L-METHIONINE SULFOXIMINE

L-METHIONINE SULFOXIMINE Basic information
Product Name:L-METHIONINE SULFOXIMINE
Synonyms:2-AMINO-4-(S-METHYLSULFONIMIDOSYL)BUTANOIC ACID;L-S-[3-AMINO-3-CARBOXYPROPYL]-S-METHYLSULFOXIMINE;L-METHIONINE SULFOXIMINE;L-METHIONINE-DL-SULFOXIMINE;L-Methionine [R,S]-Sulfoximine;L-S-[3-Amino-3-carboxypropyl]-S-methyl-[R,S]-sulfoximine;(2S)-2-Amino-4-(S-methylsulfonimidosyl)butanoic acid;L-Methionine sulfoximine, 98+%
CAS:15985-39-4
MF:C5H12N2O3S
MW:180.23
EINECS:629-483-1
Product Categories:Sulfur & Selenium Compounds;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives
Mol File:15985-39-4.mol
L-METHIONINE SULFOXIMINE Structure
L-METHIONINE SULFOXIMINE Chemical Properties
Melting point >210 °C (dec.)(lit.)
Boiling point 352.2±52.0 °C(Predicted)
density 1.215 (estimate)
refractive index 1.6430 (estimate)
storage temp. 20-25°C
solubility Aqueous Base (Slightly), Formic Acid (Slightly), Water (Sparingly, Sonicated)
form Crystalline Powder
color White or almost white
optical activity[α]20/D +10.8 to +14.0°, c = 1 in H2O
BRN 6175446
Stability:Temperature Sensitive
CAS DataBase Reference15985-39-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
HazardClass IRRITANT
HS Code 29309090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
L-METHIONINE SULFOXIMINE Usage And Synthesis
Chemical PropertiesWhite Crystalline Powder
UsesMethionine 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
Usesglutamine synthetase inhibitor, ornithine decarboxylase enhancer, convulsant
UsesL-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity.
DefinitionChEBI: L-methionine sulfoximine is a methionine sulfoximine in which the amino group has S-stereochemistry. It has a role as a geroprotector and an EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor. It is a methionine sulfoximine, a L-methionine derivative and a non-proteinogenic L-alpha-amino acid. It is a tautomer of a L-methionine sulfoximine zwitterion.
Biochem/physiol ActionsAs a potent inhibitor of glutamine synthetase activity (GS), 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 synthetase results in cell death for cells lacking overexpression. The MSX-glutamine synthetase 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. L-Methionine sulfoximine (MSX) enhances NH3 production in seedling leaves wheat, barley, corn and sorghum plants by inhibiting GS activity. MSX increases ornithine decarboxylase activity and decreases the survival rate in a model of transient cerebral ischemia.
L-METHIONINE SULFOXIMINE Preparation Products And Raw materials
Homocysteine DL-METHIONINOL DL-Homocysteine DL-METHIONINE SULFOXIDE DL-METHIONINE SULFOXIMINE Butanethiol 4-MERCAPTOBUTYRIC ACID FMOC-L-BUTHIONINESULFOXIMINE DL-Methionine 4-MERCAPTO-1-BUTANOL 1-Propanethiol 4-(METHYLTHIO)BUTANOL L-METHIONINE SULFOXIMINE Methanol Dimethyl sulfoxide L-Methioninol Methylthioethane L-Methionine

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