An inhibitor of reverse transcriptases and DNA polymerases
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2',3'-Dideoxyadenosine 5'-triphosphate (lithium salt)

Item No. 17460

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2',3'-dideoxy-adenosine 5'-(tetrahydrogen triphosphate), lithium salt
Synonyms
  • ddATP
Molecular Formula
C10H16N5O11P3 • XLi
Formula Weight
475.2
Purity
≥98%
Formulation (Request formulation change)
A 10 mM solution in water
Solubility(Learn about Variance in Solubility)
Water: soluble
SMILES
O=P(OP(OP(O)(O)=O)(O)=O)(O)OC[C@@H]1CC[C@H](N2C=NC3=C2N=CN=C3N)O1.[Li]
InChi Code
InChI=1S/C10H16N5O11P3.Li/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
InChi Key
SKKDTNLQGHBADJ-UOERWJHTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µl

    $143

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    Product Description

    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).1,2,3 It also blocks, in vitro, mammalian and bacterial DNA polymerases.4,5 ddATP, produced intracellularly by the phosphorylation of exogenously supplied 2’,3’-dideoxyadenosine, competes with dATP, resulting in chain termination.4,5 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.6 It is also an antagonist of the purinergic receptor P2X2/3 (pIC50 = 6.5).7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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. J. Med. Chem. 48(7), 2695-2700 (2005).

    2. Frank, K.B., McKernan, P.A., Smith, R.A., et al. Visna virus as an in vitro model for human immunodeficiency virus and inhibition by ribavirin, phosphonoformate, and 2',3'-dideoxynucleosides. Antimicrob. Agents Chemother. 31(9), 1369-1374 (1987).

    3. Ueno, T., Shirasaka, T., and Mitsuya, H. Enzymatic characterization of human immunodeficiency virus type 1 reverse transcriptase resistant to multiple 2',3'-dideoxynucleoside 5'-triphosphates. The Journal of Biological Chemisty 270(40), 23605-23611 (1995).

    4. Toji, L., and Cohen, S.S. The enzymatic termination of polydeoxynucleotides by 2',3'-dideoxyadenosine triphosphate. Proc. Natl. Acad. Sci. USA 63(3), 871-877 (1969).

    5. Yagura, T., Kozu, T., and Seno, T. Mouse DNA polymerase accompanied by a novel RNA polymerase activity: Purification and partial characterization. J. Biochem. 91(2), 607-618 (1982).

    6. Li, Y., Mitaxov, V., and Waksman, G. Structure-based design of Taq DNA polymerases with improved properties of dideoxynucleotide incorporation. Proc. Natl. Acad. Sci. USA 96(17), 9491-9496 (1999).

    7. Jarvis, M.F., Bianchi, B., Uchic, J.T., et al. [3H]A-317491, a novel high-affinity non-nucleotide antagonist that specifically labels human P2X2/3 and P2X3 receptors. J. Pharmacol. Exp. Ther. 310(1), 407-416 (2004).