5'-Deoxy-5'-methylthioadenosine

Base Information

• Chemical Name: 5'-Deoxy-5'-methylthioadenosine
• CAS No.: 2457-80-9
• Deprecated CAS: 37311-40-3
• Molecular Formula: C11H15 N5 O3 S
• Molecular Weight: 297.338
• Hs Code.: 2934999090
• European Community (EC) Number: 626-314-3
• UNII: 634Z2VK3UQ
• DSSTox Substance ID: DTXSID20179308
• Nikkaji Number: J419.054H
• Wikipedia: 5%E2%80%B2-Methylthioadenosine
• Wikidata: Q3599216
• Metabolomics Workbench ID: 37638
• ChEMBL ID: CHEMBL277041
• Mol file: 2457-80-9.mol

Synonyms:5'-deoxy-5'-(methylthio)adenosine;5'-deoxy-5'-methylthioadenosine;5'-methylthio-5'-deoxyadenosine;5'-methylthioadenosine;5'-methylthioadenosine, methyl-(14)C-labeled;5-MTDA;adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoriboside

Chemical Property of 5'-Deoxy-5'-methylthioadenosine

Chemical Property:

• Melting Point: 210-213 °C (dec.)
• Boiling Point: 642.7°Cat760mmHg
• PKA: 13.10±0.70(Predicted)
• Flash Point: 342.5°C
• PSA: 144.61000
• Density: 1.85g/cm³
• LogP: -0.02810
• Storage Temp.: −20°C
• Solubility.: DMF (Sparingly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 297.08956053
• Heavy Atom Count: 20
• Complexity: 352

Purity/Quality:

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

5?-Deoxy-5?-methylthioadenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: CSC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Recent ClinicalTrials: Clinical and Radiographic Evaluation of Laser Photobiomodulation Pulpotomy of Primary Molars in Children
• Uses: 5′-Deoxy-5′-(methylthio)adenosine has been used as a protein methylation inhibitor to reduce E2F transcription factor 1 (E2F1) protein abundance in hepatocellular carcinoma (HCC) cells. It has also been used to inhibit histone methylation modification and study its role in hypoxia inducible factor-1 (Hif-1) nuclear transport.

Technology Process of 5'-Deoxy-5'-methylthioadenosine

There total 24 articles about 5'-Deoxy-5'-methylthioadenosine 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: 86.0%

methylthiol (74-93-1) + 5'-deoxy-5'-chloroadenosine (892-48-8) → 5'-Deoxy-5'-methylthioadenosine (2457-80-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; -30 deg C to r.t., overnight;

DOI:10.1139/v91-217

Reference yield: 65.0%

5'-deoxy-5'-chloroadenosine (892-48-8) + sodium thiomethoxide (5188-07-8) → 5'-Deoxy-5'-methylthioadenosine (2457-80-9)

Guidance literature:

In water; at 75 ℃; for 24h;

DOI:10.1002/anie.201609948

Reference yield: 38.0%

Dimethyldisulphide (624-92-0) + adenosine (58-61-7) → 5'-Deoxy-5'-methylthioadenosine (2457-80-9)

Guidance literature:

With tributylphosphine; In N,N-dimethyl-formamide; for 240h;

upstream raw materials:

9-((3aR,4R,6S,6aS)-2,2-dimethyl-6-((methylthio)methyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

2',3'-Di-O-acetyl-5'-deoxy-5'-(methylthio)adenosine sulfoxide

methylthiol

5'-deoxy-5'-chloroadenosine

Downstream raw materials:

adenine

7H-purin-6-ylamine

N⁶,N⁶-dibenzoyl-2',3'-O-dibenzoyl-5'-deoxy-5'-fluoromethylthioadenosine

Refernces

• 1、 Parks,Schlenk. "-". . p. 291. Retrieved 1958.
• 2、 Wang, Rui,Zheng, Weihong,Luo, Minkui. "A sensitive mass spectrum assay to characterize engineered methionine adenosyltransferases with S-alkyl methionine analogues as substrates". . p. 11 - 19. Retrieved 2014.
• 3、 -. "SELECTIVE INHIBITORS OF PROTEIN ARGININE METHYLTRANSFERASE 5 (PRMT5)". Paragraph 00168. . Retrieved 2018/01/20.