S-Methylmethionine
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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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| 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.
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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.