塩化メチルメチオニンスルホニウムクロライド、メチルメチオニンスルホニウムクロリド

関: methylmethionine

WordNet

any compound containing a chlorine atom
any salt of hydrochloric acid (containing the chloride ion)

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塩化物

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/08 21:05:42」(JST)

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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

^ ^a ^b ^c ^d Merck Index, 12th ed., 10165 ISBN 0-911910-12-3
^ ^a ^b ^c 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.
^ National Center for Biomedical Ontology. "Methylmethionine Sulfonium Chloride".
^ 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.
^ Patel AD, Prajapati NK (2012). "Review on Biochemical Importance of Vitamin-U" (PDF). Journal of Chemical and Pharmaceutical Research 4 (1): 209–215.
^ 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.
^ Hornsey IS (1999). Brewing. Royal Society of Chemistry. p. 47. ISBN 9780854045686.

External links

Vitamin U at the US National Library of Medicine Medical Subject Headings (MeSH)

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English Journal

A novel automethylation reaction in the Aspergillus nidulans LaeA protein generates S-methylmethionine.

Patananan AN, Palmer JM, Garvey GS, Keller NP, Clarke SG.SourceDepartment of Chemistry and Biochemistry and the Molecular Biology Institute, UCLA, Los Angeles, California 90095, USA.
The Journal of biological chemistry.J Biol Chem.2013 May 17;288(20):14032-45. doi: 10.1074/jbc.M113.465765. Epub 2013 Mar 26.
The filamentous fungi in the genus Aspergillus are opportunistic plant and animal pathogens that can adapt to their environment by producing various secondary metabolites, including lovastatin, penicillin, and aflatoxin. The synthesis of these small molecules is dependent on gene clusters that are g
PMID 23532849

Comparison of GC-MS and NMR for metabolite profiling of rice subjected to submergence stress.

Barding GA Jr, Béni S, Fukao T, Bailey-Serres J, Larive CK.SourceDepartment of Chemistry, University of California-Riverside, Riverside, California 92521, USA.
Journal of proteome research.J Proteome Res.2013 Feb 1;12(2):898-909. doi: 10.1021/pr300953k. Epub 2012 Dec 27.
Natural disasters such as drought, extreme temperatures, and flooding can severely impact crop production. Understanding the metabolic response of crops threatened with these disasters provides insights into biological response mechanisms that can influence survival. In this study, a comparative ana
PMID 23205590

Effects of vitamin U (S-methyl methionine sulphonium chloride) on valproic acid induced liver injury in rats.

Sokmen BB, Tunali S, Yanardag R.SourceDepartment of Chemistry, Faculty of Arts and Sciences, Giresun University, 28049 Giresun, Turkey. baharsokmen@yahoo.com
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2012 Oct;50(10):3562-6. doi: 10.1016/j.fct.2012.07.056. Epub 2012 Aug 4.
In this study, we aimed to investigate the effects of vitamin U (Vit U) on valproic acid (VPA)-induced liver damage. Female Sprague Dawley rats were randomly divided into four groups. Group I was intact control animals. Group II was control rats given Vit U (50 mg/kg/day) for fifteen days. Group III
PMID 22889891

Japanese Journal

胃粘膜傷害における胃・十二指腸ムチンの量的・質的変動に対するメチルメチオニンスルホニウムクロライド(MMSC)後投与の効果

伊東祐子,岡田諭起,三枝陽一,岩井知久,市川尊文,五艘行信,池澤智明,石原和彦
潰瘍 = Ulcer research 35(2), 126-131, 2008-12-25
NAID 10025371302

Dimethyl-.BETA.-Propiothetin, New Potent Resistive-Agent against Stress-Induced Gastric Ulcers in Rats.

NAKAJIMA Kenji
Ｊｏｕｒｎａｌ　ｏｆ　Ｎｕｔｒｉｔｉｏｎａｌ　Ｓｃｉｅｎｃｅ　ａｎｄ　Ｖｉｔａｍｉｎｏｌｏｇｙ　 37(3), 229-238, 1991
… The preventive effect of dimethyl-β-propiothetin (DMPT) and methylmethionine at 5 mM each on stress-induced gastric ulcers in rats was compared. … The ulcer index of test rats in the DMPT group was noticeably lower, compared with those in the methylmethionine and the control groups. …
NAID 130001369185

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★リンクテーブル★

リンク元	「メチルメチオニンスルホニウムクロリド」「メチルメチオニン」「塩化メチルメチオニンスルホニウムクロライド」「MMSC」
関連記事	「methylmethionine」「methylmethionine sulfonium」「chloride」

「メチルメチオニンスルホニウムクロリド」

S-Methylmethionine^[1]
Names
	IUPAC name (3-Amino-3-carboxy-propyl)-dimethyl-sulfonium
	Other names S-Methyl-L-methionine; Vitamin U
Identifiers
CAS Number	4727-40-6
ChEBI	CHEBI:17728
ChemSpider	128519
Jmol 3D model	Interactive image
KEGG	C03172
PubChem	145692
	InChI InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1/t5-/m0/s1 Key: YDBYJHTYSHBBAU-YFKPBYRVSA-O ; InChI=1/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1/t5-/m0/s1 Key: YDBYJHTYSHBBAU-YJIVXYNWBY ;
	SMILES C[S+](C)CC[C@@H](C(=O)O)N ;
Properties
Chemical formula	C6H15NO2S+
Molar mass	164.247 g/mol
Melting point	139 °C (282 °F; 412 K) (bromide salt, decomposes); 134 °C (273 °F) (chloride salt, decomposes)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2760 mg/kg (iv, mice, chloride salt)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: methylmethionine sulfonium chloride, MMSC
同: 塩化メチルメチオニンスルホニウム
商: キャベジンU、ビタスU
関: メチルメチオニン、塩化メチルメチオニンスルホニウムクロライド、ビタミンU

「メチルメチオニン」

　　[★]

英: methylmethionine、methylmethionine sulfonium chloride
関: 塩化メチルメチオニンスルホニウムクロライド、メチルメチオニンスルホニウムクロリド

「塩化メチルメチオニンスルホニウムクロライド」

　　[★]

英: methylmethionine sulfonium chloride
関: メチルメチオニン、メチルメチオニンスルホニウムクロリド

「MMSC」

　　[★]

メチルメチオニンスルホニウムクロリド methylmethionine sulfonium chloride

「methylmethionine」

　　[★]

メチルメチオニン

関: methylmethionine sulfonium chloride

「methylmethionine sulfonium」

　　[★] メチルメチオニンスルホニウム

「chloride」

　　[★] 塩素イオン　　　

[Merck-1] Merck Index, 12th ed., 10165 ISBN 0-911910-12-3

[Bourgis-2] 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.

[ontology-3] National Center for Biomedical Ontology. "Methylmethionine Sulfonium Chloride".

[pmid15436263-4] 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.

[Patel_Prajapati_2012-5] 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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案内

methylmethionine sulfonium chloride