| 词条 | S-Methylmethionine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 434499762 | Name =S-Methylmethionine | Reference = [1] | ImageFile = Methylmethionine.png | ImageSize = | IUPACName = (3-Amino-3-carboxy-propyl)-dimethyl-sulfonium | OtherNames = S-Methyl-L-methionine Vitamin U |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 4727-40-6 | PubChem = 145692 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 128519 | InChI = 1/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1/t5-/m0/s1 | InChIKey = YDBYJHTYSHBBAU-YJIVXYNWBY | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1/t5-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = YDBYJHTYSHBBAU-YFKPBYRVSA-O | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 17728 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C03172 | SMILES = C[S+](C)CC[C@@H](C(=O)O)N }} |Section2={{Chembox Properties | Formula = C6H14NO2S+ | MolarMass = 164.243 g/mol | Appearance = | Density = | MeltingPtC = 139 | MeltingPt_ref = [1] (bromide salt, decomposes) {{convert|134|C|F}}[1] (chloride salt, decomposes) | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | LD50 = 2760 mg/kg (iv, mice, chloride salt)[1] }} }}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. Biosynthesis and biochemical functionS-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.[5] S-Methylmethionine is claimed to have protective effects in the gastrointestinal mucosa and in the liver.[6]Beer flavor precursor in barley maltS-Methylmethionine is found in barley and is further created during the malting process. SMM can be subsequently converted to DMS during the malt kilning process. Lightly kilned malts such as pilsner or lager malts retain much of their SMM content while higher kilned malt such as pale ale malt has substantially more of the SMM converted to DMS in the malt. Darker kilned malts such as Munich malt have virtually no SMM content since most has been converted to DMS. Other crystal malts and roasted malts have no SMM content and often no DMS content since the kilning also drives that compound out of the malt. [7][8]References1. ^1 2 3 Merck Index, 12th ed., 10165 {{ISBN|0-911910-12-3}} 2. ^1 2 {{cite journal | doi = 10.1105/tpc.11.8.1485 | title = S-methylmethionine plays a major role in phloem sulfur transport and is synthesized by a novel type of methyltransferase | year = 1999 | author = Bourgis F | journal = The Plant Cell Online | volume = 11 | issue = 8 | pages = 1485–1498 | pmc = 144290 }} 3. ^{{cite web|author=National Center for Biomedical Ontology |title=Methylmethionine Sulfonium Chloride|url=http://bioportal.bioontology.org/ontologies/46317/?p=terms&conceptid=Methylmethionine_Sulfonium_Chloride}} 4. ^{{cite journal | author = Cheney G| title = Anti-peptic ulcer dietary factor (vitamin "U") in the treatment of peptic ulcer | journal = J Am Diet Assoc |volume = 26 | issue = 9 | pages = 668–72 |date=September 1950 | pmid = 15436263 | doi = | url = }} 5. ^{{cite journal | doi = 10.1104/pp.120.4.945 | title = Betaines and related osmoprotectants. Targets for metabolic engineering of stress resistance | year = 1999 | author = McNeil SD | journal = Plant Physiology | volume = 120 | issue = 4 | pages = 945–949| pmc = 1539222 }} 6. ^{{cite journal |vauthors=Patel AD, Prajapati NK | year = 2012 | title = Review on Biochemical Importance of Vitamin-U | journal = Journal of Chemical and Pharmaceutical Research | volume = 4 | issue = 1 | pages = 209–215 | url = http://jocpr.com/vol4-iss1-2012/JCPR-2012-4-1-209-215.pdf }} 7. ^Pitz, W. Factors affecting S-Methylmethione levels in malt, Journal of American Society of Brewing Chemists, 1987. 8. ^{{cite book | title=Brewing | publisher=Royal Society of Chemistry | year = 1999 | author = Hornsey IS | isbn = 9780854045686 | page=47}} External links
4 : Amino acids|Sulfur amino acids|Sulfur ions|Methylation |
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