2239-64-7

Basic information

• Product Name: 6-MERCAPTOPURINE-2'-DEOXYRIBOSIDE
• Synonyms: 2’-deoxy-6-thio-inosin;2’-deoxy-6-thioinosine;6-mercaptopurinedeoxyriboside;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purine-6(1h)-thiol;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purine-6(1h)-thion;6-MERCAPTOPURINE-2'-DEOXYRIBONUCLEOSIDE;6-MERCAPTOPURINE-2'-DEOXYRIBOSIDE;DEOXYTHIOINOSINE
• CAS NO: 2239-64-7
• Molecular Formula: C₁₀H₁₂N₄O₃S
• Molecular Weight: 268.29
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 2239-64-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 665.9°Cat760mmHg
• Flash Point: 356.5°C
• Appearance: /
• Density: 1.87g/cm³
• Vapor Pressure: 1.23E-18mmHg at 25°C
• Refractive Index: 1.863
• Storage Temp.: −20°C
• CAS DataBase Reference: 6-MERCAPTOPURINE-2'-DEOXYRIBOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-MERCAPTOPURINE-2'-DEOXYRIBOSIDE(2239-64-7)
• EPA Substance Registry System: 6-MERCAPTOPURINE-2'-DEOXYRIBOSIDE(2239-64-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: UP0762000
• Hazardous Substances Data: 2239-64-7(Hazardous Substances Data)

Usage

Chemical Properties

solid

InChI:InChI=1/C10H12N4O3S/c15-2-6-5(16)1-7(17-6)14-4-13-8-9(14)11-3-12-10(8)18/h3-7,15-16H,1-2H2,(H,11,12,18)

Upstream product

• 951-78-0 2'-deoxyuridine 
• 157930-09-1 6-Mercaptopurine 
• 50-89-5 thymidine 
• 890-38-0 2-deoxyinosine 
• 50-44-2 6-mercaptopurine 
• 87-42-3 6-chloropurine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 687983-85-3 1-[9-((2R,4S,5R)-4-Acetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-pyridinium 
• 106568-79-0 9-(3',5'-di-O-acetyl-2'-deoxy-β-D-erythro-pentofuranosyl)-1H-purine-6(9H)-one 
• 50-44-2 6H-purine-6-thione 
• 145060-59-9 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-thioxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 91713-46-1 6-Chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine 

Downstream Products

• 139887-94-8 2,2-Dimethyl-propionic acid 9-{(2R,4S,5R)-4-acetoxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylsulfanylmethyl ester 
• 139887-93-7 2,2-Dimethyl-propionic acid 9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-ylsulfanylmethyl ester 
• 145060-61-3 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-deoxy-6-(2,4-dinitrophenyl)thiopurine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite 
• 145060-62-4 (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[6-(2,4-dinitro-phenylsulfanyl)-purin-9-yl]-tetrahydro-furan-3-ol 
• 163882-50-6 (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furan-3-ol 
• 194918-44-0 3-(9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-ylsulfanyl)-propionitrile 
• 23526-11-6 S-methylthiodeoxyinosine 
• 145060-60-2 (2R,3S,5R)-5-[6-(2,4-Dinitro-phenylsulfanyl)-purin-9-yl]-2-hydroxymethyl-tetrahydro-furan-3-ol 
• 139887-92-6 9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1,9-dihydro-purine-6-thione 

Relevant articles and documents

The enzymic synthesis of 6-mercaptopurine deoxyriboside.

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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.

Post-synthetic introduction of labile functionalities onto purine residues via 6-methylthiopurines in oligodeoxyribonucleotides

Two methods are described for the preparation of oligodeoxynucleotides containing 6-methylthiopurine residues. 6-Methylthiopurine phosphoramidite (6) has been prepared and incorporated into oligomers. Methylation with methyl iodide of 6-thiopurine (or 6-thioguanine) in oligomers also exclusively produces oligomers containing 6-methylthiopurine (or 6-methylthioguanine). The methylthio group at defined purine residues in the deprotected oligomers can be oxidized selectively and converted at the final step into various functional groups including radioactive 35S-thio group, a useful tag for cross-linking studies.