Phosphonomethyl analogues of phosphate ester glycolytic intermediates.
Analogues of dihydroxyacetone phosphate and of 3-phosphoglycerate were made in which the phosphate group, -O-PO(3)H(2), is replaced by the phosphonomethyl group, -CH(2)-PO(3)H(2). The analogue of dihydroxyacetone phosphate is a substrate for aldolase and glycerol 1-phosphate dehydrogenase (Stribling, 1974), but not for triose phosphate isomerase. The analogue of 3-phosphoglycerate oxidizes NADH under the combined action of 3-phosphoglycerate kinase and glyceraldehyde 3-phosphate dehydrogenase if ATP is added. Thus four out of the five glycolytic enzymes tested handle the phosphonomethyl compounds like the natural phosphates.
D000255:Adenosine Triphosphate; D004952:Esters; D005634:Fructose-Bisphosphate Aldolase; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; D005993:Glycerolphosphate Dehydrogenase; D006019:Glycolysis; D009243:NAD; D063065:Organophosphonates / Q000138:chemical synthesis*; D010710:Phosphates; D010735:Phosphoglycerate Kinase; D014306:Trioses
D004952:Esters; D063065:Organophosphonates; D010710:Phosphates; D014306:Trioses; D009243:NAD; D000255:Adenosine Triphosphate; D005993:Glycerolphosphate Dehydrogenase; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; D010735:Phosphoglycerate Kinase; D005634:Fructose-Bisphosphate Aldolase