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Chemical Compound Review

S-methylmethionine     (3-amino-3-carboxy-propyl)- dimethyl-sulfanium

Synonyms: AG-K-71653, KST-1A5110, CTK0F5694, AR-1A3901, AC1L19A4, ...
 
 
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Disease relevance of S-methylmethionine

  • A model system was set up in E. coli which demonstrated that expression of the plant and, although to a much lesser degree, of the bacterial methyltransferase gene increases selenium tolerance and strongly reduces unspecific selenium incorporation into proteins, provided that S-methylmethionine is present in the medium [1].
 

High impact information on S-methylmethionine

 

Biological context of S-methylmethionine

  • Acid hydrolysis of dehulled soybean meal (SBM) and corn gluten meal (CGM) followed by chromatographic amino acid analysis (ninhydrin detection) revealed substantial quantities of S-methylmethionine (SMM) in both ingredients (1.65 g SMM/kg SBM; 0.5 g SMM/kg CGM) [7].
 

Anatomical context of S-methylmethionine

  • DMSP is known to be synthesized in the chloroplast from S-methylmethionine (SMM) imported from the cytosol, but the sizes of the chloroplastic and extrachloroplastic pools of these compounds are unknown [8].
  • The conversion rate from 14 C-cholesterol to its 7 alpha-hydroxylated metabolites was studied in the microsome system prepared from mice liver with the pretreatment of S-methylmethionine (MMSC) [9].
 

Associations of S-methylmethionine with other chemical compounds

 

Gene context of S-methylmethionine

References

  1. A family of S-methylmethionine-dependent thiol/selenol methyltransferases. Role in selenium tolerance and evolutionary relation. Neuhierl, B., Thanbichler, M., Lottspeich, F., Böck, A. J. Biol. Chem. (1999) [Pubmed]
  2. BRANCHED-CHAIN AMINOTRANSFERASE4 Is Part of the Chain Elongation Pathway in the Biosynthesis of Methionine-Derived Glucosinolates in Arabidopsis. Schuster, J., Knill, T., Reichelt, M., Gershenzon, J., Binder, S. Plant Cell (2006) [Pubmed]
  3. Transport of sulfonium compounds. Characterization of the s-adenosylmethionine and s-methylmethionine permeases from the yeast Saccharomyces cerevisiae. Rouillon, A., Surdin-Kerjan, Y., Thomas, D. J. Biol. Chem. (1999) [Pubmed]
  4. Purification and characterization of enzymes from Euglena gracilis that methylate methionine and arginine residues of cytochrome c. Farooqui, J.Z., Tuck, M., Paik, W.K. J. Biol. Chem. (1985) [Pubmed]
  5. Insertional inactivation of the methionine s-methyltransferase gene eliminates the s-methylmethionine cycle and increases the methylation ratio. Kocsis, M.G., Ranocha, P., Gage, D.A., Simon, E.S., Rhodes, D., Peel, G.J., Mellema, S., Saito, K., Awazuhara, M., Li, C., Meeley, R.B., Tarczynski, M.C., Wagner, C., Hanson, A.D. Plant Physiol. (2003) [Pubmed]
  6. Constitutive overexpression of cystathionine gamma-synthase in Arabidopsis leads to accumulation of soluble methionine and S-methylmethionine. Kim, J., Lee, M., Chalam, R., Martin, M.N., Leustek, T., Boerjan, W. Plant Physiol. (2002) [Pubmed]
  7. Dietary S-methylmethionine, a component of foods, has choline-sparing activity in chickens. Augspurger, N.R., Scherer, C.S., Garrow, T.A., Baker, D.H. J. Nutr. (2005) [Pubmed]
  8. Salinity promotes accumulation of 3-dimethylsulfoniopropionate and its precursor S-methylmethionine in chloroplasts. Trossat, C., Rathinasabapathi, B., Weretilnyk, E.A., Shen, T.L., Huang, Z.H., Gage, D.A., Hanson, A.D. Plant Physiol. (1998) [Pubmed]
  9. A possible activation of cholesterol 7-hydroxylation by S-methylmethionine (vitamin U). Matsuo, T., Seri, K., Kato, T. Arzneimittel-Forschung. (1980) [Pubmed]
  10. The S-methylmethionine cycle in angiosperms: ubiquity, antiquity and activity. Ranocha, P., McNeil, S.D., Ziemak, M.J., Li, C., Tarczynski, M.C., Hanson, A.D. Plant J. (2001) [Pubmed]
  11. S-methylmethionine metabolism in Escherichia coli. Thanbichler, M., Neuhierl, B., Böck, A. J. Bacteriol. (1999) [Pubmed]
  12. Effects of S-methylmethionine (vitamin U) on experimental nephrotic hyperlipidemia. Seri, K., Amemiya, K., Sugimoto, H., Kato, T. Arzneimittel-Forschung. (1979) [Pubmed]
  13. Mechanisms to account for maintenance of the soluble methionine pool in transgenic Arabidopsis plants expressing antisense cystathionine gamma-synthase cDNA. Gakière, B., Ravanel, S., Droux, M., Douce, R., Job, D. C. R. Acad. Sci. III, Sci. Vie (2000) [Pubmed]
  14. Evidence implicating dimethylsulfoniopropionaldehyde as an intermediate in dimethylsulfoniopropionate biosynthesis. James, F., Paquet, L., Sparace, S.A., Gage, D.A., Hanson, A.D. Plant Physiol. (1995) [Pubmed]
 
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