Enzymatic synthesis of D-sorbose and D-psicose with aldolase RhaD: effect of acceptor configuration on enzyme stereoselectivity

Bioorg Med Chem Lett. 2011 Dec 1;21(23):7081-4. doi: 10.1016/j.bmcl.2011.09.087. Epub 2011 Sep 29.

Abstract

It was previously reported that DHAP-dependent aldolase RhaD selectively chooses L-glyceraldehyde from racemic glyceraldehyde to produce l-fructose exclusively. Contrastingly, we discovered that D-glyceraldehyde is also tolerated as an acceptor and the stereoselectivity of the enzyme is lost in the corresponding aldol addition. Furthermore, we applied this property to efficiently synthesize two rare sugars D-sorbose and D-psicose.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehyde-Lyases / chemistry*
  • Chromatography, High Pressure Liquid
  • Fructose / chemical synthesis*
  • Fructose / chemistry
  • Glyceraldehyde / chemistry
  • Molecular Structure
  • Sorbose / chemical synthesis*
  • Sorbose / chemistry
  • Stereoisomerism

Substances

  • psicose
  • Fructose
  • Glyceraldehyde
  • Aldehyde-Lyases
  • rhamnulose-1-phosphate adolase
  • Sorbose