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An alternative total synthesis of pentosidine

✍ Scribed by Yahua Liu; Weihan Zhang; Lawrence M. Sayre

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
160 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Pentosidine, a fluorescent advanced glycation endproduct that serves as a biomarker of diabetic complications, kidney dysfunction, oxidative stress, and aging and age‐related diseases, was synthesized from 2,3‐diaminopyridine and benzyloxycarbonyl (Cbz) protected chiral amino acids N^α^‐Cbz‐lysine and N^δ^‐Cbz‐ornithine. Regioselective alkylation of 2‐(methylthio)imidazo[4,5‐b]pyridine, chlorination of methylthio group, and amination of 2‐chloro‐imidazo[4,5‐b]pyridine are the key steps. Hydantoin protection of amino acids was used and the deprotection under acidic condition was achieved in the presence of glycine. J. Heterocyclic Chem., (2011).

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