4097-22-7

Usage

Uses

Used in Pharmaceutical Industry:
Dideoxyadenosine is used as a potent anti-HIV agent for its ability to inhibit the replication of the human immunodeficiency virus (HIV). It plays a crucial role in the treatment and management of HIV/AIDS by helping to control the viral load and prevent the progression of the disease.
Used in Research and Development:
Dideoxyadenosine is used as a specific adenylyl cyclase inhibitor in biological process and pathway studies involving adenylyl cyclase activity and cAMP pool modulation. This application is essential for understanding the role of adenylyl cyclase in various cellular processes and its potential as a therapeutic target for various diseases.
Used in Diagnostics:
As a potent labeled anti-HIV agent, Dideoxyadenosine can be utilized in the development of diagnostic tools and tests for the detection and monitoring of HIV infection. This application aids in the early identification of the virus and the implementation of appropriate treatment strategies.

Air & Water Reactions

Water soluble.

Reactivity Profile

Dideoxyadenosine may be sensitive to prolonged exposure to light.

Health Hazard

SYMPTOMS: Symptoms of exposure to a related compound include cutaneous eruptions, fever, mouth sores, thrombocytopenia, neutropenia, reversible peripheral neuropathy, gastrointestinal distress, headache, nausea and vomiting.

Fire Hazard

Flash point data for Dideoxyadenosine are not available; however, Dideoxyadenosine is probably combustible.

Upstream product

• 7057-48-9 2',3'-didehydro-2',3'-dideoxyadenosine 
• 37818-74-9 [5-(6-amino-purin-9-yl)-4,5-dihydro-furan-2-yl]-methanol 
• 117174-29-5 Benzoic acid (S)-5-(6-amino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester 
• 4097-22-7 [(S)-5-(6-Amino-purin-9-yl)-tetrahydro-furan-2-yl]-methanol 
• 145177-24-8 2,2-Dimethyl-propionic acid (2S,5R)-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester 
• 128075-93-4 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine 
• 42867-78-7 9-(2'-O-Acetyl-3'-bromo-3'-deoxy-β-D-xylofuranosyl)adenine 
• 37731-72-9 9-(2-O-acetyl-3-bromo-3-deoxy-5-O-(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl)adenine 
• 62805-48-5 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-1,9-dihydro-6H-purine-6-one 
• 66224-66-6 adenine 
• 5983-09-5 2',3'-Dideoxyuridine 
• 73-03-0 cordycepin 
• 862179-59-7 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-adenosine 
• 90362-50-8 5'-O-benzoyl-2'-deoxyadenosine 

Downstream Products

• 139300-69-9 Oxalic acid (2S,5R)-5-(6-amino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester 4-nitro-phenyl ester 
• 121353-86-4 8-bromo-2',3'-dideoxyadenosine 
• 69655-05-6 Dideoxyinosine 
• 287198-64-5 {9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-carbamic acid phenyl ester 
• 129533-46-6 [9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-carbamic acid benzyl ester 
• 181479-31-2 (9-{(2R,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid benzyl ester 
• 129533-29-5 2,2-Dimethyl-propionic acid (2S,5R)-5-(6-benzyloxycarbonylamino-purin-9-yl)-tetrahydro-furan-2-ylmethoxymethyl ester 
• 181479-34-5 Hexadecanoic acid (2S,5R)-5-(6-benzyloxycarbonylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester 
• 73-24-5 adenine 
• 85326-06-3 2',3'-dideoxyguanosine 
• 107550-73-2 2,6-diaminopurine 2',3'-dideoxyriboside 

Relevant academic research and scientific papers

A MILD CONVERSION OF VICINAL DIOLS TO ALKENES. EFFICIENT TRANSFORMATION OF RIBONUCLEOSIDES INTO 2'-ENE AND 2',3'-DIDEOXYNUCLEOSIDES

α-Acetoxyisobutyryl bromide in "moist" acetonitrile converted adenosine to trans-3'(2')-bromo-2'(3')-acetates with 3percent glycosyl cleavage.This mixture was acetylated, treated with Zn/Cu/DMF, and deacylated to give 81percent of the 2'-alkene.

