title: Chemical and enzymatic methodologies for the synthesis of enantiomerically pure glyceraldehyde 3-phosphates.
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.
authors.affiliation: Sigma-Aldrich GmbH, Industriestrasse 25, 9471 Buchs, Switzerland.
authors.forename: Dominik
authors.initials: D
authors.lastname: Gauss
authors.affiliation: Sigma-Aldrich GmbH, Industriestrasse 25, 9471 Buchs, Switzerland.
authors.forename: Bernhard
authors.initials: B
authors.lastname: Schoenenberger
authors.affiliation: Sigma-Aldrich GmbH, Industriestrasse 25, 9471 Buchs, Switzerland. Electronic address: roland.wohlgemuth@sial.com.
authors.forename: Roland
authors.initials: R
authors.lastname: Wohlgemuth
mesh_terms: D040143:Cellulomonas / Q000201:enzymology; D060326:Chemistry Techniques, Synthetic; D004355:Drug Stability; D005986:Glyceraldehyde 3-Phosphate / Q000138:chemical synthesis* / Q000737:chemistry*; D005991:Glycerol Kinase / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism
chemical_list: D005986:Glyceraldehyde 3-Phosphate; D005991:Glycerol Kinase
keywords: Enzymatic phosphorylation; Glycerokinase; Glycolysis; d-Glyceraldehyde 3-phosphate; l-Glyceraldehyde 3-phosphate