A reverse transcriptase inhibitor and an active metabolite of ddA and ddI
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2',3'-Dideoxyadenosine-5'-O-triphosphate (sodium salt)

Item No. 38373

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2′,3′-dideoxy-adenosine 5′-(tetrahydrogen triphosphate), tetrasodium salt
CAS Number
99827-72-2
Synonyms
  • ddATP
  • Dideoxyadenosine-5'-triphosphate
Molecular Formula
C10H12N5O11P3 • 4Na
Formula Weight
563.1
Purity
≥95%
Formulation (Request formulation change)
A 10 mM solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
NC1=C(N=C2)C(N2[C@H]3CC[C@@H](COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)O3)=NC=N1.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C10H16N5O11P3.4Na/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);;;;/q;4*+1/p-4/t6-,7+;;;;/m0..../s1
InChi Key
HIQMRNGZTRSRFK-NOTWHITJSA-J
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2.4 mg

    $224

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    Product Description

    2',3'-Dideoxyadenosine-5'-O-triphosphate is a reverse transcriptase inhibitor (Kis = 20 and 37 nM for the HIV and visna virus enzymes, respectively) and an active metabolite of 2′,3′-dideoxyadenosine (ddA; Item No. 36662) and didanosine (ddI; Item No. 23715).1,2,3 It is formed from ddI via a 2',3'-dideoxyAMP intermediate by phosphoribosyl pyrophosphate synthase (PRS).3 It inhibits DNA polymerase isolated from mouse Ehrlich ascites tumor cells in the presence of ATP or GDP (Kis = 60 and 18 µM, respectively).4 2',3'-Dideoxyadenosine-5'-O-triphosphate and other dideoxynucleoside 5'-triphosphates are commonly used to terminate chain extension by Taq polymerases in PCR assays.5

    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. Kewn, S., Hoggard, P.G., Henry-Mowatt, J.S., et al. Intracellular activation of 2',3'-dideoxyinosine and drug interactions in vitro. AIDS Res. Hum. Restroviruses 15(9), 793-802 (1999).

    4. 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).

    5. 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).