title: Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis.
abstract: (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.
authors.affiliation: Departamento de Química Orgánica, Universidade de Vigo, 36310, Vigo, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Domínguez
authors.forename: Rosana
authors.initials: R
authors.lastname: Alvarez
authors.forename: Emma
authors.initials: E
authors.lastname: Borràs
authors.forename: Jaume
authors.initials: J
authors.lastname: Farrés
authors.forename: Xavier
authors.initials: X
authors.lastname: Parés
authors.forename: Angel R
authors.initials: AR
authors.lastname: de Lera
mesh_terms: 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
chemical_list: D004224:Diterpenes; D007659:Ketones; D029867:Xenopus Proteins; C057180:4-hydroxyretinal; C049427:3-hydroxyretinal; C475662:alcohol dehydrogenase 8; D000426:Alcohol Dehydrogenase; D012172:Retinaldehyde