) , amino acid , hydride , combinatorial chemistry , peptide synthesis , organic chemistry , stereochemistry , catalysis , hydrogen , biochemistry , medicine , alkyl , alternative medicine , pathology
In this paper we describe the conversion of aryl peptidyl ketones, by a hydride reduction, into the corresponding peptide alcohols. The developed methodology is highly stereoselective and represents a very important application in peptide chemistry for obtaining peptide alcohols. It provides peptide alcohols with definite stereochemistry and in moderate, but satisfactory, yields. The reducing procedure, performed with NaBH 3 CN and TiCl 4 , probably proceeds via two diastereomeric cyclic intermediates that show different reactivity. The stereochemistry of the resulting alcohols was established after obtaining them by an alternative synthetic procedure. Furthermore, the methodology adopted keeps the urethane protecting group on the amino function of the N‐terminal amino acid residue. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)