3228-71-5

Basic information

• Product Name: 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 9-α-D-Arabinofuranosyl-9H-purin-6-amine;9-alpha-D-Arabinofuranosyladenine;9H-Purin-6-amine, 9-alpha-D-arabinofuranosyl- (9ci);Adenine, 9-alpha-D-arabinofuranosyl- (8ci);alpha-D-Arabinofuranosyladenine;Nsc 70422
• CAS NO: 3228-71-5
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.24
• Mol File: 3228-71-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 676.3°C at 760 mmHg
• Flash Point: 362.8°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 3.26E-19mmHg at 25°C
• Refractive Index: 1.907
• 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(3228-71-5)
• EPA Substance Registry System: 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol(3228-71-5)

Safety Data

• Hazardous Substances Data: 3228-71-5(Hazardous Substances Data)

Usage

Chemical structure

A complex compound consisting of a purine ring with an amino group at the 6-position and a hydroxymethyl group at the 5-position, attached to an oxolane ring with a diol group at the 3 and 4 positions.

Biological significance

A precursor to the nucleotides that make up DNA and RNA, playing an important role in biological processes.

Pharmaceutical and research applications

Used as a building block for nucleoside analogs and other bioactive compounds in the development of new drugs and scientific studies.

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

• 201677-06-7 9-[2-deoxy-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-1-C-(2,2-dimethyl-1-oxopropoxy)-2-iodo-α-D-ribofuranosyl]-9H-purin-6-amine 
• 58-61-7 adenosine 

Downstream Products

• 98145-34-7 endo-2',3'-O-isobutyleneadenosine 
• 532-20-7 D-arabinofuranose 
• 66224-66-6 adenine 

Relevant articles and documents

Generation of C-1' radicals through a β-(acyloxy)alkyl rearrangement in modified purine and pyrimidine nucleosides

The synthesis of protected 1',2'-didehydro-2'-deoxyadenosines has been optimized by incorporating a phosphoranylidene protection of the adenine amine function. These unsaturated adenosines have served as substrates for the electrophilic iodopivaloyloxylation leading to new nucleosides modified at the anomeric position. Reaction of halopivaloates 10, 11 and 12 with tributyltin hydride generates indirectly C-1' radicals through a β- (acyloxy)alkyl rearrangement. Rate constants for these rearrangements have been measured by using free-radical clock methodology and comparison of these data with previous reported results provides structural information about the nature of this important class of radicals.

Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA 1

The effect of 20-ns pulses of 193-nm laser light on aqueous solutions of purine bases, (2′-deoxy)nucleosides, and (2′-deoxy)nucleotides was investigated, and monophotonic ionization was observed. Although (deoxy)ribose and (deoxy)ribose phosphates are also ionized by 193-nm light, the photoionization of the (deoxy)nucleosides and -tides takes place predominantly (90%) at the purine moiety, due to the much higher extinction coefficients at 193 nm of the bases as compared to the (deoxy)ribose phosphates. The quantum yields of photoionization (φPl) of the purines are in the range 0.01 to 0.08, based on φ(Cl-) at 193 nm of 0.46. As shown by comparison with data obtained from pulse radiolysis, the ionized purines, i.e., the radical cations, deprotonate in neutral solution, yielding neutral radicals. The radical cation of 1-methylguanosine, produced by photoionization in oxygen-saturated aqueous solution, deprotonates with the rate constant 3.5 × 105 s-1. In the absence of oxygen, the hydrated electrons resulting from the photoionization react with the untransformed purine derivatives to yield the corresponding radical anions. As these are rapidly protonated by water (as concluded from pulse radiolysis), the photoionization in deaerated neutral solution results in two different neutral radicals: a deprotonated radical cation and a protonated radical anion.

Preparation of L-beta-ribonucleosides and L-beta-ribonucleotides.

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