Synthesis of the P1, P2-methylene analog of N2-(p-n-butylphenyl)-2'- deoxyguanosine 5'-triphosphate: A non-substrate inhibitor of DNA polymerases

Article abstract of DOI:10.1080/15257779408013245

N²-(p-n-Butylphenyl)-2'-deoxyguanosine 5'-(P¹, P²-methylene)- triphosphate (BuPdGMPCH₂PP) has been synthesized. Displacement of the mesyloxy group of 5'-MesBuPdG by methanediphosphonate gave 30% of BuPdGMPCH₂P, but 68% of 3,5'-cycloBuPdG. Reaction of the nucleoside BuPdG with methanediphosphonate and DCC gave 62% of BuPdGMPCH₂PPCH₂P, which was hydrolyzed to BuPdGMPCH₂P in 77% yield. The title compound was obtained by reacting the imidazolide of BuPdGMPCH₂P with orthophosphate. BuPdGMPCH₂PP inhibited calf thymus DNA polymerase α with K(i) = 9.5 nM, a potency only fivefold weaker than that of BuPdGTP itself.

Full text of DOI:10.1080/15257779408013245

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Synthesis of the P1, P2-Methylene
Analog of N2- (p-n-Butylphenyl)-2′-
deoxyguanosine 5′-Triphosphate: A Non-
substrate Inhibitor of DNA Polymerases
Ivan Yanachkov a & George E. Wright a
a Department of Pharmacology , University of Massachusetts Medical
School , Worcester, MA, 01655
Published online: 23 Sep 2006.
To cite this article: Ivan Yanachkov & George E. Wright (1994) Synthesis of the P1, P2-Methylene
Analog of N2- (p-n-Butylphenyl)-2′- deoxyguanosine 5′-Triphosphate: A Non-substrate Inhibitor of DNA
Polymerases, Nucleosides and Nucleotides, 13:1-3, 339-350, DOI: 10.1080/15257779408013245
To link to this article: http://dx.doi.org/10.1080/15257779408013245
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