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Names | |
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IUPAC name
(2S)-2-Amino-4-(S-methylsulfonimidoyl)butanoic acid | |
Other names
l-Methionine sulfoximine; MSO | |
Identifiers | |
3D model (JSmol) |
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1725509 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.016.224 ![]() |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C5H12N2O3S | |
Molar mass | 180.22 g·mol−1 |
Related compounds | |
Related compounds |
Buthionine sulfoximine Glufosinate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methionine sulfoximine (MSO, also known as MetSox[1]) is an irreversible glutamine synthetase inhibitor. It is the sulfoximine derivative of methionine with convulsant effects.[2]
Methionine sulfoximine is composed of two different diastereomers, which are L-S-Methionine sulfoximine and L-R-Methionine sulfoximine. These affect the longevity of the model mouse for Lou Gehrig's disease.[3] Overproduction of glutamate results to excitotoxicity, which kills the cell. Since methionine sulfoximine inhibits glutamate production in the brain, it prevents excitotoxicity. Thus, increasing the longevity of the mice.[4]
MSO is phosphorylated by glutamine synthetase. The resulting product acts as a transition state analog that is unable to diffuse from the active site, thereby inhibiting the enzyme.[5]
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GABA receptor antagonists |
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GABA synthesis inhibitors |
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Glycine receptor antagonists |
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Glutamate receptor agonists |
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Convulsant barbiturates |
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Other |
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