(3-formyl-but-3-enyl)-phosphonic acid

(3-formyl-but-3-enyl)-phosphonic acid is a synthetic small molecule belonging to the class of organic phosphonic acids. Its molecular formula is C5H9O4P and it features an α,β-unsaturated aldehyde moiety attached to a phosphonic acid group[1][2][5]. The compound has been studied primarily as an experimental inhibitor and structural probe in enzymology research. Notably, it acts as an irreversible inhibitor of glyceraldehyde-3-phosphate dehydrogenase (GAPDH), forming a covalent thioacyl enzyme intermediate that mimics the catalytic intermediate state[8][9]. This property makes it valuable for mechanistic studies of GAPDH and related enzymes but there are no known therapeutic indications or clinical uses.

Other names

(3-formylbut-3-en-1-yl)phosphonic acid(3-methylidene-4-oxobutyl)phosphonic acid3-formylbut-3-enylphosphonic acid3-methanoylbut-3-enylphosphonic acid