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  • Title: Optical resolution of (+/-)-all-trans-3-hydroxyretinal by use of high-performance liquid chromatography.
    Author: Ito M, Katsuta Y, Koyama M, Murakami M, Iwaki N, Okano A, Tsukida K.
    Journal: J Nutr Sci Vitaminol (Tokyo); 1992 Apr; 38(2):111-5. PubMed ID: 1506917.
    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).
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