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Issue 1, 2006
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Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis

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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.

Graphical abstract: Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis

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Publication details

The article was received on 10 Oct 2005, accepted on 08 Nov 2005 and first published on 30 Nov 2005


Article type: Paper
DOI: 10.1039/B514273C
Citation: Org. Biomol. Chem., 2006,4, 155-164
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    Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis

    M. Domínguez, R. Álvarez, E. Borràs, J. Farrés, X. Parés and A. R. de Lera, Org. Biomol. Chem., 2006, 4, 155
    DOI: 10.1039/B514273C

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