Is (9Z)-"meso"-zeaxanthin optically active?

Chirality. 2001 May 5;13(4):224-9. doi: 10.1002/chir.1023.

Abstract

The question raised in the title was answered. (3R, 3'S)-meso-Zeaxanthin was submitted to iodine catalyzed photochemical stereoisomerisation. The enantiomeric (9Z) and (9'Z) geometrical isomers were isolated by semipreparative HPLC and separated as diastereomeric dicarbamates on a chiral column only. Cleavage of the carbamate could not be effected. CD-Spectra of (1"S, 1"S)- and (1"R, 1"R)-dicarbamates of geometrical isomers of (3R, 3'R)- and (3R, 3'S)-meso-zeaxanthin were systematically studied and the contribution from the carbamate moieties revealed. It was concluded that (9Z, 3R, 3'S)-"meso"-zeaxanthin, in spite of having no symmetry elements, is optically inactive. The result has been rationalised in line with the current hypothesis on the origin of carotenoid CD spectra.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Stereoisomerism
  • Xanthophylls
  • Zeaxanthins
  • beta Carotene / analogs & derivatives
  • beta Carotene / chemistry*
  • beta Carotene / isolation & purification

Substances

  • Xanthophylls
  • Zeaxanthins
  • beta Carotene
  • meso-zeaxanthin