2',3'-Dideoxyadenosine 5'-triphosphate


CAS No. : 24027-80-3

2
Product Details
Cat No:R065553
Synonyms:ddATP
Molecular Formula:C10H16N5O11P3
Molecular Weight:475.183
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Cat No:R065553
Cas No:24027-80-3
Product-Name:2',3'-Dideoxyadenosine 5'-triphosphate
IUPAC Name:[[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
InChI:InChI=1S/C10H16N5O11P3/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(24-7)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h4-7H,1-3H2,(H,19,20)(H,21,22)(H2,11,12,13)(H2,16,17,18)/t6-,7+/m0/s1
InChIKey:OAKPWEUQDVLTCN-NKWVEPMBSA-N
SMILES:C1CC(OC1COP(=O)(O)OP(=O)(O)OP(=O)(O)O)N2C=NC3=C2N=CN=C3N
2/',3/'-Dideoxyadenosine 5/'-triphosphate (ddATP) is an in vitro inhibitor of reverse transcriptases from retroviruses, including HIV-1 and visna (Kis = 20 and 37 nM, respectively). It also blocks, in vitro, mammalian and bacterial DNA polymerases. ddATP, produced intracellularly by the phosphorylation of exogenously supplied 2’,3’-dideoxyadenosine, competes with dATP, resulting in chain termination. Because of this activity, dideoxynucleoside 5’-triphosphates, including ddATP, are used to terminate chain extension produced by the Taq polymerase used in polymerase chain reactions. It is also an antagonist of the purinergic receptor P2X2/3 (pIC50 = 6.5).
1.Boyle, N.A.,Rajwanshi, V.K.,Prhavc, M., et al. Synthesis of 2/',3/'-dideoxynucleoside 5/'-α-P-borano-β,γ-(difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcriptase. Journal of Medicinal Chemistry 48(7), 2695-2700 (2005).

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