Phosphonomethyl analogues of hexose phosphates.
The analogue of fructose 1,6-bisphosphate in which the phosphate group, -O-PO3H2, on C-6 is replaced by the phosphonomethyl group, -CH2-PO3H2, was made enzymically from the corresponding analogue of 3-phosphoglycerate. It was a substrate for aldolase, which was used to form it, but not for fructose 1,6-bisphosphatase. It was hydrolysed chemically to yield the corresponding analogue of fructose 6-phosphate [i.e. 6-deoxy-6-(phosphonomethyl)-D-fructose, or, more strictly, 6,7-dideoxy-7-phosphono-D-arabino-2-heptulose]. This proved to be a substrate for the sequential actions of glucose 6-phosphate isomerase, glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase. Thus seven out of the nine enzymes of the glycolytic and pentose phosphate pathways so far tested catalyse the reactions of the phosphonomethyl isosteres of their substrates.
D006597:Fructose-Bisphosphatase / Q000037:antagonists & inhibitors / Q000378:metabolism; D005634:Fructose-Bisphosphate Aldolase / Q000378:metabolism; D006600:Hexosephosphates / Q000096:biosynthesis* / Q000494:pharmacology; D006601:Hexoses / Q000032:analysis; D006885:Hydroxybutyrates / Q000378:metabolism; D009243:NAD / Q000378:metabolism; D009249:NADP / Q000378:metabolism; D063065:Organophosphonates / Q000096:biosynthesis* / Q000494:pharmacology; D010728:Phosphoenolpyruvate / Q000378:metabolism
D006600:Hexosephosphates; D006601:Hexoses; D006885:Hydroxybutyrates; D063065:Organophosphonates; D009243:NAD; D009249:NADP; D010728:Phosphoenolpyruvate; D006597:Fructose-Bisphosphatase; D005634:Fructose-Bisphosphate Aldolase