Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Methionine sulfoxide is the organic compound with the formula CH3S(O)CH2CH2CH(NH2)CO2H. It is an amino acid that occurs naturally although it is formed post-translationally.
Oxidation of the sulfur of methionine results in methionine sulfoxide or methionine sulfone. The sulfur-containing amino acids methionine and cysteine are more easily oxidized than the other amino acids.[1][2] Unlike oxidation of other amino acids, the oxidation of methionine can be reversed by enzymatic action, specifically by enzymes in the methionine sulfoxide reductase family of enzymes. The three known methionine sulfoxide reductases are MsrA, MsrB, and fRmsr.[2] Oxidation of methionine results in a mixture of the two diastereomers methionine-S-sulfoxide and methionine-R-sulfoxide, which are reduced by MsrA and MsrB, respectively.[3] MsrA can reduce both free and protein-based methionine-S-sulfoxide, whereas MsrB is specific for protein-based methionine-R-sulfoxide. fRmsr, however, catalyzes the reduction of free methionine-R-sulfoxide.[2] Thioredoxin serves to recycle by reduction some of the methionine sulfoxide reductase family of enzymes, whereas others can be reduced by metallothionein.[4]
^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.
^ abcLee 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.
^Kim HY, Gladyshev VN (2004). "Methionine sulfoxide reduction in mammals: characterization of methionine-R-sulfoxide reductases". Molecular Biology of the Cell. 15 (3): 1055–1064. doi:10.1091/mbc.E03-08-0629. PMC 363075. PMID 14699060.
^Sagher D, Brunell D, Hejtmancik JF, Kantorow M, Brot N, Weissbach H (2006). "Thionein can serve as a reducing agent for the methionine sulfoxide reductases". Proceedings of the National Academy of Sciences of the United States of America. 103 (23): 8656–8661. Bibcode:2006PNAS..103.8656S. doi:10.1073/pnas.0602826103. PMC 1592241. PMID 16735467.
and 20 Related for: Methionine sulfoxide information
Oxidation of the sulfur of methionine results in methioninesulfoxide or methionine sulfone. The sulfur-containing amino acids methionine and cysteine are more...
Methioninesulfoxide reductase may refer to: Methionine-S-oxide reductase L-methionine (S)-S-oxide reductase This set index page lists enzyme articles...
Peptide methioninesulfoxide reductase may refer to: Protein-methionine-S-oxide reductase Peptide-methionine (S)-S-oxide reductase This set index page...
Another commercially important sulfoxides include armodafinil. Methioninesulfoxide forms from the amino acid methionine and its accumulation is associated...
exceptions where methionine may act as a redox sensor (e.g.,methioninesulfoxide), methionine residues do not have a catalytic role. This is in contrast...
Methionine-R-sulfoxide reductase B1 is an enzyme that in humans is encoded by the SEPX1 gene. This gene encodes a selenoprotein, which contains a selenocysteine...
Acetylmethionine sulfoxide reductase may refer to: Methionine-S-oxide reductase L-methionine (S)-S-oxide reductase This set index page lists enzyme articles...
Methionine-R-sulfoxide reductase B2, mitochondrial is an enzyme that in humans is encoded by the MSRB2 gene. The MRSB2 enzyme catalyzes the reduction of...
Gladyshev VN (2009). "Functions and evolution of selenoprotein methioninesulfoxide reductases". Biochimica et Biophysica Acta (BBA) - General Subjects...
antioxidant defense by reducing dehydroascorbate, peroxiredoxins, and methioninesulfoxide reductase. Beside their function in antioxidant defense, bacterial...
because it dissolves most proteins. Also, the oxidation of methionine to methioninesulfoxide, which is inert to BrCN attack, occurs more readily in HCl...
substrates, besides having chaperone activity Oxidation of surface exposed methionine residues surrounding the entrance to the active site could function as...
compounds—sulfur is vital for life. Of the 20 common amino acids, two (cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa...
dehydrogenases, glycine reductases, selenophosphate synthetase 2, methionine-R-sulfoxide reductase B1 (SEPX1), and some hydrogenases). It occurs in all three...
DMS is also produced naturally by bacterial transformation of dimethyl sulfoxide (DMSO) waste that is disposed of into sewers, where it can cause environmental...
cycle. Sulfoxides and sulfones are thioethers with one and two oxygen atoms attached to the sulfur atom, respectively. The simplest sulfoxide, dimethyl...
cycle. Sulfoxides and sulfones are thioethers with one and two oxygen atoms attached to the sulfur atom, respectively. The simplest sulfoxide, dimethyl...
"The sRNA RyhB regulates the synthesis of the Escherichia coli methioninesulfoxide reductase MsrB but not MsrA". PLOS ONE. 8 (5): e63647. Bibcode:2013PLoSO...
iodide: S(CH3)2 + CH3I → [S(CH3)3]+I− Sulfides also oxidize easily to sulfoxides (R−S(=O)−R), which can themselves be further oxidized to sulfones (R−S(=O)2−R)...
Global Information
