S-Methylmethionine: Difference between revisions
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== References == |
== References == |
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{{Reflist}} |
{{Reflist}} |
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==Further reading== |
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*{{cite journal |first1=Na Young |last1=Lee |first2=Kui Young |last2=Park |first3=Hye Jung |last3=Min |first4=Kye Yong |last4=Song |first5=Yun Young |last5=Lim |first6=Juhee |last6=Park |first7=Beom Joon |last7=Kim |first8=Myeung Nam |last8=Kim |title=Inhibitory Effect of Vitamin U (S-Methylmethionine Sulfonium Chloride) on Differentiation in 3T3-L1 Pre-adipocyte Cell Lines |journal=Annals of Dermatology |pmid=22363154 |year=2012 |volume=24 |issue=1 |pages=39–44 |doi=10.5021/ad.2012.24.1.39 |pmc=3283849}} |
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*{{cite journal |first1=Xiao-Lin |last1=Jiang |first2=Lee Wah |last2=Lim |first3=Toyohide |last3=Takeuchi |title=Vitamin U-bonded Stationary Phase in Capillary Ion Chromatography |journal=Analytical Sciences |pmid=22156247 |year=2011 |volume=27 |issue=12 |pages=1203–6 |doi=10.2116/analsci.27.1203}} |
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*{{cite journal |doi=10.1159/000276495 |title=Accelerated Wound Healing by ''S''-Methylmethionine Sulfonium: Evidence of Dermal Fibroblast Activation via the ERK1/2 Pathway |year=2010 |last1=Kim |first1=Won-Serk |last2=Yang |first2=You Jin |last3=Min |first3=Hyung Geun |last4=Song |first4=Min Gyu |last5=Lee |first5=Ji-Seon |last6=Park |first6=Keung-Young |last7=Kim |first7=Jin-Ju |last8=Sung |first8=Jong-Hyuk |last9=Choi |first9=Jun-Seok |journal=Pharmacology |volume=85 |issue=2 |pages=68–76 |pmid=20110751}} |
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*{{cite journal |doi=10.1111/j.1440-1746.2008.05667.x |title=Effects of combination treatment with famotidine and methylmethionine sulfonium chloride on the mucus barrier of rat gastric mucosa |year=2009 |last1=Ichikawa |first1=Takafumi |last2=Ito |first2=Yuko |last3=Saegusa |first3=Yoichi |last4=Iwai |first4=Tomohisa |last5=Goso |first5=Yukinobu |last6=Ikezawa |first6=Tomoaki |last7=Ishihara |first7=Kazuhiko |journal=Journal of Gastroenterology and Hepatology |volume=24 |issue=3 |pages=488–92 |pmid=19175830}} |
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*{{cite journal |doi=10.1111/j.1751-0813.2007.00197.x |title=Effect of s-methylmethionine sulphonium chloride on oesophagogastric ulcers in pigs |year=2007 |last1=Kopinski |first1=JS |last2=Fogarty |first2=R |last3=McVeigh |first3=J |journal=Australian Veterinary Journal |volume=85 |issue=9 |pages=362–7 |pmid=17760939}} |
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*{{cite book |first=Ashley Lynn |last=Shaw |year=2007 |title=The efficacy of DL-Methionine methylsulfonium chloride on performance characteristics and intestinal tract integrity in broilers |type=MS Thesis |publisher=Auburn University |url=http://hdl.handle.net/10415/826 |oclc=191697478}} |
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*{{cite journal |doi=10.1136/vr.137.12.290 |title=Effect of hammer mill screen size and addition of fibre or S-methylmethionine-sulphonium chloride to the diet on the occurrence of oesophagogastric lesions in fattening pigs |year=1995 |last1=Elbers |first1=A. |last2=Vos |first2=J. |last3=Hemke |first3=G. |last4=Hunneman |first4=W. |journal=Veterinary Record |volume=137 |issue=12 |pages=290–3 |pmid=8533223}} |
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*{{cite journal |pmid=8443719 |year=1993 |last1=Salim |first1=AS |title=Sulfhydryl-containing agents in the treatment of gastric bleeding induced by nonsteroidal anti-inflammatory drugs |volume=36 |issue=1 |pages=53–8 |journal=Canadian Journal of Surgery}} |
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*{{cite journal |doi=10.1159/000139016 |title=Role of Sulphydryl-Containing Agents in the Management of Recurrent Attacks of Ulcerative Colitis |year=1992 |last1=Salim |first1=Aws S. |journal=Pharmacology |volume=45 |issue=6 |pages=307–18 |pmid=1362613}} |
