2',3'-Dideoxyadenosine 5'-triphosphate

• CAT Number: R065553
• CAS Number: 24027-80-3
• Molecular Formula: C10H16N5O11P3
• Molecular Weight: 475.18
• 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: C1C[C@@H](O[C@@H]1COP(=O)(O)OP(=O)(O)OP(=O)(O)O)N2C=NC3=C(N=CN=C32)N

2′,3′-Dideoxyadenosine 5′-triphosphate (Cat No.:R065553) is a nucleotide analog used in molecular biology, particularly in DNA sequencing and as an antiviral agent. It is a modified form of adenine with the 3′-hydroxyl group removed, which prevents the addition of subsequent nucleotides during DNA chain elongation. This property makes ddATP a chain terminator in the Sanger sequencing method, where it is incorporated into growing DNA strands, halting their extension. ddATP is also investigated as an antiviral agent, especially in the treatment of HIV, by inhibiting viral DNA synthesis through its incorporation into the viral genome.

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).