85326-06-3

Basic information

• Product Name: 2',3'-Dideoxyguanosine
• Synonyms: 2',3'-DIDEOXYGUANOSINE;DDG;BETA-D-2',3'-DIDEOXYGUANOSINE;2',3'-Didioxyguanosine;2',3'-Dideoxy-D-guanosine;2-Amino-9-[5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;ddGuo;2-AMino-9-((2R,5S)-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
• CAS NO: 85326-06-3
• Molecular Formula: C₁₀H₁₃N₅O₃
• Molecular Weight: 251.24
• EINECS: 2017-001-1
• Product Categories: Enzyme Inhibitors;Enzyme Inhibitors by Type;Substrate Analogs
• Mol File: 85326-06-3.mol

Chemical Properties

• Boiling Point: 632.1 °C at 760 mmHg
• Flash Point: 336.1 °C
• Appearance: White to Off-white/Powder
• Density: 1.91 g/cm³
• Storage Temp.: 2-8°C
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: 2',3'-Dideoxyguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Dideoxyguanosine(85326-06-3)
• EPA Substance Registry System: 2',3'-Dideoxyguanosine(85326-06-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 85326-06-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2',3'-Dideoxyguanosine is used as an antiviral agent for its anti-HIV activities. It has been modified and evaluated for its efficacy in inhibiting the replication of the Human Immunodeficiency Virus (HIV) in cell-based assays. The unique structural modification of DDG allows it to interfere with the viral replication process, making it a promising candidate for the development of antiretroviral therapies.
Additionally, due to its nucleoside analog nature, 2',3'-Dideoxyguanosine may also have potential applications in other therapeutic areas, such as the treatment of other viral infections or as a research tool for studying nucleic acid metabolism and function. However, further research and development are required to explore these possibilities and to optimize the drug's safety and efficacy profile for clinical use.

Upstream product

• 85326-13-2 N-(9-(5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide 
• 98056-51-0 Acetic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-methoxythiocarbonyloxy-tetrahydro-furan-2-ylmethyl ester 
• 98056-55-4 2,2-Dimethyl-propionic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-methoxythiocarbonyloxy-tetrahydro-furan-2-ylmethyl ester 
• 177779-53-2 2-Amino-9-[(2R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one 
• 961-07-9 2'-Deoxyguanosine 
• 51549-33-8 2’-deoxy-5’-O-tert-butyldimethylsilylguanosine 
• 177779-52-1 Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester 
• 72560-68-0 5'-O-acetyl-2'-deoxyguanosine 
• 98056-54-3 2,2-Dimethyl-propionic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 
• 64350-24-9 N²-isobutyryl-2'-deoxyguanosine 
• 119794-40-0 N²-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine 
• 119794-39-7 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine 
• 89494-39-3 5'-O-(tert-butyldimethylsilyl)-N²-isobutyrylguanosine 
• 119794-38-6 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-2',3'-O-thionocarbonylguanosine 

Downstream Products

• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 122999-44-4 2,3-Didesoxy-β-D-glycero-pentofuranose 
• 1350456-24-4 C₃₁H₃₁N₅O₅ 
• 1350456-25-5 C₃₇H₃₉N₅O₈ 
• 1350456-26-6 C₃₅H₃₇N₅O₆ 

Relevant articles and documents

Enzymatic Synthesis of Therapeutic Nucleosides using a Highly Versatile Purine Nucleoside 2’-DeoxyribosylTransferase from Trypanosoma brucei

The use of enzymes for the synthesis of nucleoside analogues offers several advantages over multistep chemical methods, including chemo-, regio- and stereoselectivity as well as milder reaction conditions. Herein, the production, characterization and utilization of a purine nucleoside 2’-deoxyribosyltransferase (PDT) from Trypanosoma brucei are reported. TbPDT is a dimer which displays not only excellent activity and stability over a broad range of temperatures (50–70 °C), pH (4–7) and ionic strength (0–500 mM NaCl) but also an unusual high stability under alkaline conditions (pH 8–10). TbPDT is shown to be proficient in the biosynthesis of numerous therapeutic nucleosides, including didanosine, vidarabine, cladribine, fludarabine and nelarabine. The structure-guided replacement of Val11 with either Ala or Ser resulted in variants with 2.8-fold greater activity. TbPDT was also covalently immobilized on glutaraldehyde-activated magnetic microspheres. MTbPDT3 was selected as the best derivative (4200 IU/g, activity recovery of 22 %), and could be easily recaptured and recycled for >25 reactions with negligible loss of activity. Finally, MTbPDT3 was successfully employed in the expedient synthesis of several nucleoside analogues. Taken together, our results support the notion that TbPDT has good potential as an industrial biocatalyst for the synthesis of a wide range of therapeutic nucleosides through an efficient and environmentally friendly methodology.

