Methionine sulfoximine

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l-Methionine sulfoximine
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 Edit this at Wikidata
EC Number
  • 217-845-8
UNII
  • 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
    Key: SXTAYKAGBXMACB-DPVSGNNYSA-N
  • CS(=N)(=O)CC[C@@H](C(=O)O)N
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).

Methionine sulfoximine (MSO, also known as MetSox

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]

Mechanism of action

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]

Phosphorylation of MSO by glutamine synthetase

References

  1. PMID 21875360
    .
  2. PMID 4393740
    .
  3. S2CID 45664203
    .
  4. PMID 23217569
    .
  5. PMID 16027359
    .
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