Issue 1, 2006
From the journal:

Organic & Biomolecular Chemistry

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

Marta Domínguez,a   Rosana Álvarez,a   Emma Borràs,b   Jaume Farrés,b   Xavier Parésb  and  Angel R. de Lera*a  

* Corresponding authors

a Departamento de Química Orgánica, Universidade de Vigo, Vigo, Spain
E-mail: qolera@uvigo.es
Fax: +34-986-811940
Tel: +34-986-812316

b Department of Biochemistry and Molecular Biology, Universitat Autònoma de Barcelona, E-08193 Bellaterra, Barcelona, Spain

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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Article information

DOI
https://doi.org/10.1039/B514273C
Article type
Paper
Submitted
10 Oct 2005
Accepted
08 Nov 2005
First published
30 Nov 2005

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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