2'-Deoxyadenosine

Base Information

• Chemical Name: 2'-Deoxyadenosine
• CAS No.: 958-09-8
• Deprecated CAS: 7005-15-4,663188-78-1,96893-70-8
• Molecular Formula: C10H13N5O3
• Molecular Weight: 251.245
• Hs Code.: 2934999090
• European Community (EC) Number: 213-488-7,683-408-7
• UNII: P582C98ULC
• DSSTox Substance ID: DTXSID10883624
• Nikkaji Number: J80.042B
• Wikipedia: Deoxyadenosine
• Wikidata: Q422457
• NCI Thesaurus Code: C1503
• Metabolomics Workbench ID: 37076
• ChEMBL ID: CHEMBL449329
• Mol file: 958-09-8.mol

Synonyms:2'-deoxyadenosine;2-deoxyadenosine;deoxyadenosine

Chemical Property of 2'-Deoxyadenosine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 187-189 °C
• Refractive Index: 1.7610 (estimate)
• Boiling Point: 627.2 °C at 760 mmHg
• PKA: pK1:3.8(+1) (25°C,μ=0.1)
• Flash Point: 333.1 °C
• PSA: 119.31000
• Density: 1.91 g/cm³
• LogP: -0.36960
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: Soluble in water and caustic soda.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 251.10183929
• Heavy Atom Count: 18
• Complexity: 307

Purity/Quality:

98% ^*data from raw suppliers

2’-Deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O
• Description: 2'-Deoxyadenosine is a natural deoxyribonucleoside, which is a structural fragment of deoxyribonucleic acid DNA. It is a purine nucleoside component of DNA comprised of adenosine linked by its N9 nitrogen to the C1 carbon of deoxyribose. Like other natural nucleosides, it is involved in the transmission of genetic information in almost all biological cells, affecting protein synthesis and polysaccharide. It plays a very important role in regulating the growth, proliferation, differentiation and inhibition of cells in vivo.
• Uses: 2'-Deoxyadenosine is used in paradoxical stimulation study of human sperm motility. It plays an essential role as sperm motility stimulants used in sperm micro-injection on mouse and human embryo development. It finds an application in some cells as an energy source under energy stress conditions. It is involved in various biological processes to compare the functions of adenosine analogues.

Technology Process of 2'-Deoxyadenosine

There total 167 articles about 2'-Deoxyadenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + 7-methyl-2′-deoxyguanosine hydroiodide → 7-methylguanine (578-76-7) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

With potassium dihydrogenphosphate; purine nucleoside phosphatase; In water; at 45 ℃; for 16h; enzymatic synthesis of various β-D-ribo (and desoxyribo) nucleoside analogs; effect of temperature: 25-60 deg C;

DOI:10.1002/hlca.19930760520

Reference yield:

5'-d(AGTAT[5-ethynyl-U]GACCTA)-3' → 2'-deoxycytidine (959326-89-7) + 2'-Deoxyguanosine (961-07-9) + 2'-deoxy-5-ethynyluridine (61135-33-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

With tris hydrochloride; alkaline phosphatase; snake venom phosphodiesterase; at 37 ℃; pH=8.3; Enzymatic reaction;

DOI:10.1002/chem.201001572

Reference yield:

N6-[benzaldehyde hydrazone]-2'-deoxyadenosine (1203661-20-4) → benzaldehyde (100-52-7) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

With GLUTATHIONE; water; Quantum yield; Photolysis; aq. phosphate buffer; UV-irradiation; Inert atmosphere;

DOI:10.1021/tx900268r

upstream raw materials:

(1R)-S-ethyl-1-(6-amino-purin-9-yl)-1,4-anhydro-2-thio-D-arabitol

2'-deoxyadenosine 3'-monophosphate

2'-deoxyuridine

7H-purin-6-ylamine

Downstream raw materials:

(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-{6-[1-methyl-pyrrolidin-(2E)-ylideneamino]-purin-9-yl}-tetrahydro-furan-3-ol

7-(7-Methyl-benzo[a]anthracen-12-ylmethyl)-7H-purin-6-ylamine

3-(12-Methyl-benzo[a]anthracen-7-ylmethyl)-3H-purin-6-ylamine

(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Refernces

• 1、 Annunziata, Francesca,Bavaro, Teodora,Calleri, Enrica,Conti, Paola,Pinto, Andrea,Previtali, Clelia,Rinaldi, Francesca,Speranza, Giovanna,Tamborini, Lucia,Terreni, Marco,Ubiali, Daniela. "An enzymatic flow-based preparative route to vidarabine". . . Retrieved 2020/03/23.
• 2、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". . p. 867 - 876. Retrieved 2020/01/24.