| S-Methylmethionine[1] | |
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(3-Amino-3-carboxy-propyl)-dimethyl-sulfonium |
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Other names
S-Methyl-L-methionine |
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| Identifiers | |
| CAS number | 4727-40-6 |
| PubChem | 458 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H15NO2S+ |
| Molar mass | 164.247 g/mol |
| Melting point |
139 °C (282 °F)[1] (bromide salt, decomp.) |
| Hazards | |
| LD50 | 2760 mg/kg (iv, mice, chloride salt)[1] |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
S-Methylmethionine is a derivative of methionine with 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]
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In the radical-SAM enzymes, an iron-sulfur cluster binds and reduces S-adenosylmethionine to generate a methyl radical, which is involved in many hundreds of biosynthetic transformations.[3]
The osmolyte dimethylsulfoniopropionate (DMSP), produced by marine algae, is biosynthesized from S-methylmethionine. Intermediates include dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.[4]
In 1949, cabbage juice was found to significantly increase the rate of healing in patients with gastrointestinal ulceration.[5] Further work showed that these results are attributed to an unknown, heat-sensitive substance, dubbed the unidentified substance(s) responsible for the rapid healing "vitamin U", although this it is not recognized as a vitamin. S-Methylmethionine is sometimes still referred to as vitamin U in naturopathic medicine, but it is not recognized as a vitamin by mainstream nutrition science.