CaltechAUTHORS
  A Caltech Library Service

Enantioseparation and identification for the rationalization of the environmental impact of 4 polychlorinated biphenyls

Guo, Fangjie and Tang, Qiaozhi and Xie, Jingqian and Zhao, Lu and Liu, Kai and Liu, Weiping (2018) Enantioseparation and identification for the rationalization of the environmental impact of 4 polychlorinated biphenyls. Chirality, 30 (4). pp. 475-483. ISSN 0899-0042. http://resolver.caltech.edu/CaltechAUTHORS:20180116-153707924

[img] MS Word (Figure S1; Tables S1-S2) - Supplemental Material
See Usage Policy.

96Kb

Use this Persistent URL to link to this item: http://resolver.caltech.edu/CaltechAUTHORS:20180116-153707924

Abstract

Polychlorinated biphenyls (PCBs) are harmful and persistent organic pollutants that have long been used in industrial manufacturing. Their persistence leads to accumulation in the food chain causing potential toxic effects. As 19 out of 78 of the chiral congeners have stable atropisomers at ambient temperature, we studied some typical enantiomers: PCB45, PCB95, PCB136, and PCB149. The chiral stationary phases OD-H and OJ-H were used for separation in analytic high-performance liquid chromatography (HPLC), as well as for collection in semi-preparative HPLC. The resolution was optimized with respect to n-hexane–based mobile phases, temperature, and flow rate. All pure enantiomers were recovered from semi-preparative HPLC within 15 minutes for practical purpose. Characterization of the absolute configurations were conducted with a combination of theoretical and experimental electronic circular dichroism measurements. The enantiomers of PCB45, PCB95, PCB136, and PCB149 proved to be eluted as R > S, S > R, R > S, and S > R, respectively. Molecular structures (eg, substituent groups) and properties (eg, bond lengths, bond angles, and dipole moments) were quantitatively analyzed to understand the toxicity effect of PCBs. In summary, we have developed a well-established methodology of collection and configuration identification for analogous PCB derivatives.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/chir.22811DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/chir.22811/abstractPublisherArticle
ORCID:
AuthorORCID
Liu, Kai0000-0002-2109-8196
Liu, Weiping0000-0002-1173-892X
Additional Information:© 2018 Wiley Periodicals, Inc. Issue Online 26 March 2018; Version of Record online: 08 January 2018; Manuscript accepted: 18 July 2017; Manuscript revised: 12 July 2017; Manuscript received: 08 May 2017. The authors acknowledge financial support from the National Natural Science Foundation of China (221427815 and 21320102007).
Funders:
Funding AgencyGrant Number
National Natural Science Foundation of China221427815
National Natural Science Foundation of China21320102007
Subject Keywords:collection; electronic circular dichroism; enantioseparation; in silico; polychlorinated biphenyl
Record Number:CaltechAUTHORS:20180116-153707924
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20180116-153707924
Official Citation:Guo F, Tang Q, Xie J, Zhao L, Liu K, Liu W. Enantioseparation and identification for the rationalization of the environmental impact of 4 polychlorinated biphenyls. Chirality. 2018;30:475–483. https://doi.org/10.1002/chir.22811
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:84346
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:17 Jan 2018 19:03
Last Modified:09 Apr 2018 16:05

Repository Staff Only: item control page