Chiral detection of carotenoid assemblies

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Carotenoid assemblies were produced by aqueous dilution of ethanolic solutions. UV/VIS and CD spectroscopy revealed the formation of J- and H-types of aggregates of both right- and left-handed kinds. Simulation of UV/VIS spectra of the aggregates showed characteristic differences between the two types. 6′-Epimers of capsanthol ((all-E,3R,3′S,5′R)-β,κ-carotene- 3,3′,6′-triols) formed assemblies with increased chirality in dilute solution. While the absorption of 6′R-capsanthol giving H-type aggregate does not depend on the concentration, 6′S-capsanthol yielding J-type assembly showed concentration-dependent absorption intensity. Dilute aggregate of 6′R-capsanthol is characterized by an extremely large A value of -6,600. The transformation of J- to H-type assembly was observed in the mixtures of the epimers producing an intermediate kind of aggregate. A hypothetical structure for H-type assemblies is proposed.

Original languageEnglish
Pages (from-to)446-453
Number of pages8
JournalChirality
Volume13
Issue number8
DOIs
Publication statusPublished - Aug 20 2001

Keywords

  • Circular dichroism
  • Exciton signals
  • J to H transformation
  • Mixed aggregates
  • Supramolecular chirality

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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