107550-73-2

Basic information

• Product Name: 2,6-diaminopurine 2',3'-dideoxyriboside
• Synonyms: 2,6-diaminopurine 2',3'-dideoxyriboside;2,6-Diamino-9-(2,3-dideoxy-β-D-ribofuranosyl)-9H-purine;Adenosine, 2-aMino-2',3'-dideoxy-;2,6-Diamino-2',3'-dideoxypurine-9-ribofuranoside;2-Amino-2',3'-dideoxyadenosine;2-NH2-2',3'-ddA
• CAS NO: 107550-73-2
• Molecular Formula: C10H14N6O2
• Molecular Weight: 250.25716
• Mol File: 107550-73-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 655.1°Cat760mmHg
• Flash Point: 350°C
• Appearance: /
• Density: 1.91g/cm³
• CAS DataBase Reference: 2,6-diaminopurine 2',3'-dideoxyriboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-diaminopurine 2',3'-dideoxyriboside(107550-73-2)
• EPA Substance Registry System: 2,6-diaminopurine 2',3'-dideoxyriboside(107550-73-2)

Safety Data

• Hazardous Substances Data: 107550-73-2(Hazardous Substances Data)

Usage

Structure

Purine base (2,6-diaminopurine) attached to a 2',3'-dideoxyribose sugar

Resistance to degradation

Resistant to degradation by enzymes that typically act on nucleosides

Biological activity

Potent and specific inhibitor of serine/threonine protein kinases

Research applications

Used in biochemistry research

Potential properties

Anti-tumor, anti-viral, and ability to induce DNA damage and inhibit cell growth

Molecular tool

Investigated for its potential as a molecular tool to study protein phosphorylation and signal transduction pathways in cells.

Upstream product

• 4097-22-7 2',3'-Dideoxyadenosine 
• 1904-98-9 2,6-diaminopurine 
• 69655-05-6 Dideoxyinosine 
• 2096-10-8 adenosine-2-amine 
• 413570-54-4 9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-6-chloro-9H-purin-2-ylamine 
• 141684-95-9 2-amino-6-chloro-9-(2,3-dideoxy-β-D-glycero-pent-enofuranosyl)-9H-purine 
• 413570-52-2 2-amino-9-(5-O-tert-butyldimethylsilyl-2,3-O-thiocarbonyl-β-D-ribofuranosyl)-6-chloropurine 
• 413570-50-0 2-amino-9-(5-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-6-chloropurine 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 109881-25-6 2,6-diamino-9-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)purine 

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.

Nucleic Acid Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogues

Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (α-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents.Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time.Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino- 2-fluoropurine riboside.Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH(-)) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds.Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides.Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides.A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses.New 13C NMR data for several types of unsaturated-sugar nucleosides are tabulated.These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.

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.