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*{{cite journal |doi=10.1159/000138995 |title=Sulphydryl-Containing Agents Stimulate the Healing of Duodenal Ulceration in Man |year=1992 |last1=Salim |first1=Aws S. |journal=Pharmacology |volume=45 |issue=3 |pages=170–80 |pmid=1438525}} |
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*{{cite journal |pmid=6234776 |year=1983 |last1=Tamás |first1=J |last2=Bokori |first2=J |last3=Hegedüs |first3=M |title=Oesophagogastric ulcer in swine and vitamin U. I. Relative incidence of the syndrome in Hungary |volume=31 |issue=4 |pages=145–53 |journal=Acta veterinaria Hungarica}} |
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*{{cite journal |pmid=6234777 |year=1983 |last1=Hegedüs |first1=M |last2=Bokori |first2=J |last3=Tamás |first3=J |title=Oesophagogastric ulcer in swine and vitamin U. II. Nature of vitamin U |volume=31 |issue=4 |pages=155–63 |journal=Acta veterinaria Hungarica}} |
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*{{cite journal |pmid=2953195 |year=1986 |last1=Tamás |first1=J |last2=Hegedüs |first2=M |last3=Bokori |first3=J |title=Oesophagogastric ulcer in swine and vitamin U. III. Reduction of economic losses by vitamin U |volume=34 |issue=1–2 |pages=81–92 |journal=Acta veterinaria Hungarica}} |
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*{{cite journal |pmid=2953196 |year=1986 |last1=Tamás |first1=J |last2=Hegedüs |first2=M |last3=Bokori |first3=J |title=Oesophagogastric ulcer in swine and vitamin U. IV. Efficiency of the Hungarian vitamin U preparation in reduction of economic losses |volume=34 |issue=1–2 |pages=93–100 |journal=Acta veterinaria Hungarica}} |
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*{{cite journal |first1=Garnett |last1=Cheney |first2=Samuel H. |last2=Waxler |first3=Ivan J. |last3=Miller |pmid=13276831 |year=1956 |title=Vitamin U Therapy of Peptic Ulcer: Experience at San Quentin Prison |volume=84 |issue=1 |pages=39–42 |pmc=1532869 |journal=California Medicine}} |
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*{{cite journal |first1=Garnett |last1=Cheney |pmid=13009468 |year=1952 |title=Vitamin U therapy of peptic ulcer |volume=77 |issue=4 |pages=248–52 |pmc=1521464 |journal=California medicine}} |
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{{refend}} |
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{{DEFAULTSORT:Methylmethionine, S-}} |
{{DEFAULTSORT:Methylmethionine, S-}} |
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Revision as of 19:49, 23 May 2013
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| Names | |
|---|---|
| IUPAC name
(3-Amino-3-carboxy-propyl)-dimethyl-sulfonium
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| Other names
S-Methyl-L-methionine
Vitamin U | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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|
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| Properties | |
| C6H15NO2S+ | |
| Molar mass | 164.247 g/mol |
| Melting point | 139 °C (282 °F)[1] (bromide salt, decomp.) 134 °C (273 °F)[1] (chloride salt, decomp.) |
| Hazards | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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).
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S-Methylmethionine is a derivative of methionine with the chemical formula [(CH3)3S(CH2)2CHNH3CO2]+. 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]
Biochemical function
The osmolyte dimethylsulfoniopropionate (DMSP), produced by marine algae, is biosynthesized from S-methylmethionine. Intermediates include dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.[3]
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).[4]
References
- ^ a b c d Merck Index, 12th Edition, 10165
- ^ 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.
- ^ McNeil, S. D. (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, Ian S (25 Nov 1999). Brewing. Royal Society of Chemistry. p. 47. ISBN 9780854045686.
{{cite book}}: Cite has empty unknown parameter:|1=(help)
Further reading
- Lee, Na Young; Park, Kui Young; Min, Hye Jung; Song, Kye Yong; Lim, Yun Young; Park, Juhee; Kim, Beom Joon; Kim, Myeung Nam (2012). "Inhibitory Effect of Vitamin U (S-Methylmethionine Sulfonium Chloride) on Differentiation in 3T3-L1 Pre-adipocyte Cell Lines". Annals of Dermatology. 24 (1): 39–44. doi:10.5021/ad.2012.24.1.39. PMC 3283849. PMID 22363154.
