Chemical and enzymatic methodologies for the synthesis of enantiomerically pure glyceraldehyde 3-phosphates

Carbohydr Res. 2014 May 7;389:18-24. doi: 10.1016/j.carres.2013.12.023. Epub 2014 Jan 10.

Abstract

Glyceraldehyde 3-phosphates are important intermediates of many central metabolic pathways in a large number of living organisms. d-Glyceraldehyde 3-phosphate (d-GAP) is a key intermediate during glycolysis and can as well be found in a variety of other metabolic pathways. The opposite enantiomer, l-glyceraldehyde 3-phosphate (l-GAP), has been found in a few exciting new pathways. Here, improved syntheses of enantiomerically pure glyceraldehyde 3-phosphates are reported. While d-GAP was synthesized by periodate cleavage of d-fructose 6-phosphate, l-GAP was obtained by enzymatic phosphorylation of l-glyceraldehyde. (1)H- and (31)P NMR spectroscopy was applied in order to examine pH-dependent behavior of GAP over time and to identify potential degradation products. It was found that GAP is stable in acidic aqueous solution below pH 4. At pH 7, methylglyoxal is formed, whereas under alkaline conditions, the formation of lactic acid could be observed.

Keywords: Enzymatic phosphorylation; Glycerokinase; Glycolysis; d-Glyceraldehyde 3-phosphate; l-Glyceraldehyde 3-phosphate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cellulomonas / enzymology
  • Chemistry Techniques, Synthetic
  • Drug Stability
  • Glyceraldehyde 3-Phosphate / chemical synthesis*
  • Glyceraldehyde 3-Phosphate / chemistry*
  • Glycerol Kinase / metabolism*
  • Hydrogen-Ion Concentration
  • Stereoisomerism

Substances

  • Glyceraldehyde 3-Phosphate
  • Glycerol Kinase