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Direct observation of differences of carotenoid polyene chain cis/trans isomers resulting from structural topology.

ABSTRACT: In the present paper, trapped ion mobility spectrometry (TIMS) and theoretical calculations have been used to study carotenoid geometrical motifs generated by photoisomerization from the all-trans geometry. Multiple geometric isomers of the carotenoids lutein and zeaxanthin were separated using TIMS (R > 110) for [M](+), [M + H](+), and [M - 18](+) molecular species. Comparison of observed cross sections with those obtained from molecular dynamics calculations showed that the number of cis double bonds and s-cis single bonds in the polyene chain determine the topology space of the carotenoid. The intensities of IMS signals are correlated with the relative stability of these geometric isomers.1,2 The most stable isomer is the all-trans geometry regardless of the ionization state ([M - 18](+), [M](+), and [M + H](+)), and structural stability decreases with the increasing number of cis and/or s-cis bonds in the polyene chain.

SUBMITTER: Schenk ER 

PROVIDER: S-EPMC3983025 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Direct observation of differences of carotenoid polyene chain cis/trans isomers resulting from structural topology.

Schenk Emily R ER   Mendez Vanesa V   Landrum John T JT   Ridgeway Mark E ME   Park Melvin A MA   Fernandez-Lima Francisco F  

Analytical chemistry 20140128 4

In the present paper, trapped ion mobility spectrometry (TIMS) and theoretical calculations have been used to study carotenoid geometrical motifs generated by photoisomerization from the all-trans geometry. Multiple geometric isomers of the carotenoids lutein and zeaxanthin were separated using TIMS (R > 110) for [M](+), [M + H](+), and [M - 18](+) molecular species. Comparison of observed cross sections with those obtained from molecular dynamics calculations showed that the number of cis doubl  ...[more]

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