''S''-Methylmethionine (SMM) is a derivative of

methionine Methionine (symbol Met or M) () is an essential amino acid in humans. As the precursor of other amino acids such as cysteine and taurine, versatile compounds such as SAM-e, and the important antioxidant glutathione, methionine plays a critical ro ...

with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

( CH₃)₂S⁺CH₂CH₂CH(NH₃⁺)CO₂⁻. This

cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

is a naturally-occurring intermediate in many biosynthetic pathways owing to the

sulfonium In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion (a " cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula . Together wi ...

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

. It 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 Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...

methionine ''S''-methyltransferase. ''S''-methylmethionine is particularly abundant in plants, being more abundant than methionine. ''S''-Methylmethionine is sometimes referred to as ''vitamin U'', but it is not considered a true

vitamin A vitamin is an organic molecule (or a set of molecules closely related chemically, i.e. vitamers) that is an Nutrient#Essential nutrients, essential micronutrient that an organism needs in small quantities for the proper functioning of its ...

. The term was coined in 1950 by Garnett Cheney for uncharacterized anti-ulcerogenic factors in raw cabbage juice that may help speed healing of

peptic ulcers Peptic ulcer disease (PUD) is a break in the inner lining of the stomach, the first part of the small intestine, or sometimes the lower esophagus. An ulcer in the stomach is called a gastric ulcer, while one in the first part of the intestines i ...

Biosynthesis and biochemical function

''S''-Methylmethionine arises via the

methylation In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These t ...

by ''S''-adenosyl methionine (SAM). The coproduct is ''S''-adenosyl homocysteine. The biological roles of ''S''-methylmethionine are not well understood. Speculated roles include methionine storage, use as a methyl donor, regulation of SAM. A few plants use ''S''-methylmethionine as a precursor to the

osmolyte Osmolytes are low-molecular weight organic compounds that influence the properties of biological fluids. Their primary role is to maintain the integrity of cells by affecting the viscosity, melting point, and ionic strength of the aqueous solution. ...

dimethylsulfoniopropionate Dimethylsulfoniopropionate (DMSP), is an organosulfur compound with the formula (CH3)2S+CH2CH2COO−. This zwitterionic metabolite can be found in marine phytoplankton, seaweeds, and some species of terrestrial and aquatic vascular plants ...

(DMSP). Intermediates include dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.

Beer flavor precursor in barley malt

''S''-Methylmethionine is found in barley and is further created during the malting process. SMM can be subsequently converted to

dimethyl sulfide Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. Dimethyl sulfide is a flammable liquid that boils at and has a characteristic disagreeable odor. It is a component of the smell produced from cook ...

(DMS) during the malt kilning process, causing an undesirable flavor. 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.

References

External links

* {{DEFAULTSORT:Methylmethionine, S- Amino acids Sulfur amino acids Sulfur ions Methylation Sulfonium compounds