Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis.
(R)-all-trans-3-hydroxyretinal 1, (S)-all-trans-4-hydroxyretinal and (R)-all-trans-4-hydroxyretinal have been synthesized stereoselectively by Horner-Wadsworth-Emmons and Stille cross-coupling as bond-forming reactions. The CBS method of ketone reduction was used in the enantioface-differentiation step to provide the precursors for the synthesis of the 4-hydroxyretinal enantiomers. The kinetic constants of Xenopus laevis ADH8 with these retinoids have been determined.
Domínguez
Marta
M
Departamento de Química Orgánica, Universidade de Vigo, 36310, Vigo, Spain.
Alvarez
Rosana
R
Borràs
Emma
E
Farrés
Jaume
J
Parés
Xavier
X
de Lera
Angel R
AR
D000426:Alcohol Dehydrogenase / Q000378:metabolism*; D004224:Diterpenes; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D012172:Retinaldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D029867:Xenopus Proteins
D004224:Diterpenes; D007659:Ketones; D029867:Xenopus Proteins; C057180:4-hydroxyretinal; C049427:3-hydroxyretinal; C475662:alcohol dehydrogenase 8; D000426:Alcohol Dehydrogenase; D012172:Retinaldehyde