Chemistry:Methionine sulfone

From HandWiki
Methionine sulfone
Names
IUPAC name
S,S-dioxo-L-methionine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • L: 230-774-7
UNII
Properties
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 CH
3
SO
2
CH
2
CH
2
CH(NH
2
)CO
2
H
. 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

  1. Bin, P; Huang, R; Zhou, X (2017). "Oxidation Resistance of the Sulfur Amino Acids: Methionine and Cysteine.". BioMed Research International 2017. doi:10.1155/2017/9584932. PMID 29445748. 
  2. "Functions and evolution of selenoprotein methionine sulfoxide reductases". Biochimica et Biophysica Acta (BBA) - General Subjects 1790 (11): 1471–1477. 2009. doi:10.1016/j.bbagen.2009.04.014. PMID 19406207. 
  3. 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.