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