Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis |
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Authors: | Domínguez Marta Alvarez Rosana Borràs Emma Farrés Jaume Parés Xavier de Lera Angel R |
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Affiliation: | Departamento de Química Orgánica, Universidade de Vigo, 36310, Vigo, Spain. |
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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. |
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