Synthesis of enantiopure C<inf>3</inf>- and C<inf>4</inf>-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis

Marta Domínguez, Rosana Álvarez, Emma Borràs, Jaume Farrés, Xavier Parés, Angel R. De Lera

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10 Citations (Scopus)

Abstract

(R)-all-trans-3-hydroxyretinal 1, (S)-all-trans-4-hydroxyretinal 3 and (R)-all-trans-4-hydroxyretinal 5 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. © The Royal Society of Chemistry 2006.
Original languageEnglish
Pages (from-to)155-164
JournalOrganic and Biomolecular Chemistry
Volume4
DOIs
Publication statusPublished - 14 Apr 2006

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