S-Methylmethionine

S-Methylmethionine[1]
Names
IUPAC name
(3-Amino-3-carboxy-propyl)-dimethyl-sulfonium
Other names
S-Methyl-L-methionine
Vitamin U
Identifiers
4727-40-6 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17728 N
ChemSpider 128519 N
KEGG C03172 N
PubChem 145692
Properties
C6H14NO2S+
Molar mass 164.243 g/mol
Melting point 139 °C (282 °F; 412 K)[1] (bromide salt, decomposes)
134 °C (273 °F)[1] (chloride salt, decomposes)
Hazards
Lethal dose or concentration (LD, LC):
2760 mg/kg (iv, mice, chloride salt)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

S-Methylmethionine (SMM) is a derivative of methionine with the chemical formula (CH3)2S+CH2CH2CH(NH3+)CO2−. This cation is an intermediate in many biosynthetic pathways owing to the sulfonium functional group. The natural derivative S-methylmethionine is biosynthesized from L-methionine which is first converted to S-adenosylmethionine. The subsequent conversion, involving replacement of the adenosyl group by a methyl group is catalyzed by the enzyme methionine S-methyltransferase. S-methylmethionine is particularly abundant in plants, being more abundant than methionine.[2]

S-Methylmethionine is sometimes referred to as vitamin U,[3] but it is not considered a true vitamin. The term was coined in 1950 by Garnett Cheney for uncharacterized anti-ulcerogenic[4] factors in raw cabbage juice that may help speed healing of peptic ulcers.

S-Methylmethionine is claimed to have protective effects in the gastrointestinal mucosa and in the liver.[5]

Biosynthesis and biochemical function

S-Methylmethionine arises via the methylation of methionine by S-adenosyl methionine (SAM). The coproduct is S-adenosyl homocysteine.[2]

The biological roles of S-methylmethionine are not well understood. Speculated roles include methionine storage, use as a methyl donor, regulation of SAM.[2] A few plants use S-methylmethionine as a precursor to the osmolyte dimethylsulfoniopropionate (DMSP). Intermediates include dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.[6]

Beer flavor precursor in barley malt

S-Methylmethionine is found in barley and during the malting process, particularly the curing stage in kilning, heat causes it to break down to form dimethyl sulfide (DMS).[7]

References

  1. 1 2 3 4 Merck Index, 12th ed., 10165 ISBN 0-911910-12-3
  2. 1 2 3 Bourgis F (1999). "S-methylmethionine plays a major role in phloem sulfur transport and is synthesized by a novel type of methyltransferase". The Plant Cell Online. 11 (8): 1485–1498. doi:10.1105/tpc.11.8.1485.
  3. ↑ National Center for Biomedical Ontology. "Methylmethionine Sulfonium Chloride".
  4. ↑ Cheney G (September 1950). "Anti-peptic ulcer dietary factor (vitamin "U") in the treatment of peptic ulcer". J Am Diet Assoc. 26 (9): 668–72. PMID 15436263.
  5. ↑ Patel AD, Prajapati NK (2012). "Review on Biochemical Importance of Vitamin-U" (PDF). Journal of Chemical and Pharmaceutical Research. 4 (1): 209–215.
  6. ↑ McNeil SD (1999). "Betaines and related osmoprotectants. Targets for metabolic engineering of stress resistance". Plant Physiology. 120 (4): 945–949. doi:10.1104/pp.120.4.945.
  7. ↑ Hornsey IS (1999). Brewing. Royal Society of Chemistry. p. 47. ISBN 9780854045686.
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