An effective and convenient synthesis of cordycepin from adenosine

Cordycepin is a purine nucleoside analog with potent and diverse biological activities. Herein, we designed two methods to synthesize cordycepin. One method mainly converted the 3′-OH group into an iodide group and further dehalogenation to yield the final product. Although this method presented a short synthetic procedure, the synthesis had a low overall yield, resulting in only 13.5% overall yield. To improve the overall yield of cordycepin, another synthetic route was studied, which consisted of four individual steps: (1) 5′-OH protection (2) esterification (3) -O-tosyl (-OTs) group removal (4) deprotection. The key step in the synthetic method involved the conversion of 5′-O-triphenylmethyladenosine to 3′-O-tosyl-5′-O-triphenylmethyladenosine, using LiAlH4 as reducing agent. The main advantages of this route were an acceptable total product yield and the commercial availability of all starting materials. The optimal reaction conditions for each step of the route were identified. The overall yield of cordycepin obtained from adenosine as the starting material was 36%.

A stent green synthesis method (by machine translation)

The invention discloses a stent green synthesis method. The invention to a wide variety of sources adenosine as the starting material, passes through the cyclization, open-loop, catalytic hydrogenation - alkaline hydrolysis, adopts the steps are less, the obtained few by-products, and improves the yield, and reduces the production cost. (by machine translation)

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.

An acyl-SAM analog as an affinity ligand for identifying quorum sensing signal synthases

N-Acylhomoserine lactones (AHLs) are quorum sensing signals produced by Gram-negative bacteria. We here report the affinity purification of AHL synthases using beads conjugated with an enzyme inhibitor, which was designed based on the catalytic intermediate acyl-SAM. the Partner Organisations 2014.

Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A new photochemical flow reactor has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly improved both the efficiency and selectivity of the reaction, with the streamlined multi-step sequence directly furnishing the highly desired unprotected deoxynucleosides.

Continuous flow photocatalysis enhanced using an aluminum mirror: Rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A unique photochemical flow reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.

Aeromonas hydrophila strains as biocatalysts for transglycosylation

Microbial transglycosylation is useful as a green alternative in the preparation of purine nucleosides and analogues, especially for those that display pharmacological activities. In a search for new transglycosylation biocatalysts, two Aeromonas hydrophila strains were selected. The substrate specificity of both micro-organisms was studied and, as a result, several nucleoside analogues have been prepared. Among them, ribavirin, a broad spectrum antiviral, and the well-known anti HIV didanosine, were prepared, in 77 and 62% yield using A. hydrophila CECT 4226 and A. hydrophila CECT 4221, respectively. In order to scale-up the processes, the reaction conditions, product purification and biocatalyst preparation were analyzed and optimized.

METHOD FOR PRODUCING NUCLEOSIDE DERIVATIVE

The present invention relates to a method for producing a nucleoside derivative represented by formula (2), comprising the step of reducing a nucleoside of formula (1) in the presence of a noble metal catalyst comprising a carrier and a noble metal supported thereby, selected from the group consisting of (A) a homogeneously supported catalyst where the specific surface area of the noble metal is 95.0 m2/g or more and the particle size of the noble metal is 4.3 nm or less, and (B) a surface-loaded catalyst where the specific surface area of the noble metal is 56.0 m2/g or more and the particle size of the noble metal is 8.0 nm or less, wherein R1 is hydrogen or a protective group, R2 is NH2 or OH, R3 is an acyl group, and X is a chlorine or bromine atom. According to the present invention, the yield can be made equal even when the amount of catalyst is smaller than that used for the conventional products.

Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases

2′-Deoxy, 3′-deoxy, and 2′,3′-dideoxyribosyl surrogates of isoleucyl and methionyl sulfamate adenylates have been investigated to identify the pharmacophoric importance of the ribose group for the inhibition of Escherichia coli methionyl-tRNA (MRS) and isoleucyl-tRNA (IRS) synthetases. Molecular modeling of 2′,3′-dideoxyribosyl Met-NHSO2-AMP (9) with the crystal structure of E. coli MRS revealed that the lack of the two hydroxyl groups on ribose was compensated by the formation of an extra hydrogen bond between the ring oxygen and His24, resulting in a small activity reduction.