Premium
Study on the metabolic mechanism of chiral inversion of S ‐Mandelic acid in vitro
Author(s) -
Gao LingBo,
Wang JinZhao,
Yao TongWei,
Zeng Su
Publication year - 2012
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.21031
Subject(s) - chemistry , mandelic acid , enantiomer , hydrolysis , chirality (physics) , in vitro , phosphonate , in vivo , thioester , stereochemistry , inversion (geology) , biochemistry , organic chemistry , enzyme , chiral symmetry breaking , physics , microbiology and biotechnology , quantum mechanics , nambu–jona lasinio model , biology , quark , paleontology , structural basin
Mandelic acid (MA) is generally used as a biological indicator of occupational exposure to styrene, which is classified as a class of hazardous environmental pollutants. It was found to undergo one‐directional chiral inversion ( S ‐MA to R ‐MA) in Wistar and Sprague‐Dawley rats in vivo . This study was aimed to explore the metabolic mechanism of chiral inversion of S ‐MA in vitro . S ‐MA was converted to R ‐MA in rat hepatocytes, whereas MA enantiomers remained unchanged in acidic and neutral phosphate buffers, HepG2 cells, and intestinal flora. In addition , the synthesized S ‐MA‐CoA thioester was rapidly racemized and hydrolyzed to R ‐MA by rat liver homogenate and S9, cytosolic and mitochondrial fractions. The data suggest that chiral inversion of S ‐MA may involve the hydrolysis of S ‐MA‐CoA, and its metabolic mechanism could be the same as that of 2‐arylpropionic acid (2‐APA) drugs. Chirality 24:86–95, 2012. © 2011 Wiley Periodicals, Inc.