Paper
9-(DIFLUOROPHOSPHONOALKYL)GUANINES AS A NEW CLASS OF MULTISUBSTRATE ANALOGUE INHIBITORS OF PURINE NUCLEOSIDE PHOSPHORYLASE
Published 1991 · S. Halazy, A. Ehrhard, C. Danzin
Journal of the American Chemical Society
98
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1
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Abstract
9-(5,5-Difluoro-5-phosphonopentyl) guanine (3) was synthesized as a potential multisubstrate analogue inhibitor of purine nucleoside phosphorylase (EC 2.4.2.1. PNP). At pH 7.4, 3 has a K i value 18-, 26-, 25-, and 5.5-fold lower than that of the nonfluorinated analogue 9-(5-phosphonopentyl) guanine (2) regarding PNP from human erythrocyte, rat erythrocyte, calf spleen, and Escherichia coli, respectively. The superiority of the difluorophosphonate 3 over the phosphonate 2 is explained by electronic as well as by steric effects
Highly Cited9-(5,5-DIFLUOROPHOSPHONOALKYL)GUANINES ARE A SUBTLE MULTISUBSTRATE ANALOGUE INHIBITORS OF PURINE NUCLEOSIDE PHOSPHORYLASE, OUTSTANDING ITS NON
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