Methionine sulfoximine

Methionine sulfoximine
Names
	IUPAC name 2-Amino-4-(S-methylsulfonimidoyl)butanoic acid
	Other names MSO
Identifiers
CAS Number	1982-67-8;
3D model (JSmol)	Interactive image;
Beilstein Reference	1725509
ChEBI	CHEBI:47833;
ChemSpider	15302;
ECHA InfoCard	100.016.224
EC Number	217-845-8;
PubChem CID	16118;
CompTox Dashboard (EPA)	DTXSID201031266 ;
	InChI InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9) Key: SXTAYKAGBXMACB-UHFFFAOYSA-N;
	SMILES CS(=N)(=O)CCC(C(=O)O)N;
Properties
Chemical formula	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

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]

References

^ 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.
^ 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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[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.

[1]

[2]

v t e Convulsants
GABA receptor antagonists	Bicuculline Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Chlorophenylsilatrane Cicutoxin Cloflubicyne Coriamyrtin Dihydropicrotoxinin DMCM EBOB Endosulfan FG-7142 Fipronil Flurothyl Gabazine Oenanthotoxin Pentylenetetrazol Phenylsilatrane Picrotoxin p-CN-TBOB p-NCS-TBOB RDX TBOB Tetramethylenedisulfotetramine Thujone Trimethylolpropane phosphite Tutin
GABA synthesis inhibitors	3-Mercaptopropionic acid 4-Deoxypyridoxine Allylglycine Crimidine Decaborane Ginkgotoxin Isoniazid Pentaborane Thiocarbohydrazide Toxopyrimidine
Glycine receptor antagonists	Coriamyrtin Dendrobine Picrotoxin Strychnine Tutin
Glutamate receptor agonists	AMPA Domoic acid Kainic acid NMDA Quisqualic acid Tetrazolylglycine
Convulsant barbiturates	CHEB DMBB McN-481
Other	2,2,3,3-Tetrafluoropropyl trifluoromethyl ether Bromocamphor Camphor FAZ-4 Fluoroethyl fluoroacetate MC-2973 Methionine sulfoximine Methyl fluoroacetate Nitrocyclohexane Thebaine

Mechanism of action

See also

References