A two-step strategy for the preparation of 6-deoxy-l-sorbose

Bioorg Med Chem Lett. 2016 Sep 1;26(17):4358-61. doi: 10.1016/j.bmcl.2016.03.083. Epub 2016 Mar 25.

Abstract

A two-step enzymatic strategy for the efficient and convenient synthesis of 6-deoxy-l-sorbose was reported herein. In the first reaction step, the isomerization of l-fucose (6-deoxy-l-galactose) to l-fuculose (6-deoxy-l-tagatose) catalyzed by l-fucose isomerase (FucI), and the epimerization of l-fuculose to 6-deoxy-l-sorbose catalyzed by d-tagatose 3-epimerase (DTE) were coupled with the targeted phosphorylation of 6-deoxy-l-sorbose by fructose kinase from human (HK) in a one-pot reaction. The resultant 6-deoxy-l-sorbose 1-phosphate was purified by silver nitrate precipitation method. In the second reaction step, the phosphate group of the 6-deoxy-l-sorbose 1-phosphate was hydrolyzed with acid phosphatase (AphA) to produce 6-deoxy-l-sorbose in 81% yield with regard to l-fucose.

Keywords: 6-Deoxy-l-sorbose; Dephosphorylation; Enzymatic synthesis; One-pot multienzyme; Phosphorylation.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Chromatography, High Pressure Liquid
  • Humans
  • Isomerism
  • Sorbose / analogs & derivatives*
  • Sorbose / chemical synthesis*
  • Sorbose / chemistry

Substances

  • Sorbose