Absolute configuration of atropisomeric polychlorinated biphenyl 183 enantiomerically enriched in human samples.

J Phys Chem A

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan.

Published: September 2012

AI Article Synopsis

  • PCBs are persistent environmental pollutants that can accumulate in living organisms and pose health risks.
  • Out of 209 PCB congeners, 19 are chiral, with some being highly chlorinated and resistant to biological breakdown.
  • The study successfully identified the absolute configurations of important chiral PCBs (183, 171, and 132) using theoretical and experimental methods, enhancing understanding of how these compounds behave in the environment.

Article Abstract

Polychlorinated biphenyls (PCBs) are still of serious concern as a potential health hazard due to their persistency and bioacumulation. Of 209 possible PCB congeners, with varying number and position of chlorine atom(s), 19 are chiral. These are mostly highly chlorinated and tend to remain longer against the biological decompositions, suffering biological deracemization in the environment. In this work, we have unequivocally determined the absolute configurations of important chiral PCBs 183 and 171, as well as 132, through the combined theoretical and experimental investigations of the chiroptical properties (circular dichroism and optical rotation), which will be valuable in elucidating the mechanism of biological enantiomer enrichment of PCBs in the environment.

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Source
http://dx.doi.org/10.1021/jp306363nDOI Listing

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