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
• Article Data: 12

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

Description

2',3'-Dideoxyguanosine, also known as DDG, is a nucleoside analog derived from the natural nucleoside guanosine. It is characterized by the absence of the 2' and 3' hydroxyl groups on the ribose sugar moiety, which distinguishes it from the parent compound. DDG exhibits solid-state chemical properties and has been extensively studied for its potential therapeutic applications.

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

• 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 
• 85326-13-2 N-(9-(5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide 
• 4097-22-7 2',3'-Dideoxyadenosine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 69655-05-6 Dideoxyinosine 
• 68-94-0 hypoxanthine 
• 118-00-3 G 
• 119794-37-5 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-2',3'-bis-O-<<(β-cyanoethyl)thio>thiocarbonyl>guanosine 
• 119794-50-2 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-2',3'-bis-O-<(methylthio)thiocarbonyl>guanosine 
• 119794-38-6 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-2',3'-O-thionocarbonylguanosine 
• 89494-39-3 5'-O-(tert-butyldimethylsilyl)-N²-isobutyrylguanosine 
• 119794-39-7 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine 
• 119794-40-0 N²-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine 
• 64350-24-9 N²-isobutyryl-2'-deoxyguanosine 

Downstream Products

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

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.

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.

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.