A four-step enzymatic cascade for the one-pot synthesis of non-natural carbohydrates from glycerol

J Org Chem. 2000 Oct 20;65(21):6940-3. doi: 10.1021/jo000492y.

Abstract

A total of four enzymatic steps were combined, in a one-pot reaction, to synthesize carbohydrates starting from glycerol. First, phosphorylation of glycerol by reaction with pyrophosphate in the presence of phytase at pH 4.0 in 95% glycerol afforded racemic glycerol-3-phosphate in 100% yield. The L-enantiomer of the latter underwent selective aerobic oxidation to dihydroxyacetone phosphate (DHAP) at pH 7.5 in the presence of glycerolphosphate oxidase (GPO) and catalase. Subsequently, fructose-1,6-bisphosphate aldolase catalyzed the aldol reaction of DHAP with butanal. Finally, dephosphorylation of the aldol adduct was mediated by phytase at pH 4 affording 5-deoxy-5-ethyl-D-xylulose in 57% yield from L-glycerol-3-phosphate. The phytase on/off-switch by pH was the key to controlling phosphorylation and dephosphorylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemical synthesis*
  • Catalysis
  • Diphosphates / chemistry
  • Enzymes
  • Glycerol / chemistry*
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Oxidation-Reduction
  • Phosphorylation
  • Spectrophotometry, Ultraviolet

Substances

  • Carbohydrates
  • Diphosphates
  • Enzymes
  • Glycerol