Methionine sulfoximine zwitterion

Base Information

• Chemical Name: Methionine sulfoximine zwitterion
• CAS No.: 15985-39-4
• Molecular Formula: C5H12N2O3S
• Molecular Weight: 180.228
• Hs Code.: 29309090
• Mol file: 15985-39-4.mol

Synonyms:L-methionine-D,L-sulphoximine;methionine sulfoximine zwitterion;CHEBI:87826;L-methionine sulfoximine zwitterion;(2S)-2-azaniumyl-4-(S-methanesulfonimidoyl)butanoate

Chemical Property of Methionine sulfoximine zwitterion

Chemical Property:

• Appearance/Colour: White Crystalline Powder
• Melting Point: >210oC (dec.)(lit.)
• Refractive Index: 1.6430 (estimate)
• Boiling Point: 352.2 °C at 760 mmHg
• Flash Point: 166.8 °C
• PSA: 112.62000
• Density: 1.46 g/cm³
• LogP: 1.13070
• Storage Temp.: 0-6°C
• Solubility.: Aqueous Base (Slightly), Formic Acid (Slightly), Water (Sparingly, Sonicated)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 180.05686342
• Heavy Atom Count: 11
• Complexity: 239

Purity/Quality:

99%, ^*data from raw suppliers

L-Methionine [R,S]-Sulfoximine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=N)(=O)CCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: CS(=N)(=O)CC[C@@H](C(=O)[O-])[NH3+]
• Uses: Methionine sulfoximine inhibits both glutamine synthetase and g-glutamylcysteine synthetase. Working concentrations for inhibition of g-glutamylcysteine synthetase are 0.2-2.0 mM (52% inhibition occured at 100 mM). Methionine sulfoximine is also a toxic glutamine synthetase inhibitor, ornithine decarboxylase enhancer, convulsant L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity.

Technology Process of Methionine sulfoximine zwitterion

There total 7 articles about Methionine sulfoximine zwitterion 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: 66.0%

tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-[N-(tert-butoxycarbonyl)-S-methylsulfonimidoyl]-butanoate → L-methionine sulfoximine (15985-39-4)

Guidance literature:

With hydrogenchloride; water; at 80 ℃; for 3h;

DOI:10.1021/acs.joc.5b00844

Reference yield:

C13H14N2O5S (87141-35-3,87141-36-4) → L-methionine-R-sulfoximine (1982-67-8,15985-39-4,21056-59-7,21752-31-8,21752-32-9,121249-45-4,121249-46-5)

Guidance literature:

Multi-step reaction with 2 steps

1: (CH₃CO)2O / 6 h / Ambient temperature; Alternatively DCC, 3 hr, 0 deg C; 9 hr, room temp., pH 3 may also be used.

2: hydrolysis and deblocking

With acetic anhydride;

DOI:10.1016/S0040-4039(00)81684-6

Reference yield:

L-methionine-S,R-sulfoximine (21056-59-7) → L-methionine-R-sulfoximine (1982-67-8,15985-39-4,21056-59-7,21752-31-8,21752-32-9,121249-45-4,121249-46-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.5 hr, 0 deg C; 15 hr, room temp.

2: (CH₃CO)2O / 6 h / Ambient temperature; Alternatively DCC, 3 hr, 0 deg C; 9 hr, room temp., pH 3 may also be used.

3: hydrolysis and deblocking

With acetic anhydride;

DOI:10.1016/S0040-4039(00)81684-6

upstream raw materials:

2-((1R,4R)-1-Methyl-1,3-dioxo-3,4,5,6-tetrahydro-1λ⁶-[1,2]thiazin-4-yl)-isoindole-1,3-dione

C₁₃H₁₄N₂O₅S

L-methionine-S,R-sulfoximine

2-((1S,4R)-1-Methyl-1,3-dioxo-3,4,5,6-tetrahydro-1λ⁶-[1,2]thiazin-4-yl)-isoindole-1,3-dione

Downstream raw materials:

2(S)-methionine S(R)-sulfoximine

2(S)-methionine S(S)-sulfoximine

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