Acetyl-L-methionine sulfoxide

Base Information

• Chemical Name: Acetyl-L-methionine sulfoxide
• CAS No.: 108646-71-5
• Molecular Formula: C7H13 N O4 S
• Molecular Weight: 207.251
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID60428600
• Nikkaji Number: J2.514.637I,J700.323D
• ChEMBL ID: CHEMBL1221835
• Mol file: 108646-71-5.mol

Synonyms:AC-MET(O)-OH;108646-71-5;Acetyl-L-methionine sulfoxide;(2S)-2-acetamido-4-methylsulfinylbutanoic acid;N-Acetylmethionine oxide;(2S)-2-ACETAMIDO-4-METHANESULFINYLBUTANOIC ACID;N-Acetylmethionine S-oxide;Ac-Met(O)-OH, AldrichCPR;SCHEMBL1129578;CHEMBL1221835;DTXSID60428600;MFCD00236766;AKOS015909360;AS-46801;CS-0208763;F10544;EN300-7361005;(2S)-2-(Acetylamino)-4-(methylsulfinyl)butanoic acid;Butanoic acid,2-(acetylamino)-4-(methylsulfinyl)-,(2S)-

Chemical Property of Acetyl-L-methionine sulfoxide

Chemical Property:

• Melting Point: 181-183 °C
• Boiling Point: 587.3±45.0 °C(Predicted)
• PKA: 3.41±0.10(Predicted)
• PSA: 102.68000
• Density: 1.341±0.06 g/cm3(Predicted)
• LogP: 0.60090
• Storage Temp.: 2-8°C
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 207.05652907
• Heavy Atom Count: 13
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

Acetyl-L-methionine sulfoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CCS(=O)C)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CCS(=O)C)C(=O)O
• Uses: (2S)-2-(Acetylamino)-4-(methylsulfinyl)butanoic Acid is used as an analyte in the biological study of monitoring methionine sulfoxide with stereospecific mechanism-based fluorescent sensors.

Technology Process of Acetyl-L-methionine sulfoxide

There total 8 articles about Acetyl-L-methionine sulfoxide 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: 80.0%

N-acetyl-l-methionine (65-82-7) → (2S)-2-(acetylamino)-4-(methylsulfinyl)butyric acid (108646-71-5)

Guidance literature:

With oxygen; In water; acetonitrile; at 23 - 27 ℃; for 0.333333h; chemoselective reaction; Irradiation; Green chemistry;

DOI:10.1002/adsc.201501123

Reference yield: 70.0%

L-methionine sulfoxide (3226-65-1,86631-49-4,779988-65-7) + acetic anhydride (108-24-7) → (2S)-2-(acetylamino)-4-(methylsulfinyl)butyric acid (108646-71-5)

Guidance literature:

In acetic acid; at 10 ℃; for 6h;

DOI:10.1039/c39860001810

Reference yield: 50.0%

N-acetyl-DL-methionine (1115-47-5) → N-Acetyl-DL-β-methionin-sulfoxid (108646-71-5,114714-85-1,3054-51-1)

Guidance literature:

With oxygen; t2H)(μ-PBu^t2)>2; In tetrahydrofuran; at 50 ℃; for 48h; under 760 Torr;

DOI:10.1021/jo00131a009

upstream raw materials:

N-acetyl-DL-methionine

N-acetyl-l-methionine

L-methionine sulfoxide

acetic anhydride

Downstream raw materials:

L-methionine sulfoxide

Refernces

• 1、 Schue, Léonard,Jean-Baptiste, Pierre-Michel,Du, Yunyun,Jintoku, Hirokuni,Ihara, Hirotaka,Oda, Reiko,Nlate, Sylvain. "Electrostatic immobilization of substrate and polyoxotungstate catalyst at the surface of micelles for enhanced reaction efficiency in water". . p. 65 - 68. Retrieved 2015.
• 2、 Gennaris, Alexandra,Ezraty, Benjamin,Henry, Camille,Agrebi, Rym,Vergnes, Alexandra,Oheix, Emmanuel,Bos, Julia,Leverrier, Pauline,Espinosa, Leon,Szewczyk, Joanna,Vertommen, Didier,Iranzo, Olga,Collet, Jean-Fran?ois,Barras, Frédéric. "Repairing oxidized proteins in the bacterial envelope using respiratory chain electrons". . p. 409 - 412. Retrieved 2015.
• 3、 Mohrle,Hempel. "Determination of organic sulfides". . p. 903 - 913. Retrieved 1973.
• 4、 -. "Synthesis method of (2S)-2-(acetamino)-4-(methylsulfinyl)butyric acid". Paragraph 0019; 0020; 0021; 0022. . Retrieved 2019/01/08.