PMID: 2118802Jul 24, 1990Paper

(Difluoromethylene)phosphates of guanine nucleosides as probes of DNA polymerases and G proteins

Biochemistry
L ArabshahiG Wright

Abstract

5'-Polyphosphates of N2-(p-n-butylphenyl)-2'-deoxyguanosine and -guanosine which contain a difluoromethylene group in place of a phosphoanhydride oxygen have been synthesized. 5'-[beta,gamma-(Difluoromethylene)triphosphates], including that of 2'-deoxyguanosine, were prepared by reaction of the corresponding 5'-phosphates, activated by 1,1'-carbonyldiimidazole, with difluoromethanediphosphonate. The 5'-[(difluoromethylene)diphosphate] of N2-(p-n-butylphenyl)guanosine was prepared by treatment of a protected 5'-tosyl nucleoside with difluoromethanediphosphonate, followed by deprotection. Condensation of this nucleotide, activated with 1,1'-carbonyldiimidazole, with orthophosphate gave N2-(p-n-butylphenyl)guanosine 5'-[(alpha,beta-difluoromethylene)triphosphate]. Products were characterized by 31P and 19F NMR spectroscopy. The phosphonates were tested for their ability to displace [3H]GDP from the GTP binding proteins cellular (EC) and oncogenic (Leu-61) Ha-ras p21, and for their ability to inhibit DNA polymerase alpha from Chinese hamster ovary cells. The p21s bound weakly to a triphosphonate when the CF2 group was in the beta,gamma position, but not when it was in the alpha,beta position, and they did not bind to the correspond...Continue Reading

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Citations

Jan 1, 1990·Pharmacology & Therapeutics·G E Wright, N C Brown
Nov 23, 2007·Journal of the American Chemical Society·Charles E McKennaSamuel H Wilson
Jul 31, 2013·Medicinal Research Reviews·Ondřej Baszczyňski, Zlatko Janeba
Dec 24, 2004·Journal of Medicinal Chemistry·Guangyi WangP Dan Cook
Sep 14, 2006·Chemical Reviews·Vadim D Romanenko, Valery P Kukhar
Dec 6, 2005·The Journal of Organic Chemistry·Samy Mohamady, David L Jakeman

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