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An alternative total synthesis of pentosidine
Author(s) -
Liu Yahua,
Zhang Weihan,
Sayre Lawrence M.
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.611
Subject(s) - chemistry , pentosidine , pyridine , hydantoin , glycation , alkylation , amination , reductive amination , lysine , regioselectivity , amino acid , ornithine , oxidative stress , organic chemistry , biochemistry , arginine , receptor , catalysis
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).