Synthesis of 11-cis-locked bicyclo[5.1.0]octanyl retinal and an enantioselective binding to bovine opsin

Yukari Fujimoto, Rongyuan Xie, Sarah E. Tully, Nina Berova, Koji Nakanishi

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8 Citations (Scopus)

Abstract

Both enantiomers of 13-(E) and 13-(Z) isomers of 11-cis-locked bicyclo[5.1.0]octanyl retinal were prepared by an improved synthesis and incubated with bovine opsin. The synthesis also establishes the absolute configuration of the enantiomers. Only one of the enantiomers binds to opsin, thus showing the steric restrictions regarding the middle polyene moiety of the retinoid molecule; this is in sharp contrast to the known leniency of the ring moiety binding site of retinoids. However, although one enantiomer is incorporated into the pigment, the circular dichroic spectrum of the pigment incorporating the bound enantiomer yields only a very weak Cotton effect, showing that, once incorporated, the bicyclo[5.1.0]octanyl chromophore is flattened by the opsin binding site. The titled retinoid was synthesized for study of the absolute conformation of the retinal pigment in rhodopsin.

Original languageEnglish
Pages (from-to)340-346
Number of pages7
JournalChirality
Volume14
Issue number4
DOIs
Publication statusPublished - 2002 Apr 27
Externally publishedYes

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Keywords

  • Chiral discrimination
  • Chiral separation
  • Circular dichroic spectroscopy (CD)
  • Cyclopropyl retinoid
  • Exciton coupled CD
  • Rhodopsin

ASJC Scopus subject areas

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

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