Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:37:45 -0600 |
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Update Date | 2015-06-03 17:19:43 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | L-Methionine-(S)-S-oxide |
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Description | L-methionine-(s)-s-oxide is an oxidized form of methionine. Methionine is an amino acid susceptible to being oxidized to methionine sulfoxide (MetSO). The reduction of MetSO to methionine is catalyzed by methionine sulfoxide reductase (MSR), an enzyme present in almost all organisms. (PMID 20969952) Oxidation of methionine to methionine sulfoxide is a major oxidative stress product that reaches levels as high as 60% in cataract while being essentially absent from clear lenses. Methionine oxidation results in loss of protein function that can be reversed through the action of methionine sulfoxide reductase A (MsrA), which is implicated in oxidative stress protection and is an essential regulator of longevity in species ranging from Escherichia coli to mice. (PMID 15199188) |
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Structure | |
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Synonyms: | - 2-Amino-4-(methylsulfinyl)-Butanoate
- 2-Amino-4-(methylsulfinyl)-Butanoic acid
- 2-Amino-4-(methylsulfinyl)-Butyrate
- 2-Amino-4-(methylsulfinyl)-Butyric acid
- 2-Amino-4-(methylsulfinyl)butanoate
- 2-Amino-4-(methylsulfinyl)butanoic acid
- 2-Amino-4-(methylsulphinyl)-Butanoate
- 2-Amino-4-(methylsulphinyl)-Butanoic acid
- 2-Amino-4-(methylsulphinyl)-Butyrate
- 2-Amino-4-(methylsulphinyl)-Butyric acid
- 2-Amino-4-(methylsulphinyl)butanoate
- 2-Amino-4-(methylsulphinyl)butanoic acid
- DL-methionine sulfoxide
- DL-methionine sulphoxide
- L-Methionine (S)-S-oxide
- Methionine S-oxide
- Methionine sulfoxide
- Methionine sulphoxide
- Methionine, S-oxide
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Chemical Formula: | C5H11NO3S |
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Weight: | Average: 165.211 Monoisotopic: 165.045963913 |
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InChI Key: | QEFRNWWLZKMPFJ-KNODYTOMSA-N |
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InChI: | InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m1/s1 |
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CAS number: | 454-41-1 |
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IUPAC Name: | (2R)-2-amino-4-[(S)-methanesulfinyl]butanoic acid |
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Traditional IUPAC Name: | methionine sulfoxide |
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SMILES: | C[S@](=O)CC[C@@H](N)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | D-alpha-amino acids |
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Alternative Parents | |
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Substituents | - D-alpha-amino acid
- Thia fatty acid
- Fatty acid
- Fatty acyl
- Sulfoxide
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Sulfinyl compound
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Primary aliphatic amine
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Not Available |
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Charge: | 0 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | |
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References |
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References: | - Arias, D. G., Cabeza, M. S., Erben, E. D., Carranza, P. G., Lujan, H. D., Tellez Inon, M. T., Iglesias, A. A., Guerrero, S. A. (2011). "Functional characterization of methionine sulfoxide reductase A from Trypanosoma spp." Free Radic Biol Med 50:37-46. Pubmed: 20969952
- Kantorow, M., Hawse, J. R., Cowell, T. L., Benhamed, S., Pizarro, G. O., Reddy, V. N., Hejtmancik, J. F. (2004). "Methionine sulfoxide reductase A is important for lens cell viability and resistance to oxidative stress." Proc Natl Acad Sci U S A 101:9654-9659. Pubmed: 15199188
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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