53458-28-9

Basic information

• Product Name: 2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
• Synonyms: 9-(5'-deoxy-5'-(methylthio)-xylofuranosyl)adenine;9-(5'Deoxy-5'-(methylthio)-beta-D-xylofuranosyl)adenine;9-Dmxa;9H-Purin-6-amine, 9-(5-S-methyl-5-thio-beta-D-arabinofuranosyl)-;Xylo-mta;Xylosyl-methylthio-adenosine
• CAS NO: 53458-28-9
• Molecular Formula: C₁₁H₁₅N₅O₃S
• Molecular Weight: 297.33
• Mol File: 53458-28-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 642.7°Cat760mmHg
• Flash Point: 342.5°C
• Appearance: /
• Density: 1.85g/cm³
• Vapor Pressure: 2.13E-17mmHg at 25°C
• Refractive Index: 1.843
• CAS DataBase Reference: 2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol(53458-28-9)
• EPA Substance Registry System: 2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol(53458-28-9)

Safety Data

• Hazardous Substances Data: 53458-28-9(Hazardous Substances Data)

Usage

Purine base

Derived from adenine, a component of DNA and RNA.

Sulfur-methyl group

Provides a sulfhydryl functionality, important for reactivity and biological activity.

Oxolane diol ring

A five-membered ring containing both an oxygen and a hydroxyl group, contributing to stability and chelating properties.

Potential applications

Medicinal chemistry, biochemistry, and pharmaceuticals due to its important biological and chemical properties.

InChI:InChI=1/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8+,11-/m1/s1

Upstream product

• 65562-53-0 9-(5-chloro-5-deoxy-β-D-arabinofuranosyl)adenine 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 66224-66-6 adenine 

Relevant articles and documents

Anticancer and antiviral effects and inactivation of S-adenosyl-L- homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues

Selectively protected adenine nucleosides were converted into 5'- carboxaldehyde analogues by Moffatt oxidation (dimethyl sulfoxide/dicyclohexylcarbodiimide/dichloroacetic acid) or with the Dess- Martin periodinane reagent. Hydrolysis of a 5'-fluoro-5'-S-methyl-5'-thio (α-fluoro thioether) arabinosyl derivative also gave the 5'-carboxaldehyde. Treatment of 5'-carboxaldehydes with hydroxylamine [or O-(methyl, ethyl, and benzyl)hydroxylamine] hydrochloride gave E/Z oximes. Treatment of purified oximes with aqueous trifluoroacetic acid and acetone effected trans-oximation to provide clean samples of 5'-carboxaldehydes. Adenosine (Ado)-5'- carboxaldehyde and its 4'-epimer are potent inhibitors of S-adenosyl-L- homocysteine (AdoHcy) hydrolase. They bind efficiently to the enzyme and undergo oxidation at C3' to give 3'-keto analogues with concomitant reduction of the NAD+ cofactor to give an inactive, tightly bound NADH-enzyme complex (type I cofactor-depletion inhibition). Potent type I inhibition was observed with 5'-carboxaldehydes that contain a ribo cis-2',3'-glycol. Their oxime derivatives are 'proinhibitors' that undergo enzyme-catalyzed hydrolysis to release the inhibitors at the active site. The 2'-deoxy and 2'-epimeric (arabinosyl) analogues were much weaker inhibitors, and the 3'-deoxy compounds bind very weakly. Ado-5'-carboxaldehyde oxime had potent cytotoxicity in tumor cell lines and was toxic to normal human cells. Analogues had weaker cytotoxic and antiviral potencies, and the 3'-deoxy compounds were essentially devoid of cytotoxic and antiviral activity.