2564-35-4

Basic information

• Product Name: 2'-DEOXYGUANOSINE-5'-TRIPHOSPHORIC ACID, DISODIUM
• Synonyms: 2'-DEOXYGUANOSINE-5'-TRIPHOSPHORIC ACID, DISODIUM;2'-DEOXYGUANOSINE-5'-TRIPHOSPHORIC ACID, LITHIUM;2'-DEOXY-GUANOSINE-5'-TRIPHOSPHATE LITHIUM SALT;DGTP, LI;DGTP LI-SALT;DGTP, NA2H2;2’-deoxy-guanosin5’-(tetrahydrogentriphosphate);2’-deoxyguanosine5’-(tetrahydrogentriphosphate)
• CAS NO: 2564-35-4
• Molecular Formula: C₁₀H₁₆N₅O₁₃P₃
• Molecular Weight: 551.14
• EINECS: 219-887-2
• Mol File: 2564-35-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 2.63±0.1 g/cm3(Predicted)
• PKA: 0.97±0.50(Predicted)
• CAS DataBase Reference: 2'-DEOXYGUANOSINE-5'-TRIPHOSPHORIC ACID, DISODIUM(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-DEOXYGUANOSINE-5'-TRIPHOSPHORIC ACID, DISODIUM(2564-35-4)
• EPA Substance Registry System: 2'-DEOXYGUANOSINE-5'-TRIPHOSPHORIC ACID, DISODIUM(2564-35-4)

Safety Data

• Hazardous Substances Data: 2564-35-4(Hazardous Substances Data)

Usage

General Description

2'-Deoxyguanosine-5'-triphosphoric acid, disodium is a chemical compound often used in biological research, particularly in the area of medicine and biochemistry. It is a salt form of deoxyguanosine triphosphate (dGTP), a deoxyribonucleotide which is essential for DNA replication and repair in the cellular environment. 2'-DEOXYGUANOSINE-5'-TRIPHOSPHORIC ACID, DISODIUM plays a crucial role in the synthesis of DNA and RNA by acting as a building block. It is of significant interest in research concerning DNA replication, mutation, and cellular function. However, it is important to handle it with care as it may be harmful if inhaled, swallowed, or comes in contact with skin.

Upstream product

• 902-04-5 2'-deoxyguanosine 5'-monophosphate 
• 3493-09-2 5′-deoxyguanosine diphosphate 
• 961-07-9 2'-Deoxyguanosine 
• 56-65-5 ATP 
• 58-64-0 adenosine 5'-diphosphate 

Downstream Products

• 902-04-5 2'-deoxyguanosine 5'-monophosphate 
• 38168-82-0 glyceric acid 1,3-biphosphate 
• 139307-94-1 2'-deoxy-7,8-dihydro-8-oxoguanosine-5'-triphosphate 

Relevant articles and documents

Anabolism of amdoxovir: Phosphorylation of dioxolane guanosine and its 5′-phosphates by mammalian phosphotransferases

Amdoxovir [(-)-β-D-2,6-diaminopurine dioxolane, DAPD], the prodrug of dioxolane guanosine (DXG), is currently in Phase I/II clinical development for the treatment of HIV-1 infection. In this study, we examined the phosphorylation pathway of DXG using 15 purified enzymes from human (8), animal (6), and yeast (1) sources, including deoxyguanosine kinase (dGK), deoxycytidine kinase (dCK), high Km 5′-nucleotidase (5′-NT), guanylate (GMP) kinase, nucleoside monophosphate (NMP) kinase, adenylate (AMP) kinase, nucleoside diphosphate (NDP) kinase, 3-phosphoglycerate (3-PG) kinase, creatine kinase, and pyruvate kinase. In addition, the metabolism of 14C-labeled DXG was studied in CEM cells. DXG was not phosphorylated by human dCK, and was a poor substrate for human dGK with a high Km (7 mM). Human 5′-NT phosphorylated DXG with relatively high efficiency (4.2% of deoxyguanosine). DXG-MP was a substrate for porcine brain GMP kinase with a substrate specificity that was 1% of dGMP. DXG-DP was phosphorylated by all of the enzymes tested, including NDP kinase, 3-PG kinase, creatine kinase, and pyruvate kinase. The BB-isoform of human creatine kinase showed the highest relative substrate specificity (47% of dGDP) for DXG-DP. In CEM cells incubated with 5 μM DXG for 24 h, 0.015 pmole/106 cells (～7.5 nM) of DXG-TP was detected as the primary metabolite. Our study demonstrated that 5′-nucleotidase, GMP kinase, creatine kinase, and NDP kinase could be responsible for the activation of DXG in vivo.

Synthetic method of nucleoside tetraphosphate

The invention discloses a synthetic method of nucleoside tetraphosphate. The synthetic method comprises the steps of carrying out selective phosphorylation reaction by virtue of nucleoside and a cyclic phosphorylation reagent, and carrying out oxidation and hydrolysis loop opening, so as to obtain nucleoside tetraphosphate. The structure of the cyclic phosphorylation reagent is represented by a formula I (shown in the description). According to the synthetic method, 5'-nucleoside tetraphosphate is selectively generated from nucleoside under the effect of the high-selectivity phosphorylation reagent, and 3'-OH (and 2'-OH) does not need to be protected in the process, namely that the generaiton of 3'(and 2'-)tetraphosphate can be effectively inhibited. Nucleoside tetraphosphate synthesized by virtue of the method has wide use ranges in the biology fields of DNA sequencing, labeling, extension and the like; currently, the selling prices is expensive, a synthetic method is complex, the reaction selectivity is poor; and the synthetic method provided by the invention is good in selectivity and easy in separation and purification, required experimental conditions are simple, and the synthetic processes are all conventional chemical reactions, so that the synthetic method is applicable to large-scale popularization and use.

An improved protection-free one-pot chemical synthesis of 2′-deoxynucleoside-5′-triphosphates

□ A facile, straightforward, reliable, and an efficient method for the gram-scale chemical synthesis of both purine deoxynucleotides such as 2 ′-deoxyguanosine-5 ′-triphosphate (dGTP) and 2 ′- deoxyadenosine-5′-triphosphate (dATP) and pyrimidine deoxynucleotides such as 2 ′-deoxycytidine- 5 ′-triphosphate (dCTP), thymidine-5 ′-triphosphate (TTP), and 2 ′-deoxyuridine-5 ′-triphosphate (dUTP) starting from the corresponding nucleoside is described. This improved "one-pot, three step"Ludwig synthetic strategy involves the monophosphorylation of nucleoside followed by reaction with tributylammonium pyrophosphate and hydrolysis of the resulting cyclic intermediate to provide the corresponding dNTP in good yields (65%-70%). Copyright Taylor and Francis Group, LLC.