M. O'Leary, W. J. Degooyer, T. M. Dougherty
Jun 16, 1981
Citations
0
Influential Citations
15
Citations
Journal
Biochemical and biophysical research communications
Abstract
Abstract 1-Hydroxycyclopropane carboxylic acid phosphate has been synthesized from diethyl succinate by acyloin condensation followed by ring contraction and phosphorylation. This compound is a potent competitive inhibitor of enzymes utilizing phosphoenolpyruvate. For phosphoenolpyruvate from maize, Ki = 7.3 μM at pH 8.0 in the presence of Mg2+. For pyruvate kinase, Ki = 2.0 mM at pH 7.0. For enolase, Ki = 8.0 μM at pH 8.0. In each case, this compound is a substantially better inhibitor than the commonly used phosphoenolpyruvate analogs phosphoglycolate and phospholactate, presumably because of the similarity in geometric and electronic structure between the cyclopropane compound and phosphoenolpyruvate.