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Studies on the racemization of a stereolabile 5‐aryl‐thiazolidinedione
Author(s) -
Welch Christopher J.,
Kress Michael H.,
Beconi Maria,
Mathre David J.
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10180
Subject(s) - racemization , chemistry , enantiomer , agonist , chromatography , chiral column chromatography , thiazolidinedione , human plasma , aqueous solution , high performance liquid chromatography , aryl , organic chemistry , combinatorial chemistry , receptor , biochemistry , medicine , alkyl , type 2 diabetes , diabetes mellitus , endocrinology
The enantiomers of the stereolabile peroxisome proliferator‐activated receptor (PPAR) agonist, 1, were isolated by preparative chiral chromatography and their absolute configuration established using a combination of chromatographic and NMR methods. Enantiomer interconversion was investigated under a variety of conditions, with rapid racemization being observed in most solvents, including all aqueous systems studied, irrespective of pH. Rapid racemization in both dog and human plasma was confirmed by chiral HPLC with MS detection. Chirality 15:143–147, 2003. © 2003 Wiley‐Liss, Inc.