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Structural Elucidation of cis/trans Dicaffeoylquinic Acid Photoisomerization Using Ion Mobility Spectrometry-Mass Spectrometry.

Structural Elucidation of cis/trans Dicaffeoylquinic Acid Photoisomerization Using Ion Mobility Spectrometry-Mass Spectrometry.
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Zheng X, Renslow RS, Makola MM, Webb IK, Deng L, Thomas DG, Govind N, Ibrahim YM, Kabanda MM, Dubery IA, Heyman HM, Smith RD, Madala NE, Baker ES,


Zheng X, Renslow RS, Makola MM, Webb IK, Deng L, Thomas DG, Govind N, Ibrahim YM, Kabanda MM, Dubery IA, Heyman HM, Smith RD, Madala NE, Baker ES, (click to view)

Zheng X, Renslow RS, Makola MM, Webb IK, Deng L, Thomas DG, Govind N, Ibrahim YM, Kabanda MM, Dubery IA, Heyman HM, Smith RD, Madala NE, Baker ES,

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The journal of physical chemistry letters 2017 03 15() 1381-1388 doi 10.1021/acs.jpclett.6b03015

Abstract

Due to the recently uncovered health benefits and anti-HIV activities of dicaffeoylquinic acids (diCQAs), understanding their structures and functions is of great interest for drug discovery efforts. DiCQAs are analytically challenging to identify and quantify since they commonly exist as a diverse mixture of positional and geometric (cis/trans) isomers. In this work, we utilized ion mobility spectrometry coupled with mass spectrometry to separate the various isomers before and after UV irradiation. The experimental collision cross sections were then compared with theoretical structures to differentiate and identify the diCQA isomers. Our analyses found that naturally the diCQAs existed predominantly as trans/trans isomers, but after 3 h of UV irradiation, cis/cis, cis/trans, trans/cis, and trans/trans isomers were all present in the mixture. This is the first report of successful differentiation of cis/trans diCQA isomers individually, which shows the great promise of IMS coupled with theoretical calculations for determining the structure and activity relationships of different isomers in drug discovery studies.

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