CAS 15985-39-4|CAS 21752-31-8|L-METHIONINE SULFOXIMINE|L-methionine sulfoximine|L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine|(2S)-2-amino-4-[imino(methyl)oxo-$l^{6}-sulfanyl]butanoic acid|L-蛋氨...

General Information

Structure

Molecular Formula

C₅H₁₂N₂O₃S

Molecular Mass

180.22538

Exact Mass

180.05686325

Charge

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

Canonic Smiles

OC(=O)[C@H](CCS(=O)(=N)C)N

Isomeric Smiles

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

Calculated Properties

JChem

Acid pKa

1.8865596

H Acceptors

H Donor

LogD (pH = 5.5)

-4.447861

LogD (pH = 7.4)

-4.453787

Log P

-4.446533

Molar Refractivity

40.2168

Polarizability

16.919283

Polar Surface Area

104.24

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

L-METHIONINE SULFOXIMINEL-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximineL-蛋氨酸砜亚胺L-S-(3-氨基-3-羧丙基)-S-甲基砜亚胺L-Methionine sulfoximineL-S-[3-Amino-3-carboxypropyl]-S-methyl-[R,S]-sulfoximine(R)-L-S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine(2S,SR)-Methionine SulfoximineL-Methionine [R]-Sulfoximine[R-(R*,S*)]-2-Amino-4-(S-methylsulfonimidoyl)butanoic Acid(2S)-2-Amino-4-(S-methylsulfonimidoyl)butanoic AcidL-Methionine [R,S]-Sulfoximine

IUPAC Traditional name

L-methionine sulfoximine

IUPAC name

(2S)-2-amino-4-[imino(methyl)oxo-$l^{6}-sulfanyl]butanoic acid (2S)-2-amino-4-[imino(methyl)oxo-λ⁶-sulfanyl]butanoic acid

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

PubChem SID

Beilstein Number

MDL Number

Registration numbers

Properties

Physical Property

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02151619

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

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.

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

TRC

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

M260505

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity