365-08-2

Basic information

• Product Name: thymidine 5'-(tetrahydrogen triphosphate)
• Synonyms: thymidine 5'-(tetrahydrogen triphosphate);[hydroxy-[hydroxy-[[3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-oxolan-2-yl]methoxy]phosphoryl]oxy-phosphoryl]oxyphosphonic acid;Thymidine-5''-triphosphoric acid;2'-Deoxythymidine triposphate;5-Methyl-dUTP;5'-TTP;Deoxy-TTP
• CAS NO: 365-08-2
• Molecular Formula: C₁₀H₁₇N₂O₁₄P₃
• Molecular Weight: 482.168263
• EINECS: 206-669-7
• Mol File: 365-08-2.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• Density: 1.922 g/cm³
• Storage Temp.: 2-8°C
• PKA: 0.80±0.50(Predicted)
• CAS DataBase Reference: thymidine 5'-(tetrahydrogen triphosphate)(CAS DataBase Reference)
• NIST Chemistry Reference: thymidine 5'-(tetrahydrogen triphosphate)(365-08-2)
• EPA Substance Registry System: thymidine 5'-(tetrahydrogen triphosphate)(365-08-2)

Safety Data

• Hazardous Substances Data: 365-08-2(Hazardous Substances Data)

Usage

General Description

Thymidine 5'-(tetrahydrogen triphosphate) is a nucleoside triphosphate molecule that consists of thymidine and three phosphate groups. It is an essential building block for DNA synthesis and repair, as it provides the necessary energy and phosphate groups for the formation of new DNA strands. Thymidine triphosphate is involved in the replication of genetic material and plays a crucial role in the maintenance and transmission of genetic information. It is also a key component in the production of nucleic acids, which are vital for the functioning of all living cells. Thymidine 5'-(tetrahydrogen triphosphate) is utilized by enzymes such as DNA polymerases and helicases during DNA replication and repair processes.

Upstream product

• 50-89-5 thymidine 
• 208115-15-5 2-(3'-O-acetyl-2'-deoxythymidin-5'-yl)-4H-1,3,2-benzodioxaphosphorin-4-one 
• 21090-30-2 3'-O-acetylthymidine 
• 101527-40-6 5'-O-tert-butyldiphenylsilylthymidine 

Downstream Products

• 515138-64-4 C₁₆H₂₅N₅O₁₅P₂ 
• 7132-58-3 dTDP-4-keto-6-deoxy-D-glucose 
• 2147-59-3 thymidine 5'-diphospho-β-L-rhamnose 
• 86119-84-8 phosphoric acid 
• 16752-71-9 thymidine diphosphate 4-keto-6-deoxy-α-D-glucose 
• 515138-66-6 3-O-methyl-dTDP-α-D-glucose 
• 38168-82-0 glyceric acid 1,3-biphosphate 
• 62012-79-7 dTDP-β-L-fucose 
• 365-07-1 thymidine 5'-phosphate 
• 66-22-8 uracil 

Relevant articles and documents

PPN Pyrophosphate: A New Reagent for the Preparation of Nucleoside Triphosphates

Tris{bis(triphenylphosphoranylidene) ammonium} (PPN) pyrophosphate was accessed via aqueous precipitation and desiccation. The reagent was investigated as a replacement for highly hygroscopic alkylammonium salts in Ludwig-Yoshikawa reactions for the preparation of nucleoside-5′-triphosphates.

REVERSIBLE TERMINATORS FOR DNA SEQUENCING AND METHODS OF USING THE SAME

The present disclosure provides methods of sequencing polynucleotides and compounds, compositions for sequencing of polynucleotides, and synthesis of such compositions. The chemical compounds include nucleotides and their analogs which possess a sugar moiety comprising a cleavable chemical group capping the 3'-OH group and a base, but without covalently bounded dye. The cleavable chemical group is reactive to form covalent bond(s) with a dye used to confirm the presence of the expected base-pairing. The cleavable chemical group capping the 3'OH group can be removed together with the covalently bounded dye. Furthermore, after the cleavable chemical group is cleaved, the free 3'-OH group can be active in continued elongation. Example chemical compounds according to the present disclosure are shown as Formulas (II) and (V).

Lipophilic Triphosphate Prodrugs of Various Nucleoside Analogues

The antiviral efficacy of many nucleoside analogues is strongly dependent on their intracellular activation by host cellular kinases to yield ultimately the bioactive nucleoside analogue triphosphates (NTP). The metabolic conversion of nucleoside analogues into their triphosphates often proceeds insufficiently. We developed a nucleoside triphosphate (NTP) delivery system (the TriPPPro approach), in which the γ-phosphate is covalently modified by two different biodegradable masking units, one is the acyloxybenzyl (AB) moiety and the other is the alkoxycarbonyloxybenzyl (ACB) group. Such compounds formed NTPs with high selectivity by an enzyme-triggered mechanism in human T-lymphocyte CEM cell extracts loosing first the AB moiety, followed by the ACB group. This enables the bypass of all steps of the intracellular phosphorylation. This approach was applied here to convert some modestly active or even inactive nucleoside analogues into powerful biologically active metabolites. Potent antiviral activity profiles were obtained depending on the lipophilicity of the TriPPPro-NTP prodrugs against HIV-1 and HIV-2 replication in cultures of infected wild-type CD4+ CEM T-cells and more importantly in thymidine kinase-deficient CD4+ T-cells (CEM/TK-). This TriPPPro strategy offers high potential for future antiviral and antitumoral chemotherapies.