A reverse transcriptase inhibitor
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2',3'-Dideoxythymidine-5'-O-triphosphate (sodium salt)

Item No. 38376

Technical Information
Formal Name
((2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl triphosphate
Synonyms
  • ddTTP
Molecular Formula
C10H13N2O13P3 • 4Na
Formula Weight
Purity
≥95%
A 10 mM solution in water
Water: Soluble
SMILES
O=C(N(C=C1C)[C@H]2CC[C@@H](COP([O-])(OP(OP([O-])([O-])=O)([O-])=O)=O)O2)NC1=O.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C10H17N2O13P3.4Na/c1-6-4-12(10(14)11-9(6)13)8-3-2-7(23-8)5-22-27(18,19)25-28(20,21)24-26(15,16)17;;;;/h4,7-8H,2-3,5H2,1H3,(H,18,19)(H,20,21)(H,11,13,14)(H2,15,16,17);;;;/q;4*+1/p-4/t7-,8+;;;;/m0..../s1
InChi Key
OKYHUQUPPJASGU-JWQBCWJNSA-J
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    Product Description

    2',3'-Dideoxythymidine-5'-O-triphosphate (ddTTP) is a reverse transcriptase inhibitor (Kis = 40 and 25 nM for the visna virus and HIV-1 enzymes, respectively).1,2 It also inhibits DNA polymerase γ (Ki = 400 nM for the bovine enzyme).3 ddTTP has been used to terminate chain extension produced by the Taq polymerase in PCR assays.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Frank, K.B., McKernan, P.A., Smith, R.A., et alVisna 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).

    2. 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).

    3. Izuta, S., Saneyoshi, T., Sakurai, T., et alThe 5′-triphosphates of 3′-azido-3′-deoxythymidine and 2′, 3′-dideoxynucleosides inhibit DNA polymerase γ by different mechanisms. Biochm. Biophys. Res. Commun. 179(2), 776-783 (1991).

    4. 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).