2',3'-Dideoxyadenosine 5'-triphosphate

• CAT Number: R065553
• CAS Number: 24027-80-3
• Molecular Formula: C10H16N5O11P3
• Molecular Weight: 475.183
• Purity: ≥95%
• Synonyms: ddATP
• Storage: -20°C
• 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,CAS 24027-80-3) 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).

Reference

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).