Merck
All Photos(5)

M5379

Sigma-Aldrich

L-Methionine sulfoximine

Synonym(s):
L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine
Linear Formula:
CH3S(O)(=NH)CH2CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
180.23
Beilstein:
6175446
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

mp

>210 °C (dec.) (lit.)

SMILES string

CS(=N)(=O)CC[C@H](N)C(O)=O

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

InChI key

SXTAYKAGBXMACB-DPVSGNNYSA-N

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Application

L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity.[1][2]

Packaging

250, 500 mg in poly bottle
1, 5 g in poly bottle

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.[3] MSX increases ornithine decarboxylase activity and decreases the survival rate in a model of transient cerebral ischemia.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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