Methionine sulfoximine

Methionine sulfoximine
Names
IUPAC name
2-Amino-4-(S-methylsulfonimidoyl)butanoic acid
Other names
MSO
Identifiers
3D model (JSmol)
1725509
ChEBI
ChemSpider
EC Number 217-845-8
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).
Infobox references

Methionine sulfoximine (MSO) is an irreversible glutamine synthetase inhibitor. It's the sulfoximine derivative of methionine with convulsant effects.[1]

Mechanism of action

Phosphorylation of MSO by glutamine synthetase.

MSO is phosphorylated by glutamine synthetase. The resulting product acts as a transition state analog that irreversibly binds to the glutamine synthetase, thereby inhibiting the enzyme.[2]




See also

References

  1. ↑ Rowe, WB; Meister, A (June 1970). "Identification of L-methionine-S-sulfoximine as the convulsant isomer of methionine sulfoximine". Proceedings of the National Academy of Sciences of the United States of America. 66 (2): 500–6. PMC 283073. PMID 4393740.
  2. ↑ Krajewski, W. W.; Jones, T. A.; Mowbray, S. L. (18 July 2005). "Structure of Mycobacterium tuberculosis glutamine synthetase in complex with a transition-state mimic provides functional insights". Proceedings of the National Academy of Sciences. 102 (30): 10499–10504. doi:10.1073/pnas.0502248102. PMC 1180770. PMID 16027359.
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