(2S)-2-amino-4-[imino(methyl)oxo-λ6-sulfanyl]butanoic acid

• ChemBase ID: 103393
• Molecular Formular: C5H12N2O3S
• Molecular Mass: 180.22538
• Monoisotopic Mass: 180.05686325
• SMILES: CS(=N)(=O)CC[C@H](N)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CCS(=O)(=N)C)N
• InChI: InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1
• InChIKey: SXTAYKAGBXMACB-DPVSGNNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-[imino(methyl)oxo-λ^6-sulfanyl]butanoic acid; (2S)-2-amino-4-[imino(methyl)oxo-$l^{6}-sulfanyl]butanoic acid
• IUPAC Traditional name: L-methionine sulfoximine
• Synonyms: L-Methionine sulfoximine; L-S-[3-Amino-3-carboxypropyl]-S-methyl-[R,S]-sulfoximine; (2S)-2-Amino-4-(S-methylsulfonimidoyl)butanoic Acid; L-Methionine [R,S]-Sulfoximine; (R)-L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine; [R-(R*,S*)]-2-Amino-4-(S-methylsulfonimidoyl)butanoic Acid; (2S,SR)-Methionine Sulfoximine; L-Methionine [R]-Sulfoximine; L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine; L-METHIONINE SULFOXIMINE; L-S-(3-氨基-3-羧丙基)-S-甲基砜亚胺; L-蛋氨酸砜亚胺

Database IDs

• CAS Number: 15985-39-4; 21752-31-8
• MDL Number: MFCD00002621
• Beilstein Number: 6175446
• PubChem SID: 162091303; 24278555
• PubChem CID: 89034

CALCULATED PROPERTIES

• Acid pKa: 1.8865596
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.447861
• LogD (pH = 7.4): -4.453787
• Log P: -4.446533
• Molar Refractivity: 40.2168 cm^3
• Polarizability: 16.919283 Å^3
• Polar Surface Area: 104.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid; White Solid
• Melting Point: > 210°C; >210 °C (dec.)(lit.); >210°C (dec.); 233-236°C (dec.)
• Optical Rotation: [α]20/D +10.8 to +14.0°, c = 1 in H2O; [α]25/D +12.8°, c = 1 in H2O

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C; Refrigerator
• Storage Warning: Temperature Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-36; S:20-25-26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96% (rel., HPLC); 95-102% (w/w) (qNMR); 99%
• Grade: certified reference material; TraceCERT®
• Suitability: complies for H-NMR; complies for identity (HPLC)
• Impurities: ≤0.1% each single unknown impurity(rel.); ≤0.5% sulfated ash; ≤0.5% water (Karl Fischer); ≤1% methionine sulfone(rel.); ≤1% methionine sulfoxide(rel.); ≤10 mg/kg azide; ≤2% methionine(rel.); ≤20 ppm heavy metalls; ≤5000 ppm ethanol (GC-HS)
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality Level: GMP; PREMIUM
• Linear Formula: CH3S(O)(=NH)CH2CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02151619

Crystalline
Substrate for microbiological determination of L-methionine.
Inhibitor of glutamine transferase.

MP Biomedicals - 05225115

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M5379

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
As a potent inhibitor of glutamine sythetase activity, this reagent has widely been used as a selection agent for plasmid integration in Chinese hamster ovary (CHO) and other mammalian cell lines. The growing demand for high yield cell banks for production of recombinant proteins for therapeutics has resulted in two major systems for selection of stable and active clones, Methotrexate selection of dihydrofolate reductase (DHFR) overexpressing cells and MSX selection of glutamine synthetase overexpressing cells. Cells are grown in the absence of glutamine in the media and inhibition of the endogenous activity of glutamine synthease results in cell death for cells lacking overexpression. The MSX-glutamine synthase selection mechanism provides benefits over that of the Methotrexate-DHFR system in that it typically requires a single amplification step and results in significant reduction of time to produce high stability, highly amplified clones.
Biochem/physiol Actions
Methionine sulfoximine (MSX) increases ornithine decarboxylase activity, decreases the survival rate in a model of transient cerebral ischemia, and inhibits glutamine synthetase activity.

Sigma Aldrich - 91016

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M260500

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 by

Toronto Research Chemicals - M260505

The R-diastereoisomer of L-Methionine [R,S]-Sulfoximine (M260500).

REFERENCES

• Griffith, O.W., and Meister, A.: J. Biol. Chem. 254, 7558 (1979)
• Willard-Mack, C.L., et al: Neuroscience, 71, 2, 589 (1996)
• Wilson, J., et al.: J. Exp. Biol., 203, 2297 (2000)
• Ip, Y., et al.: J. Exp. Biol., 208, 1993 (2000)