4546-70-7

Basic information

• Product Name: 2,6-Diaminopurine 2'-deoxyriboside
• Synonyms: 2,6-DIAMINOPURINE-2'-DEOXYRIBOSIDE;2,6-diaminopurinedeoxyriboside;2-amino-2’-deoxy-adenosin;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-2,6-diamino-9h-purin;2'-Deoxy-2-aminoadenosine;2,6-Diaminopurine Deoxyribose;2,6-DIAMINPURINE-2''-DEOXYRIBOSIDE;2, 6-DIAMINOPURINE 2''-DEOXYRIBOSIDE (2-AMINO-2''-DEOXYADENOSINE)
• CAS NO: 4546-70-7
• Molecular Formula: C₁₀H₁₄N₆O₃
• Molecular Weight: 266.26
• EINECS: 200-001-2
• Product Categories: Bases & Related Reagents;Nucleotides;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 4546-70-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 144°C
• Boiling Point: 748.4 °C at 760 mmHg
• Flash Point: 406.4 °C
• Appearance: White to Off-white/Powder
• Density: 2.08 g/cm³
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Sonicated
• PKA: 13.79±0.60(Predicted)
• CAS DataBase Reference: 2,6-Diaminopurine 2'-deoxyriboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diaminopurine 2'-deoxyriboside(4546-70-7)
• EPA Substance Registry System: 2,6-Diaminopurine 2'-deoxyriboside(4546-70-7)

Safety Data

• WGK Germany: 3
• RTECS: UO7523300
• Hazardous Substances Data: 4546-70-7(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

2,6-Diaminopurine-2’-deoxyriboside is a nucleoside analogs synthesized to interfere with DNA metabolism. A derivative of 2,6-Diaminopurine (D416580), which can be used as analyte for biological and analytical studies of incorporation of unnatural nucleotides into mutant tRNA and proteins.

Upstream product

• 1904-98-9 2,6-diaminopurine 
• 50-89-5 thymidine 
• 128790-76-1 2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 
• 961-07-9 2'-Deoxyguanosine 
• 890-38-0 2-deoxyinosine 
• 38925-80-3 2,6-Dichloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-purine 
• 951-78-0 2'-deoxyuridine 
• 1904-98-9 2,6-diaminopurine 
• 81102-46-7 2,6-diamino-8-bromo-9-(2'-O-tosyl-β-D-ribufuranosyl)-purine 
• 79999-39-6 2',3',5'-tri-O-acetyl-2-chloroadenosine 
• 37070-11-4 8,2'-anhydro-8-mercaptoguanosine 
• 81102-48-9 2-acetamido-8,2'-anhydro-6-chloro-8-mercapto-9-(3',5'-O-diacetyl-β-D-arabinofuranosyl)purine 
• 81102-44-5 9-(β-D-ribofuranosyl)-2,6-diamino-8-bromopurine 
• 2096-10-8 adenosine-2-amine 

Downstream Products

• 1904-98-9 2,6-diaminopurine 
• 156549-48-3 5'-O-dimethoxytrityl-N²,N⁶-bis(phenoxyacetyl)-2,6-diaminopurine 2'-deoxyriboside 
• 676458-04-1 9-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-4-C-ethynyl-ribo-pentofuranosyl)-2,6-dibenzamidopurine 
• 583047-67-0 9-(3,5-di-O-tert-butyldimethylsilyl-4-C-cyano-2-deoxy-ribo-pentofuranosyl)-2,6-dibenzamidopurine 
• 583047-65-8 C₅₂H₅₆N₆O₈Si 

Relevant articles and documents

6-O-(Pentafluorophenyl)-2'-deoxyguanosine: A Versatile Synthon for Nucleoside and Oligonucleotide Synthesis

The 6-O-(pentafluorophenyl)-2'-deoxyguanosine derivative 2a can be used to generate in high yield 6-O-methyl-2'-deoxyguanosine, 2,6-diamino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine, and related derivatives.Further, after appropriate protection and derivatization, 2a can be incorporated into oligonucleotides and there used for postsynthetic oligonucleotide modification.This approach is particularly useful for preparation of oligonucleotides containing 2,6-diaminopurine residues or their 6-alkylamino derivatives.In addition, reaction of 2a, or oligonucleotides containing it, with 4-(dimethylamino)pyridine (DMAP) gives a fluorescent guanine-DMAP adduct.

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.

THERMOSTABLE BIOCATALYST COMBINATION FOR NUCLEOSIDE SYNTHESIS

The present invention relates to a transglycosylation method for the preparation of natural and synthetic nucleosides using a uridine phosphorylase (PyNPase, E.C. 2.4.2.3), a purine nucleoside phosphorylase (PNPase, E.C. 2.4.2.1), or a combination thereof. These biocatalysts may be used as such, or by means of host cells transformed with vectors comprising recombinant DNA gene derived from hyperthermophilic archaea and encoding for the PyNPase and PNPase enzymes.