Chemistry:S-Methylcysteine
| |
| Names | |
|---|---|
| IUPAC name
S-Methyl-L-cysteine
| |
| Systematic IUPAC name
2-amino-3-(methylthio)propanoic acid | |
| Other names
3-methylthioalanine
| |
| Identifiers | |
| |
3D model (JSmol)
|
|
| ChEBI |
|
| ChEMBL |
|
| ChemSpider |
|
| DrugBank |
|
| EC Number |
|
| KEGG |
|
PubChem CID
|
|
| UNII |
|
| |
| |
| Properties | |
| C4H9NO2S | |
| Molar mass | 135.18 g·mol−1 |
| Appearance | white solid |
| Melting point | 248 °C (478 °F; 521 K) |
| Hazards | |
| GHS pictograms | 
|
| GHS Signal word | Warning |
| H302, H315, H319, H335 | |
| P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
S-Methylcysteine is the amino acid with the nominal formula CH3SCH2CH(NH2)CO2H. It is the S-methylated derivative of cysteine. This amino acid occurs widely in plants, including many edible vegetables.[1]
Natural occurrence
S-Methylcysteine is not genetically coded, but it arises by post-translational methylation of cysteine. One pathway involves methyl transfer from alkylated DNA by zinc-cysteinate-containing repair enzymes such as methylated-DNA-protein-cysteine methyltransferase.[2][3]
S-Methylcysteine sulfoxide is an oxidized derivative of S-methylcysteine that is found in onions.[4]
MetaCyc contains a list of biochemical reactions producing and consuming this substance.[5]
Other chemical properties
Beyond its biological context, S-methylcysteine has been examined as a chelating agent.[6]
References
- ↑ Maw, George A. (1982). "Biochemistry of S-Methyl-L-Cysteine and its Principal Derivatives". Sulfur Reports 2: 1–26. doi:10.1080/01961778208082422.
- ↑ Sors, Thomas G.; Ellis, Danielle R.; Na, Gun Nam; Lahner, Brett; Lee, Sangman; Leustek, Thomas; Pickering, Ingrid J.; Salt, David E. (2005). "Analysis of Sulfur and Selenium Assimilation in Astragalus plants with Varying Capacities to Accumulate Selenium". The Plant Journal 42 (6): 785–797. doi:10.1111/j.1365-313X.2005.02413.x. PMID 15941393.
- ↑ Clarke, Steven G. (2018). "The ribosome: A Hot Spot for the Identification of New Types of Protein Methyltransferases". Journal of Biological Chemistry 293 (27): 10438–10446. doi:10.1074/jbc.AW118.003235. PMID 29743234.
- ↑ Bernaert, N.; Goetghebeur, L.; De Clercq, H.; De Loose, M.; Daeseleire, E.; Van Pamel, E.; Van Bockstaele, E.; Van Droogenbroeck, B. (2012). "Influence of Cultivar and Harvest Time on the Amounts of Isoalliin and Methiin in Leek (Allium ampeloprasum var. porrum).". Journal of Agricultural and Food Chemistry 60 (44): 10910–10919. doi:10.1021/jf302132a. PMID 23020262. Bibcode: 2012JAFC...6010910B.
- ↑ "S-methyl-L-cysteine". https://biocyc.org/compound?orgid=META&id=S-METHYL-L-CYSTEINE#RXNS.
- ↑ He, Haiyang; Lipowska, Malgorzata; Xu, Xiaolong; Taylor, Andrew T.; Carlone, Maria; Marzilli, Luigi G. (2005). "Re(CO)3 Complexes Synthesized via an Improved Preparation of Aqueousfac-[Re(CO)3(H2O)3]+as an Aid in Assessing 99m Tc Imaging Agents. Structural Characterization and Solution Behavior of Complexes with Thioether-Bearing Amino Acids as Tridentate Ligands". Inorganic Chemistry 44 (15): 5437–5446. doi:10.1021/ic0501869. PMID 16022542.
 |  |
