Optical resolution of (+/-)-all-trans-3-hydroxyretinal by use of high-performance liquid chromatography

J Nutr Sci Vitaminol (Tokyo). 1992 Apr;38(2):111-5. doi: 10.3177/jnsv.38.111.

Abstract

Racemic all-trans-3-hydroxyretinal (3-OH-RAL) (1) was converted by a reaction with (-)-camphanic acid chloride (CpCl) into a diastereomixture of camphanates (2a) and (2b) which was separated by preparative high-performance liquid chromatography (HPLC) to give two esters (2a) and (2b) in pure state, respectively. Saponification of (2a) and (2b) independently afforded optically active (3S)- and (3R)-3-OH-RALs (3a) and (3b), respectively, whose absolute structures were determined by circular dichroism (CD) spectra. Racemic 3-OH-RAL was separated to two peaks by HPLC using chiral column (ChiraSpher, Merck). Cochromatography with authentic specimens (3a) and (3b) showed that the peak with a short retention time corresponded to (3R)-isomer and the other to (3S).

MeSH terms

  • Chromatography, High Pressure Liquid
  • Retinaldehyde / analogs & derivatives*
  • Retinaldehyde / analysis

Substances

  • 3-hydroxyretinal
  • Retinaldehyde