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Usage

Uses

Used in Pharmaceutical Industry:
2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol is used as an active pharmaceutical ingredient for the development of drugs targeting various diseases. Its unique structure allows it to interact with specific biological targets, making it a promising candidate for drug discovery and development.
Used in Research and Development:
In the field of research and development, 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol is used as a key compound for studying the structure and function of nucleic acids and their interactions with proteins. This understanding can lead to the development of novel therapeutic strategies for various diseases.
Used in Diagnostic Applications:
2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol can be employed as a diagnostic marker or probe in the detection and monitoring of certain diseases. Its specific interactions with biological targets can be exploited to develop sensitive and selective diagnostic assays.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol can be used as a starting material or intermediate for the synthesis of more complex molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Cosmetics Industry:
2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol may also find applications in the cosmetics industry, where it could be used as an active ingredient in skincare products due to its potential beneficial effects on skin health and its ability to interact with biological targets relevant to skin biology.

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

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

Downstream Products

• 31079-96-6 O-monomethoxytrityl-5' β-D-xylofurannosyl-9 adenine 
• 532-20-7 D-xylofuranose 
• 66224-66-6 adenine 
• 15830-78-1 8-bromo-9-(β-D-xylofuranosyl)adenine 
• 70147-59-0 1-(6-amino-purin-9-yl)-5-chloro-β-D-1,5-dideoxy-xylofuranose 
• 203584-03-6 (2R,3R,4R,5S)-2-(6-Amino-purin-9-yl)-5-(4-methoxy-phenylsulfanylmethyl)-tetrahydro-furan-3,4-diol 
• 203584-05-8 3'-deoxy-3'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine 
• 203584-06-9 (2R,3S,4S,5R)-2-(6-Amino-purin-9-yl)-4-chloro-5-(4-methoxy-phenylsulfanylmethyl)-tetrahydro-furan-3-ol 
• 203584-08-1 2'-O-acetyl-3'-deoxy-3'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine 
• 203584-09-2 2'-O-acetyl-3'-chloro-3'-deoxy-5'-S-(4-methoxyphenyl)-5'-thioadenosine 
• 83649-44-9 (S)-2-Amino-3-phenyl-propionic acid (2R,3R,4S,5R)-2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester 
• 83649-43-8 2'-O--9-β-D-xylofuranosyladenine 
• 83649-49-4 9-<2-O--3,5-O-isopropylidene-β-D-xylofuranosyl>adenine 
• 116143-53-4 endo-2',3'-O-decylideneadenosine 

Relevant academic research and scientific papers

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.

Studies on the mechanism of ribonucleotide reductases

Ribonucleotide reductases are enzymes that catalyze the conversion of ribonucleotides to 2'-deoxyribonucleotides. This important reaction is initiated by the generation of a C-3' nucleotide radical and subsequent loss of the 2'-hydroxyl group. In order to model certain steps in this mechanism, selenol ester 23 was prepared and photolyzed providing the first selective chemical access to the 3'-adenosyl radical. From product analysis it could be shown that elimination of the 2'-OH function readily takes place under general base catalysis. The rate coefficient for this reaction was determined by competition kinetics to be 1.5 · 106 s-1 in the presence of 1 M triethylammonium acetate buffer at pH 7. Without catalyst the elimination rate is about 103 times slower. It can be concluded that a similar mechanism is also feasible for the key steps of the enzyme catalyzed reaction.

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.

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.

Photochemical Reactions of Triplet Acetone with Indole, Purine, and Pyrimidine Derivatives

The photochemical reactions of triplet acetone with indole, indole derivatives (1-methyl-, 2-methyl-, 3-methyl-, 5-methyl-, and 7-methylindole, and tryptophan), purine derivatives (caffeine, 7-methylguanine, adenine, adenosine, and guanosine), and a pyrimidine derivative (thymine) have been studied in aqueous solutions by using a KrF or ArF laser.The quenching processes of triplet acetone by indoles, being diffusion controlled, occur via the following paths: triplet-triplet energy transfer, electron transfer, photoaddition of triplet acetone to the 2-carbon atom of the indole ring, and deactivation without a chemical change.The yields of energy transfer, electron transfer, and photoaddition were determined from absorbance measurements.The transient absorptions due to triplet states were observed for caffeine, 7-methylguanine, and thymine, while weak transient absorptions which showed apparent second-order decays were observed for adenine, adenosine, and guanosine.Triplet acetone is quenched mainly via T-T energy transfer in caffeine, 7-methylguanine, and thymine.The weak absorptions may be attributed to neutral radicals in adenine and adenosine and to a cation radical in guanosine.