S-adenosyl-L-methionine

Base Information

• Chemical Name: S-adenosyl-L-methionine
• CAS No.: 485-80-3
• Deprecated CAS: 15648-75-6,55722-10-6,93240-48-3
• Molecular Formula: C₁₅H₂₃N₆O₅S
• Molecular Weight: 399.451
• DSSTox Substance ID: DTXSID20110014
• Nikkaji Number: J23.293I,J260.469H
• Wikipedia: S-Adenosyl_methionine
• Wikidata: Q56071634,Q27115647,Q27115649
• NCI Thesaurus Code: C100098,C63661
• RXCUI: 9504
• Metabolomics Workbench ID: 37647
• ChEMBL ID: CHEMBL224120
• Mol file: 485-80-3.mol

Synonyms:Ademetionine;AdoMet;FO 1561;FO-1561;FO1561;Gumbaral;S Adenosyl L Methionine;S Adenosylmethionine;S Adenosylmethionine Sulfate Tosylate;S Amet;S-Adenosyl-L-Methionine;S-Adenosylmethionine;S-Adenosylmethionine Sulfate Tosylate;SAM-e;Samyr

Chemical Property of S-adenosyl-L-methionine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 207.93000
• Density: g/cm³
• LogP: -0.64070
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 399.14506403
• Heavy Atom Count: 27
• Complexity: 533

Purity/Quality:

99%, ^*data from raw suppliers

S-adenosylmethionine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[S+](CCC(C(=O)O)N)CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Recent ClinicalTrials: S-Asenosyl-L-Methionine vs Placebo for Osteoarthritis of the Hands
• Recent EU Clinical Trials: SAMe as an epigenetic treatment of depression in people with childhood trauma, a double blind placebo-controlled trial

Technology Process of S-adenosyl-L-methionine

There total 7 articles about S-adenosyl-L-methionine 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:

L-methionine (63-68-3,26062-47-5,58576-49-1) + 5'-deoxy-5'-chloroadenosine (892-48-8) → S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6)

Guidance literature:

With Sterptomyces cattleya fluorinase; In phosphate buffer; at 37 ℃; for 12h; pH=7.8;

DOI:10.1002/anie.200503582

Reference yield:

adenosine 5'-triphosphate + [methyl-13C]-L-methionine (49705-26-2) → S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6)

Guidance literature:

With E_. coli methionine adenosyltransferase; potassium chloride; magnesium chloride; In aq. phosphate buffer; at 37 ℃; for 1h; pH=8; Enzymatic reaction;

DOI:10.1021/ol501241a

Reference yield:

methyl bromide (74-83-9) + S-(5'-adenosyl)-L-homocysteine (979-92-0) → S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6)

Guidance literature:

With formic acid; silver trifluoromethanesulfonate; at 20 ℃; for 24h;

DOI:10.1002/anie.200905095

upstream raw materials:

L-methionine

5’-fluoro-5’-deoxyadenosine

5'-deoxy-5'-chloroadenosine

methyl bromide

Downstream raw materials:

4'-O-methylepigallocatechin

isoformononetin

daidzein

7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

Refernces

• 1、 Lowe, Phillip T.,Cobb, Steven L.,O'Hagan, David. "An enzymatic Finkelstein reaction: Fluorinase catalyses direct halogen exchange". supporting information. p. 7493 - 7496. Retrieved 2019/08/20.
• 2、 Sadler, Joanna C.,Humphreys, Luke D.,Snajdrova, Radka,Burley, Glenn A.. "A Tandem Enzymatic sp2-C-Methylation Process: Coupling in Situ S-Adenosyl-l-Methionine Formation with Methyl Transfer". . p. 992 - 995. Retrieved 2017/06/13.