Efficient enzymatic synthesis of L-rhamnulose and L-fuculose

Bioorg Med Chem Lett. 2016 Feb 1;26(3):969-972. doi: 10.1016/j.bmcl.2015.12.051. Epub 2015 Dec 17.

Abstract

L-Rhamnulose (6-deoxy-L-arabino-2-hexulose) and L-fuculose (6-deoxy-L-lyxo-2-hexulose) were prepared from L-rhamnose and L-fucose by a two-step strategy. In the first reaction step, isomerization of L-rhamnose to L-rhamnulose, or L-fucose to L-fuculose was combined with a targeted phosphorylation reaction catalyzed by L-rhamnulose kinase (RhaB). The by-products (ATP and ADP) were selectively removed by silver nitrate precipitation method. In the second step, the phosphate group was hydrolyzed to produce L-rhamnulose or L-fuculose with purity exceeding 99% in more than 80% yield (gram scale).

Keywords: De-phosphorylation; Enzymatic synthesis; Phosphorylation; l-Fuculose; l-Rhamnulose.

Publication types

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

MeSH terms

  • Biocatalysis
  • Chemical Precipitation
  • Chromatography, High Pressure Liquid
  • Fucose / metabolism
  • Hexoses / biosynthesis*
  • Hexoses / chemistry
  • Hexoses / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Phosphotransferases (Alcohol Group Acceptor) / metabolism
  • Rhamnose / analogs & derivatives*
  • Rhamnose / biosynthesis*
  • Rhamnose / chemistry
  • Rhamnose / isolation & purification
  • Rhamnose / metabolism
  • Silver Nitrate / chemistry

Substances

  • Hexoses
  • fuculose
  • Fucose
  • Silver Nitrate
  • Phosphotransferases (Alcohol Group Acceptor)
  • rhamnulokinase
  • Rhamnose