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- W87105160 abstract "A carotenoid with a β-end-ring is an intrinsically chiral chromophore by virtue of the twist about the formal single bond connecting the planar conjugated chain with the end-ring. Steric hindrance prevents the double bond in the ring from lying coplanar with the chain. Fixation of the conformation of the ring itself by an equatorial substituent at C(2) and/or C(3) gives preference to one handedness of the twist of the ring against the chain resulting in an intrinsically chiral conjugated chain. With this model many features of the c.d. spectra of carotenoids can be understood. Three rules have been given to describe the experimental observations 4 . 1. All- trans and di- cis isomers have very similar c.d. spectra, which are approximately mirror-images of those of the mono- cis isomers of the same carotenoid. 2. The c.d. spectra of carotenoids with only one end-ring do not invert on cis -isomerization. 3. The c.d. spectra are temperature-dependent. These rules are shown to hold for a number of trans , mono- and di- cis astaxanthin diacetates. The limitations and possible extensions of these rules are explored with other carotenoids, including those with epoxy rings and ɛ-rings, such as lutein isomers and epimers and chiriquixanthin epimers and related compounds. The conformational flexibility has implications for the use of the c.d. spectra in the determination of the absolute stereochemistry. The c.d. spectra of 9-mono- cis and 9,9′-di- cis astaxanthin diacetates at −180°C are strongly concentration-dependent, which suggests anassociation of these compounds at low temperature in solution." @default.
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- W87105160 date "1982-01-01" @default.
- W87105160 modified "2023-09-25" @default.
- W87105160 title "CIRCULAR DICHROISM OF CAROTENOIDS AND ITS USE IN INVESTIGATIONS OF THEIR STRUCTURES, CONFIGURATIONS AND CONFORMATIONS" @default.
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- W87105160 doi "https://doi.org/10.1016/b978-0-08-026224-6.50013-9" @default.
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