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

Org Biomol Chem. 2006 Jan 7;4(1):155-64. doi: 10.1039/b514273c. Epub 2005 Nov 30.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohol Dehydrogenase / metabolism*
  • Diterpenes
  • Hydrogenation
  • Ketones / chemistry
  • Kinetics
  • Retinaldehyde / analogs & derivatives*
  • Retinaldehyde / chemical synthesis*
  • Retinaldehyde / metabolism
  • Xenopus Proteins*

Substances

  • Diterpenes
  • Ketones
  • Xenopus Proteins
  • 4-hydroxyretinal
  • 3-hydroxyretinal
  • alcohol dehydrogenase 8
  • Alcohol Dehydrogenase
  • Retinaldehyde