524-69-6

Basic information

• Product Name: 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 9-.beta.-D-Xylofuranosyladenine;9H-Purin-6-amine, 9-.beta.-D-xylofuranosyl-;Adenine xyloside;Adenine, 9-.beta.-D-xylofuranosyl-;Nsc 7359;Nsc7359;Xa;Xylosyl a
• CAS NO: 524-69-6
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.24
• Mol File: 524-69-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 125-140 °C
• Boiling Point: 676.3°Cat760mmHg
• Flash Point: 362.8°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 3.26E-19mmHg at 25°C
• Refractive Index: 1.907
• PKA: 13.11±0.70(Predicted)
• CAS DataBase Reference: 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol(524-69-6)
• EPA Substance Registry System: 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol(524-69-6)

Safety Data

• Hazardous Substances Data: 524-69-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A purine nucleoside in which adenine is attached to xylofuranose via a beta-N9-glycosidic bond.

InChI:InChI=1/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6+,7-,10+/m1/s1

Upstream product

• 86734-95-4 9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 634-01-5 adenosine 2',3'-cyclic monophosphate 
• 958-09-8 2'-deoxy-D-adenosine 
• 2627-64-7 9-(2,3-anhydro-β-D-ribofuranosyl)adenine 
• 58-61-7 adenosine 

Downstream Products

• 122336-53-2 (1R)-1-(6-amino-purin-9-yl)-O⁵-trityl-D-1,4-anhydro-xylitol 
• 7687-49-2 9-(3,5-O-isopropylidene-β-D-xylofuranosyl)adenine 
• 13089-44-6 (6aR)-4-amino-8c-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-7c-ol 
• 116143-53-4 endo-2',3'-O-decylideneadenosine 
• 116143-55-6 2',3'-O-(o,o'-biphenylmethylene)adenosine 
• 63248-64-6 1-Ethyladenosine Hydroiodide 
• 116163-47-4 endo-2',3'-O-(tert-butylmethylene)adenosine 
• 98145-34-7 endo-2',3'-O-isobutyleneadenosine 
• 58-61-7 adenosine 
• 31079-96-6 O-monomethoxytrityl-5' β-D-xylofurannosyl-9 adenine 
• 532-20-7 D-xylofuranose 
• 66224-66-6 adenine 
• 16658-10-9 endo-2',3'-O-(methoxymethylene)adenosine 
• 3250-02-0 endo-2',3'-O-(ethoxymethylene)adenosine 

Relevant articles and documents

Generation and Characterization of Psoralen Radical Cations

Radical cations of psoralen, 8-methoxypsoralen (8-MOP) and 5-methoxypsoralen have been generated by photosensitized electron transfer in acetonitrile and aqueous buffer/acetonitrile (1:1) and have absorption maxima at 600, 650 and 550 nm, respectively. The radical cations have lifetimes of ～5 us under these conditions, are unreactive toward oxygen and show behavior typical of arylalkene radical cations in their reactivity toward nucleophiles and the precursor psoralens. Direct 355 nm excitation of 8-MOP in aqueous buffer at physiological pH results in monophotonic photoionization to give 8-MOP.+ with a quantum yield of 0.015. The 8-MOP.+ reacts with both guanosine and adenosine mononucleotides (k = 2.5 × 109 and 3.4 × 107 M-1 s-1, respectively) via electron transfer to give the purine radical cations, but does not react with pyrimidine mononucleotides. These results suggest that reactions of psoralen radical cations generated by electron transfer or photoionization may be involved in psoralen/UVA therapy.

Role of the stereochemistry of 3'-fluoro-3'-deoxy analogues of 2-5A in binding to and activation of mouse RNase L

The synthesis of two sets of analogues of 2-5A trimer containing 9-(3-fluoro-3-deoxy-β-D-xylo-furanosyl)adenine (AF) or 3'-fluoro-3'-deoxyadenosine (AF) at different positions of the chain is described, along with the preparation of the corresponding 5'-monophosphates and 5'-diphosphorylated (core) trimers.The ability of each ribo and xylo isomeric pair of fluorodeoxy analogues of 2-5A (i) to compete with p3(A2'p)3A3'pC3'p for binding to RNase L in L929 cell extracts, and (ii) to activate the partially purified RNase L from L929 cell extracts to hydrolyze poly(U), was compared to that of the related 3'-deoxy analogue and the parent trimer, p3A3, using radiobinding and RNase L-(2',5')pentaadenylate(core)-agarose assays, respectively.Evidence is presented to show that the stereochemistry of the trimers plays an important role, specifically in the second process.The most striking observation is that, compared to 2-5A, p3A(AF)A was found to be nine times more effective an activator of RNase L, whereas isomeric p3A(AF)A is 30 times less effective.

Periodinane oxidation, selective primary deprotection, and remarkably stereoselective reduction of tert-butyldimethylsilyl-protected ribonucleosides. Synthesis of 9-(β-D-xylofuranosyl)adenine or 3'-deuterioadenosine from adenosine

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