Methionine sulfone

Methionine sulfone
Names
	IUPAC name S,S-dioxo-L-methionine
Identifiers
CAS Number	±: 820-10-0 racemic; L: 7314-32-1 L enantiomer; D: 41486-92-4 D;
3D model (JSmol)	±: Interactive image;
ChEBI	L: CHEBI:21363;
ChEMBL	L: ChEMBL442720;
ChemSpider	L: 392966;
DrugBank	L: DB03790;
ECHA InfoCard	100.027.976
EC Number	L: 230-774-7;
PubChem CID	L: 445282;
UNII	L: V3Z9QH81BX;
CompTox Dashboard (EPA)	±: DTXSID301350027 ;
	InChI InChI=1S/C5H11NO4S/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 Key: UCUNFLYVYCGDHP-BYPYZUCNSA-N; L: InChI=1S/C5H11NO4S/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 Key: UCUNFLYVYCGDHP-BYPYZUCNSA-N;
	SMILES ±: CS(=O)(=O)CC[C@@H](C(=O)O)N;
Properties
Chemical formula	C5H11NO4S
Molar mass	181.21 g·mol−1
Appearance	white solid
Melting point	250–251 °C (482–484 °F; 523–524 K) single enantiomer
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methionine sulfone is the organic compound with the formula CH₃SO₂CH₂CH₂CH(NH₂)CO₂H. Although it is an amino acid that occurs naturally, it is formed post-translationally, arising by the double oxidation of methionine via the intermediate methionine sulfoxide.^[1]^[2] The methionine sulfone residue is found in the enzyme catalase of the bacterium Proteus mirabilis.^[3]

References

^ Bin, P; Huang, R; Zhou, X (2017). "Oxidation Resistance of the Sulfur Amino Acids: Methionine and Cysteine". BioMed Research International. 2017 9584932. doi:10.1155/2017/9584932. PMC 5763110. PMID 29445748.
^ Lee BC, Dikiy A, Kim HY, Gladyshev VN (2009). "Functions and evolution of selenoprotein methionine sulfoxide reductases". Biochimica et Biophysica Acta (BBA) - General Subjects. 1790 (11): 1471–1477. doi:10.1016/j.bbagen.2009.04.014. PMC 3062201. PMID 19406207.
^ Buzy, Armelle; Bracchi, Valérie; Sterjiades, Raja; Chroboczek, Jadwiga; Thibault, Pierre; Gagnon, Jean; Jouve, Hélène Marie; Hudry-Clergeon, Gilbert (1995). "Complete Amino Acid Sequence of Proteus mirabilis PR Catalase. Occurrence of a Methionine sulfone in the Close Proximity of the Active Site". Journal of Protein Chemistry. 14 (2): 59–72. doi:10.1007/bf01888363. PMID 7786407.