6698-29-9Relevant academic research and scientific papers
Diadenosine 5',5'-(Boranated)polyphosphonate analogues as selective nucleotide pyrophosphatase/phosphodiesterase inhibitors ⊥
Eliahu, Shay,Lecka, Joanna,Reiser, Georg,Haas, Michael,Bigonnesse, Fran?ois,Lévesque, Sébastien A.,Pelletier, Julie,Sévigny, Jean,Fischer, Bilha
, p. 8485 - 8497 (2010)
Nucleotide pyrophosphatase/phosphodiesterases (NPPs) hydrolyze extracellular nucleotides and dinucleotides and thus control purinergic signaling. Enhanced NPP activity is implicated in health disorders such as osteoarthritis and cancer. We designed novel
Synthesis of bioconjugated sym -pentasubstituted corannulenes: Experimental and theoretical investigations of supramolecular architectures
Mattarella, Martin,Berstis, Laura,Baldridge, Kim K.,Siegel, Jay S.
, p. 115 - 128 (2014/02/14)
Applications of supramolecular architectures span a broad range of fields from medicinal chemistry to materials science and gas storage, making the design and synthesis of such structures a goal of high interest. The unique structural and symmetric proper
α,β-Difluoromethylene deoxynucleoside 5′-triphosphates: A convenient synthesis of useful probes for DNA polymerase β structure and function
Upton, Thomas G.,Kashemirov, Boris A.,McKenna, Charles E.,Goodman, Myron F.,Prakash, G. K. Surya,Kultyshev, Roman,Batra, Vinod K.,Shock, David D.,Pedersen, Lars C.,Beard, William A.,Wilson, Samuel H.
supporting information; experimental part, p. 1883 - 1886 (2009/10/10)
αβ-Difluoromethylene deoxynucleoside 5′-triphosphates (dNTPs, N = A or C) are advantageously obtained via phosphorylation of corresponding dNDP analogues using catalytic ATP, PEP, nucleoside diphosphate kinase, and pyruvate kinase. DNA pol β Kdd values for the α, β-CF2 and unmodified dNTPs, α, β-NH dUTP, and the α, β-CH2 analogues of dATP and dGTP are discussed in relation to the conformations of α, β-CF2 dTTP versus α, β-NH dUTP bound into the enzyme active site.2009 American Chemical Society.
α,β-Methylene-2′-deoxynucleoside 5′-triphosphates as noncleavable substrates for DNA polymerases: Isolation, characterization, and stability studies of novel 2′-deoxycyclonucleosides, 3,5′-cyclo-dG, and 2,5′-cyclo-dT
Liang, Fengting,Jain, Nidhi,Hutchens, Troy,Shock, David D.,Beard, William A.,Wilson, Samuel H.,Chiarelli, M. Paul,Cho, Bongsup P.
experimental part, p. 6460 - 6470 (2009/10/23)
We report synthesis and characterization of a complete set of α,β-methylene-2′-dNTPs (α,β-m-dNTP; N = A, C, T, G, 12-15) in which the α,β-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2′-deoxynucleoside 5′-diphosphate precursors, followed by an enzymatic γ-phosphorylation. All four synthesized α,β-m-dNTPs were found to be potent inhibitors of polymerase β, with Ki values ranging 1-5 μM. During preparation of the dG and dT derivatives of α,β-methylene diphosphate, we also isolated significant amounts of 3,5′-cyclo-dG (16) and 2,5′-cyclo-dT (17), respectively. These novel 2′-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 → C5′ and O2 → C5′, respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5′-cyclo-2′-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.
Novel P1,P2-substituted phosphonate analogues of 2'-deoxyadenosine and 2'-deoxythymidine 5'-triphosphates
Blackburn,Langston
, p. 6425 - 6428 (2007/10/02)
P1,P2-Substituted methylene, fluoromethylene, and difluoromethylene analogues of the deoxynucleotides 2'-deoxyadenosine 5'-triphosphate and thymidine 5'-triphosphate have been prepared by reaction between the bisphosphonic acid and t
Synthesis of Nucleotide 5'-Diphosphates from 5'-O-Tosyl Nucleosides
Davisson, V. Jo,Davis, Darrell R.,Dixit, Vyas M.,Poulter, C. Dale
, p. 1794 - 1801 (2007/10/02)
Procedures are described for the synthesis of nucleoside 5'-diphosphates, methanediphosphonates, and difluoromethanediphosphonates.The general strategy involves protection of the nucleosides as amidine, 2',3'-methoxymethylidene, and 3'-(tert-butyldimethylsilyl) derivatives prior to tosylation with tosyl chloride and (N,N-dimethylamino)pyridine.Deprotection, followed by displacement of the tosyl moiety with the tris(tetra-n-butylammonium) pyrophosphate, methanediphosphonate, or difluoromethanediphosphonate salts gave the desired products.The ammonium salts of the nucleotides were purified by flash chromatography on cellulose or medium pressure ion-exchange chromatography on DEAE Fractogel.Syntheses are reported for UDP (18), CDP (19), TDP (20), GDP (21), ADP (23), 2',3'-isopropylidene-ADP (22), adenosine 5'-methanediphosphonate (24), adenosine 5'-difluoromethanediphosphonate (25), and deoxyadenosine 5'-methanediphosphonate (27).In addition ATP (26) was prepared by treatment of 5'-O-tosyladenosine with tetrakis(tetra-n-butylammonium) thiophosphate.Yields for the displacement reactions ranged from 43percent to 93percent.
