title: Optical resolution of (+/-)-all-trans-3-hydroxyretinal by use of high-performance liquid chromatography.
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).
authors.affiliation: Kobe Women's College of Pharmacy, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Ito
authors.forename: Y
authors.initials: Y
authors.lastname: Katsuta
authors.forename: M
authors.initials: M
authors.lastname: Koyama
authors.forename: M
authors.initials: M
authors.lastname: Murakami
authors.forename: N
authors.initials: N
authors.lastname: Iwaki
authors.forename: A
authors.initials: A
authors.lastname: Okano
authors.forename: K
authors.initials: K
authors.lastname: Tsukida
mesh_terms: D002851:Chromatography, High Pressure Liquid; D012172:Retinaldehyde / Q000031:analogs & derivatives* / Q000032:analysis
chemical_list: C049427:3-hydroxyretinal; D012172:Retinaldehyde