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Synthesis of Novel Sugar Amino Acids by Curtius Rearrangement
Author(s) -
van Well Renate M.,
Overkleeft Herman S.,
van Boom Jacques H.,
Coop Andrew,
Wang Jia Bei,
Wang Hongyan,
van der Marel Gijsbert A.,
Overhand Mark
Publication year - 2003
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.200210682
Subject(s) - curtius rearrangement , chemistry , glycosidic bond , moiety , stereochemistry , amine gas treating , amino acid , carboxylic acid , organic chemistry , biochemistry , enzyme
Sugar amino acids (SAAs) bearing an amine group on the anomeric position are a challenging class of SAAs to synthesize due to the inherent instability of glycosylamines. We developed a novel synthetic strategy towards both furanoid and pyranoid δ‐SAAs of this type, based on a Curtius rearrangement. The latter reaction, which is known to proceed with retention of configuration, was performed on carboxylic acids derived from the oxidation of glycosidic primary hydroxyls. Leu‐enkephalin analogs were prepared by replacing the Gly‐Gly moiety in the parent Leu‐enkephalin pentapeptide with the furanoid and pyranoid δ‐SAA. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)