 | |
| Names | |
|---|---|
| IUPAC name (2S)-2-Amino-4-(S-methylsulfonimidoyl)butanoic acid | |
| Other names L-Methionine sulfoximine; MSO | |
| Identifiers | |
3D model (JSmol) | |
| 1725509 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.016.224 |
| EC Number |
|
| UNII | |
| |
| |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Methionine sulfoximine (MSO, also known asMetSox[1]) is an irreversibleglutamine synthetase inhibitor. It is thesulfoximine derivative ofmethionine withconvulsant effects.[2]
L-Methionine sulfoximine is composed of two differentdiastereomers, which areL-S-Methionine sulfoximine andL-R-Methionine sulfoximine. These affect thelongevity of themouse model forLou Gehrig's disease.[3] Overproduction ofglutamate results toexcitotoxicity, 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 isphosphorylated by glutamine synthetase. The resulting product acts as atransition state analog that is unable to diffuse from the active site, thereby inhibiting the enzyme.[5]
