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
ECHA InfoCard 100.013.365 Edit this at Wikidata
EC Number
  • L-enantiomer: 214-701-6
KEGG
UNII
  • InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
    Key: IDIDJDIHTAOVLG-VKHMYHEASA-N
  • L-enantiomer: CSC[C@@H](C(=O)O)N
Properties
C4H9NO2S
Molar mass 135.18 g·mol−1
Appearance white solid
Melting point 248 °C (478 °F; 521 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Biosynthesis

The amino acid 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.[2][3]

Beyond its biological context, it has been examined as a chelating agent.[4]

References

  1. ^ Maw, George A. (1982). "Biochemistry of S-Methyl-L-Cysteine and its Principal Derivatives". Sulfur Reports. 2: 1–26. doi:10.1080/01961778208082422.
  2. ^ 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.
  3. ^ 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. PMC 6036201. PMID 29743234.
  4. ^ 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.
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