- Jiang, Xiao-Lin; Lim, Lee Wah; Takeuchi, Toyohide (2011). "Vitamin U-bonded Stationary Phase in Capillary Ion Chromatography". Analytical Sciences. 27 (12): 1203–6. doi:10.2116/analsci.27.1203. PMID 22156247.
- Kim, Won-Serk; Yang, You Jin; Min, Hyung Geun; Song, Min Gyu; Lee, Ji-Seon; Park, Keung-Young; Kim, Jin-Ju; Sung, Jong-Hyuk; Choi, Jun-Seok (2010). "Accelerated Wound Healing by S-Methylmethionine Sulfonium: Evidence of Dermal Fibroblast Activation via the ERK1/2 Pathway". Pharmacology. 85 (2): 68–76. doi:10.1159/000276495. PMID 20110751.
- Ichikawa, Takafumi; Ito, Yuko; Saegusa, Yoichi; Iwai, Tomohisa; Goso, Yukinobu; Ikezawa, Tomoaki; Ishihara, Kazuhiko (2009). "Effects of combination treatment with famotidine and methylmethionine sulfonium chloride on the mucus barrier of rat gastric mucosa". Journal of Gastroenterology and Hepatology. 24 (3): 488–92. doi:10.1111/j.1440-1746.2008.05667.x. PMID 19175830.
- Kopinski, JS; Fogarty, R; McVeigh, J (2007). "Effect of s-methylmethionine sulphonium chloride on oesophagogastric ulcers in pigs". Australian Veterinary Journal. 85 (9): 362–7. doi:10.1111/j.1751-0813.2007.00197.x. PMID 17760939.
- Shaw, Ashley Lynn (2007). The efficacy of DL-Methionine methylsulfonium chloride on performance characteristics and intestinal tract integrity in broilers (MS Thesis). Auburn University. OCLC 191697478.
- Elbers, A.; Vos, J.; Hemke, G.; Hunneman, W. (1995). "Effect of hammer mill screen size and addition of fibre or S-methylmethionine-sulphonium chloride to the diet on the occurrence of oesophagogastric lesions in fattening pigs". Veterinary Record. 137 (12): 290–3. doi:10.1136/vr.137.12.290. PMID 8533223.
- Salim, AS (1993). "Sulfhydryl-containing agents in the treatment of gastric bleeding induced by nonsteroidal anti-inflammatory drugs". Canadian Journal of Surgery. 36 (1): 53–8. PMID 8443719.
- Salim, Aws S. (1992). "Role of Sulphydryl-Containing Agents in the Management of Recurrent Attacks of Ulcerative Colitis". Pharmacology. 45 (6): 307–18. doi:10.1159/000139016. PMID 1362613.
- Salim, Aws S. (1992). "Sulphydryl-Containing Agents Stimulate the Healing of Duodenal Ulceration in Man". Pharmacology. 45 (3): 170–80. doi:10.1159/000138995. PMID 1438525.
- Tamás, J; Bokori, J; Hegedüs, M (1983). "Oesophagogastric ulcer in swine and vitamin U. I. Relative incidence of the syndrome in Hungary". Acta veterinaria Hungarica. 31 (4): 145–53. PMID 6234776.
- Hegedüs, M; Bokori, J; Tamás, J (1983). "Oesophagogastric ulcer in swine and vitamin U. II. Nature of vitamin U". Acta veterinaria Hungarica. 31 (4): 155–63. PMID 6234777.
- Tamás, J; Hegedüs, M; Bokori, J (1986). "Oesophagogastric ulcer in swine and vitamin U. III. Reduction of economic losses by vitamin U". Acta veterinaria Hungarica. 34 (1–2): 81–92. PMID 2953195.
- Tamás, J; Hegedüs, M; Bokori, J (1986). "Oesophagogastric ulcer in swine and vitamin U. IV. Efficiency of the Hungarian vitamin U preparation in reduction of economic losses". Acta veterinaria Hungarica. 34 (1–2): 93–100. PMID 2953196.
- Cheney, Garnett; Waxler, Samuel H.; Miller, Ivan J. (1956). "Vitamin U Therapy of Peptic Ulcer: Experience at San Quentin Prison". California Medicine. 84 (1): 39–42. PMC 1532869. PMID 13276831.
- Cheney, Garnett (1952). "Vitamin U therapy of peptic ulcer". California medicine. 77 (4): 248–52. PMC 1521464. PMID 13009468.