Synthesis and anti-HIV activity of a series of 6-modified 2′,3′-dideoxyguanosine and 2′,3′-didehydro-2′, 3′-dideoxyguanosine analogs

In search of potential 2′,3′-dideoxyguanosine (ddG) and 2′,3′-didehydro-2′,3′-dideoxyguanosine (D4G) prodrugs, a series of 6-modified ddG, D4G analogs were synthesized and evaluated for their anti-HIV activities and cytotoxities in cell-based assays. All analogs showed low cytotoxicities and some of them displayed benign anti-HIV activities. The active triphosphate forms in vivo, ddGTP and D4TTP, were also synthesized by a novel and facile one-pot method. The recognition of ddGTP and D4TTP by Taq, Therminater DNA polymerase and HIV reverse transcriptase (RT) incorporated in DNA/RNA strands were investigated by a non-radioactivity method and K m were determined. A series of 6-modified 2′,3′- dideoxyguanosine and 2′,3′-didehydro-2′,3′- dideoxyguanosine analogs were synthesized. Anti-HIV activity was investigated in cell-based assay. ddGTP was synthesized as well as D4TTP by a novel one-pot method, and the incorporation efficiencies recognized by DNA polymerase and HIV reverse transcriptase (HIV RT) were evaluated. Copyright

Specific lipid conjugates to nucleoside diphosphates and their use as drugs

The present invention concerns new phospholipid derivatives of nucleosides of the general formula (I) in which R1represents a straight-chained or branched, saturated or unsaturated aliphatic residue with 9-14 carbon atoms which can optionally be substituted once or several times; R2can represent a straight-chained or branched, saturated or unsaturated aliphatic residue with 8-12 carbon atoms which can optionally be substituted once or several times; m is 2 or 3; A can represent a methylene group or an oxygen; Nuc can be a nucleoside or a residue derived from a nucleoside derivative; and tautomers thereof and their physiologically tolerated salts of inorganic and organic acids and bases as well as pharmaceutical preparations containing these compounds.

Compositions for treating viral infections, and methods therefor

Methods and combinations of an agent that promotes DNA synthesis in a virally-targeted cell and a nucleoside analogue having antiviral activity are provided for treating a viral infection in a subject in need thereof. Such compositions are particularly effective where the subject has resistance to a nucleoside analogue, where the subject has resting cellular reservoirs of such a virus, or to induce a post-treatment period of replication incompetence of such a virus.

Process for the production of asymmetrical phosphoric acid diesters

The present invention concerns a process for the production of asymmetrical phosphoric acid diesters. The process is characterized in that a phosphoric acid ester is condensed with a compound containing hydroxy groups in the presence of an arylsulfonic acid chloride and an organic base, the residue of evaporation is stirred out with an organic solvent after the hydrolysis, the arylsulfonic acid pyridine salt which forms is nearly completely crystallized and recycled, the lipid derivative that is formed is precipitated as a sparingly soluble salt by addition of a solution containing alkaline-earth ions and isolated, the sparingly soluble salt is isolated as the free acid in an organic solvent by suspension in a water-immiscible organic solvent and a dilute aqueous mineral acid, the crude product is purified if desired, by means of preparative chromatography on a RP phase and subsequently the free acid is converted if desired into any desired salt.

Synthesis of 2′,3′-dideoxypurinenucleosides via the palladium catalyzed reduction of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)purine derivatives

Practical method to produce 2′,3′-dideoxypurinenucleosides from 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)purines (1) was developed. High ratio of 2′,3′-dideoxynucleoside to 3′-deoxyribonucleoside was obtained by selecting the reaction conditions (solvent, pH and/or base), or changing 2′-acyloxy leaving group. The reaction mechanism was studied by deuteration experiments of 1a and 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine (12).

Synthesis and 1H and 13C NMR spectral characteristics of 8-bromo-2′,3′-dideoxyguanosine and 8-bromo-2′,3′-dideoxyinosine

Reaction of 2′,3′-dideoxyguanosine 1a as 5′-O-tert-butyldimethylsilyl derivative 1b and 2′,3′-dideoxyinosine 2a with bromine in acetate buffer conducted in heterogeneous medium afforded 8-bromo-2′,3′-dideoxyguanosine 3a (44% after deprotection) and 8-bromo-2′,3′-dideoxyinosine 4a (12%) respectively. The change of conformational preferences anti → syn on 8-bromo substitution of 2′,3′-dideoxynucleosides is reflected in the 1H and 13C NMR spectra by characteristic shifts of H-2′, H-3′, C-2′ and C-3′ signals.

Synergistic antiviral nucleoside combinations

An antiviral composition comprising in combination an effective antiviral amount of 3'-fluoro-2',3'-dideoxy nucleoside compound I of the formula STR1 wherein B is adenine, thymine, guanine, cytosine, inosine, uracil, 5-ethyluracil, 2,6-diaminopurine; and an effective antiviral amount of 2',3'-dideoxy nucleoside compound II of the formula STR2 wherein X is N3 or H or together with Y forms an additional carbon-carbon bond, Y and Z are independently H, OH or F, and B is adenine, thymine, guanine, cytosine, inosine, uracil, 5-ethyluracil, 2,6-diaminopurine, and a physiologically acceptable carrier.

Antiviral agents

Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.

4'-substituted nucleosides

Nucleosides compounds of Formula I: STR1 wherein B is a purine or a pyrimidine; X and X' are H; Y is H; Y' is OH, F or H; or Y' and X' together makes a bond; Z is STR2 where n is zero, one, two or three; or Y' and Z together form a cyclic phosphate ester; Z' is --CN, --CH3, CH2 N3 or --CH2 J, where J is a halogen atom; or Z' and Y' together are --CH2 O--; and pharmaceutically acceptable esters, ethers, amides, N-acyl moieties and salts thereof.