N-Methyl-L-methionine

Base Information

• Chemical Name: N-Methyl-L-methionine
• CAS No.: 42537-72-4
• Molecular Formula: C6H13NO2S
• Molecular Weight: 163.241
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID20195326
• Nikkaji Number: J367.733H
• Wikidata: Q27104522
• Metabolomics Workbench ID: 52357
• ChEMBL ID: CHEMBL48185
• Mol file: 42537-72-4.mol

Synonyms:N-Methyl-L-methionine;42537-72-4;H-N-Me-Met-OH;L-Methionine, N-methyl-;N-methylmethionine;N-Methyl Methionine;N-Me-Met;N-Me-Met-OH;N-Me-L-Met;N-Me-L-Met-OH;(2S)-2-(methylamino)-4-methylsulfanylbutanoic acid;CHEBI:44003;(2S)-2-(methylamino)-4-(methylsulfanyl)butanoic acid;SCHEMBL76427;CHEMBL48185;DTXSID20195326;YAXAFCHJCYILRU-YFKPBYRVSA-N;AM9321;MFCD18070893;F79036;Q27104522

Chemical Property of N-Methyl-L-methionine

Chemical Property:

• Vapor Pressure: 0.000227mmHg at 25°C
• Melting Point: 255-257 °C
• Boiling Point: 302.7°C at 760 mmHg
• PKA: 2.25±0.10(Predicted)
• Flash Point: 136.8°C
• PSA: 74.63000
• Density: 1.122g/cm³
• LogP: 0.80300
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 163.06669983
• Heavy Atom Count: 10
• Complexity: 108

Purity/Quality:

98.5% ^*data from raw suppliers

H-N-Me-Met-OH 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(CCSC)C(=O)O
• Isomeric SMILES: CN[C@@H](CCSC)C(=O)O

Technology Process of N-Methyl-L-methionine

There total 9 articles about N-Methyl-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: 75.0%

(4S)-N-tert-butyloxycarbonyl-4-(2-methylthioethyl)-1,3-oxazolidin-5-one (225386-53-8) → N-methyl-L-methionine (42537-72-4,526210-74-2)

Guidance literature:

With N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h;

Reference yield:

androsamide → L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + N-methyl-4-methoxy-L-tryptophan + N-methyl-L-methionine (42537-72-4,526210-74-2)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 0.5h;

DOI:10.1021/acs.jnatprod.0c00815

Reference yield:

4-methylthio-2-oxobutanoic acid (583-92-6) + methylamine (74-89-5) → N-methyl-L-methionine (42537-72-4,526210-74-2)

Guidance literature:

With D-Glucose; Bacillus megaterium glucose dehydrogenase; ammonia; Symbiobacterium thermophilum mesodiaminopimelate dehydrogenase; Enzymatic reaction;

DOI:10.1021/acscatal.0c01895

upstream raw materials:

(S)-2-bromo-4-methylsulfanyl-butyric acid

methylamine

N-methyl-D-methionine

S-benzyl-N-methyl-homocysteine

Downstream raw materials:

N-methyl-DL-methionine

N-Methyl-S-(4,4'-dimethoxy-trityl)-L-homocysteine

N-methyl-S-trityl-L-homocysteine

Refernces

• 1、 Lee, Jihye,Gamage, Chathurika. D. B.,Kim, Geum Jin,Hillman, Prima F.,Lee, Chaeyoung,Lee, Eun Young,Choi, Hyukjae,Kim, Hangun,Nam, Sang-Jip,Fenical, William. "Androsamide, a Cyclic Tetrapeptide from a Marine Nocardiopsis sp., Suppresses Motility of Colorectal Cancer Cells". . p. 3166 - 3172. Retrieved 2020/11/02.
• 2、 -. "Orthogonally protected bifunctional amino acid". Page/Page column title page; 19; 34. . Retrieved 2010/11/24.