| Identification | Back Directory | [Name]
Adenosine 5′-(tetrahydrogen triphosphate), 2′,3′-dideoxy-, tetrasodium salt | [CAS]
99827-72-2 | [Synonyms]
2',3'-Dideoxyadenosine-5'-O-triphosphate (sodium salt)
Adenosine 5′-(tetrahydrogen triphosphate), 2′,3′-dideoxy-, tetrasodium salt | [Molecular Formula]
C10H16N5O11P3.4Na | [Molecular Weight]
567.14 |
| Hazard Information | Back Directory | [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.5WARNING This product is not for human or veterinary use. | [References]
[1] NICHOLAS A. BOYLE. Synthesis of 2‘,3‘-Dideoxynucleoside 5‘-α-P-Borano-β,γ-(difluoromethylene)triphosphates and Their Inhibition of HIV-1 Reverse Transcriptase[J]. Journal of Medicinal Chemistry, 2005, 48 7: 2695-2700. DOI: 10.1021/jm040101y
[2] K B FRANK. Visna virus as an in vitro model for human immunodeficiency virus and inhibition by ribavirin, phosphonoformate, and 2’,3’-dideoxynucleosides.[J]. Antimicrobial Agents and Chemotherapy, 1987, 31 9: 1369-1374. DOI: 10.1128/aac.31.9.1369
[3] S KEWN. Intracellular activation of 2’,3’-dideoxyinosine and drug interactions in vitro.[J]. AIDS research and human retroviruses, 1999, 15 9: 793-802. DOI: 10.1089/088922299310692
[4] T YAGURA T S T Kozu. Mouse DNA polymerase accompanied by a novel RNA polymerase activity: purification and partial characterization.[J]. Journal of biochemistry, 1982, 91 2: 607-618. DOI: 10.1093/oxfordjournals.jbchem.a133732
[5] Y LI G W V Mitaxov. Structure-based design of Taq DNA polymerases with improved properties of dideoxynucleotide incorporation.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1999, 96 17: 9491-9496. DOI: 10.1073/pnas.96.17.9491 |
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