5'-Deoxyadenosine

Base Information

• Chemical Name: 5'-Deoxyadenosine
• CAS No.: 4754-39-6
• Molecular Formula: C10H13 N5 O3
• Molecular Weight: 251.245
• UNII: 2U0TYC8Y5A
• DSSTox Substance ID: DTXSID901036031
• Nikkaji Number: J103.510J
• Wikidata: Q27102319
• Metabolomics Workbench ID: 37963
• ChEMBL ID: CHEMBL443485
• Mol file: 4754-39-6.mol

Synonyms:5'-dAdo nucleoside;5'-deoxyadenosine

Chemical Property of 5'-Deoxyadenosine

Chemical Property:

• Vapor Pressure: 5.29E-15mmHg at 25°C
• Boiling Point: 595°Cat760mmHg
• PKA: 13.29±0.70(Predicted)
• Flash Point: 313.6°C
• PSA: 119.31000
• Density: 1.93g/cm³
• LogP: -0.37120
• Storage Temp.: 2-8°C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 251.10183929
• Heavy Atom Count: 18
• Complexity: 320

Purity/Quality:

98%,99%, ^*data from raw suppliers

5''-Deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Description: 5'-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. Oxidized nucleosides represent excellent biomarkers for determining the extent of damage in genetic material, which has long been of interest in understanding the mechanism of aging, neurodegenerative diseases, and carcinogenesis.
• Uses: 5′-Deoxyadenosine has been used:as a standard in mass spectroscopyas an inhibitor for screening thymidine phosphorylase activityas a substrate in 5′-Deoxyadenosine deaminase (DadD) assay

Technology Process of 5'-Deoxyadenosine

There total 54 articles about 5'-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: 100.0%

adenosylcobalamin → 8,5'-Anhydroadenosine (3415-89-2) + cob(II)alamin + 5'-deoxyadenosine (4754-39-6)

Guidance literature:

With d4-ethylene glycol; In further solvent(s); N2, 110.0°C, solvent: d-ethylene glycol, main product is 8,5`-anhydroadenosine (>78%);; not isolated, identified by 1H NMR spectroscopy;; Kinetics;

DOI:10.1016/S0277-5387(00)81775-1

Reference yield: 99.0%

5'-iodo-5'-deoxyadenosine (4099-81-4) → 5'-deoxyadenosine (4754-39-6)

Guidance literature:

With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol; In water; at 100 ℃; for 4h;

DOI:10.1021/ol7020803

Reference yield: 93.0%

5'-deoxy-5'-chloroadenosine (892-48-8) → 5'-deoxyadenosine (4754-39-6)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; dimethyl sulfoxide; Ambient temperature;

DOI:10.1139/v91-217

upstream raw materials:

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose

6-benzamido-9-(chloromercuri)purine

5'-Deoxy-5'-methylthioadenosine

3',5'-di-O-p-tolylsulphonyladenosine

Downstream raw materials:

2-amino-9-(5-deoxy-β-D-ribofuranosyl)-9H-6-thiopurine

adenine

C₃₈H₂₉N₅O₇

1-(3-methyl-2-butenylamino)-9-(5'-deoxy-β-D-ribofuranosyl)purine hydrobromide

Refernces

• 1、 Echavarri-Erasun, Carlos,Fajardo, Ana Sosa,Legrand, Pierre,Martin, Lydie,Nicolet, Yvain,Payá-Tormo, Luc?a,Pellicer Mart?nez, Maria Teresa,Rubio, Luis M.,Vernède, Xavier. "Structural Insights into the Mechanism of the Radical SAM Carbide Synthase NifB, a Key Nitrogenase Cofactor Maturating Enzyme". . p. 11006 - 11012. Retrieved 2020.
• 2、 Mehta, Angad P.,Hanes, Jeremiah W.,Abdelwahed, Sameh H.,Hilmey, David G.,H?nzelmann, Petra,Begley, Tadhg P.. "Catalysis of a new ribose carbon-insertion reaction by the molybdenum cofactor biosynthetic enzyme MoaA". . p. 1134 - 1136. Retrieved 2013.
• 3、 Chen, Ridao,Feng, Jianqiang,Gao, Jin-Ming,Hou, Xueli,Lee, Yu-Hsuan,Liu, Hung-Wen,Liu, Xiao,Ruszczycky, Mark W.,Wang, Binju,Zhou, Jiahai. "Radical S-Adenosyl Methionine Enzyme BlsE Catalyzes a Radical-Mediated 1,2-Diol Dehydration during the Biosynthesis of Blasticidin S". supporting information. p. 4478 - 4486. Retrieved 2022/03/18.