16006-64-7

Usage

Uses

Used in Chemical Research:
6-methylpurine 2'-deoxyriboside is used as a model compound for [understanding the chemical behavior and reactivity of similar nucleosides] because of its structural similarity to other nucleosides, which aids in studying their properties and interactions within biological systems.
Used in Biological Research:
In biological research, 6-methylpurine 2'-deoxyriboside is used as an intermediate in [the biosynthesis of certain modified nucleosides in DNA], which is essential for understanding the mechanisms of DNA modification and its implications on genetic information and regulation.
Used in Cancer Treatment Research:
6-methylpurine 2'-deoxyriboside is investigated for its potential use in [cancer treatment] due to its role in promoting cell growth and its possible influence on cancer cell behavior, offering a new avenue for therapeutic intervention in oncology.
Used in Drug Development:
6-methylpurine 2'-deoxyriboside is also considered in drug development as a [potential biological and therapeutic agent], given its potential impact on cell growth and its presence in the biosynthesis of DNA, which could lead to the creation of novel pharmaceuticals targeting specific genetic or cellular processes.

Upstream product

• 181475-59-2 9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-methylpurine 
• 52162-55-7 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride 
• 20289-65-0 9-(3,5-di-O-acetyl-2-deoxy-β-D-ribofuranosyl)-6-methylpurine 
• 156517-72-5 6-chloro-9-(3,5-bis-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)purine 
• 17318-24-0 3',5'-di-O-acetyl-2'-deoxyadenosine 
• 890-38-0 2-deoxyinosine 
• 2004-03-7 6-methylpurine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 215372-43-3 Thiocarbonic acid O-phenyl ester O-[(2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester 
• 215372-40-0 Acetic acid (2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 
• 215372-42-2 (2R,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 182195-43-3 2'-O-acetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)inosine 
• 87791-89-7 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)inosine 
• 91713-46-1 6-Chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine 

Downstream Products

• 17039-17-7 2-deoxy–α-D-ribose 1-phosphate 
• 2004-03-7 6-methylpurine 

Relevant academic research and scientific papers

A novel approach to synthesis of 2'-deoxy-β-D-ribonucleosides via transglycosylation of 6-oxopurine ribonucleosides

A novel method of synthesis of 2'-deoxy-β-D-ribonucleosides via transglycosylation of 6-oxopurine ribonucleosides is exemplified for conversion of inosine into 6-metylpurine 2'-deoxyriboside (5). The method offers high regio- and stereoselectivity as well

Stereoselective synthesis of 6-methyl-9-(2-deoxy-β-D-erythro- pentofuranosyl)purine

The coupling of the sodium salt of 6-methylpurine with 2-deoxy-3,5-di- O-p-toluoyl-α-D-erythro-pentofuranosyl chloride in acetonitrile gives the di-O-p-toluoyl protected 9-β nucleoside regio- and stereo-selectively in good yield. Methoxide deprotection followed by preparative hplc then affords pure 6-methyl-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine.

N8-Glycosylated 8-Azapurine and Methylated Purine Nucleobases: Synthesis and Study of Base Pairing Properties

In this report, we present the synthesis of N8-glycosylated 8-aza-2-methylhypoxanthine and 8-aza-6-thiohypoxanthine 2′-deoxynucleosides as well as methylated 2′-deoxynebularine derivatives. In vitro base pairing properties between each modified and canonical nucleobase were studied. As demonstrated by Tm, incorporation of the modified bases in DNA resulted, with few exceptions, in low stability of duplexes. Modified bases studied in this report are preferentially recognized by T (for N8-glycosylated 8-aza-2-methylhypoxanthine and methylated purines) and G (N8-glycosylated 8-aza-2-methylhypoxanthine). The base pair formed between N8-glycosylated 8-aza-6-thiohypoxanthine and N9-glycosylated 2-methyl-6-thiohypoxanthine (X2:X6) showed, to some extent, an orthogonal interaction. Based on Tm studies, the only potential self-pairing system is formed by the N8-glycosylated 8-aza-6-thiohypoxanthine nucleoside (X2) but only in the absence of canonical G and T. This study indicated that the canonical thymine base is the preferential base partner of methylated purine bases.

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.

The catalytic power of uracil DNA glycosylase in the opening of thymine base pairs

Uracil DNA glycosylase (UNG) locates uracil and its structural congener thymine in the context of duplex DNA using a base flipping mechanism. NMR imino proton exchange measurements were performed on free and UNG-bound DNA duplexes in which a single thymin

Convenient syntheses of 6-methylpurine and related nucleosides

Efficient methods for the synthesis of 6-methylpurine (3), 9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methylpurine (8), and 6-methyl-9-β-D-ribofuranosylpurine (5) are described. Methodology involving the (Ph3P)4Pd catalyzed cross-coupling reaction of CH3ZnBr with several different 6-chloropurine derivatives is described in high yield. This methodology now provides a facile and high-yielding synthesis of 8, which is needed in significant amounts for studies in cancer gene therapy.

Gene therapy of cancer: activation of nucleoside prodrugs with e. colipurine nucleoside phosphorylase

During the last few years, many gene therapy strategies have been developed for various disease targets. The development of anticancer gene therapy strategies to selectively generate cytotoxic nucleoside or nucleotide analogs is an attractive goal. One such approach involves the delivery of herpes simplex virus thymidine kinase followed by the acyclic nucleoside analog ganciclovir. We have developed another gene therapy methodology for the treatment of cancer that has several significant attributes. Specifically, our approach involves the delivery of E. coli purine nucleoside phosphorylase, followed by treatment with a relatively non-toxic nucleoside prodrug that is cleaved by the enzyme to a toxic compound. .This presentation describes the concept, details our search for suitable prodrugs, and summarizes the current biological data. Copyright

SYNTHESIS OF 2-DEOXY-β-D-RIBONUCLEOSIDES AND2,3-DIDEOXY.β-D-PENTOFURANOSIDES ON IMMOBILIZED BACTERIAL CELLS

Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs.All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series.Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety.The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom.On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives.Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed.The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-deoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-deoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.