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 Reference

15985-39-4(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

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

L-METHIONINE SULFOXIMINE Usage And Synthesis

Chemical Properties

White Crystalline Powder

Uses

glutamine synthetase inhibitor, ornithine decarboxylase enhancer, convulsant

Uses

L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity.

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

Definition

ChEBI: 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 Actions

As 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(15985-39-4)Related Product Information

• Methanol
• Dimethyl sulfoxide
• 4-(METHYLTHIO)BUTANOL
• DL-METHIONINE SULFOXIDE
• L-Methioninol
• L-Methionine
• DL-Homocysteine
• 3-aminopropanethiol
• 3-(METHYLTHIO)PROPYLAMINE
• Ammonium sulfide
• N-BUTYL METHYL SULFIDE
• L-BUTHIONINE-(S,R)-SULFOXIMINE
• METHYL PROPYL SULFIDE
• Butanethiol
• DL-Methionine
• 4-MERCAPTO-1-BUTANOL
• 1-Propanethiol
• L-METHIONINE SULFOXIMINE