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S-adenosylmethionine Important methyl-donating coenzyme Can also donate methylene groups, amino groups, ribosyl groups and aminopropyl groups Reactivity based on electrophilic nature of atoms surrounding S+ Tetrahydrofolate is another important methyl carrier Also important in initiating reractions by extracting H (i.e. H∙) via 5’deoxyadenosyl radical Important but not well understood class of enzymes – “Radical SAM” enzymes These reactions remind me very much of Vitamin B12-dependent reactions (which are usually rearrangements) Include ribonucleotide reductase Bioinformatics (based in part on C-X-X-X-C-X-X-C motif of unusual 3 Cys-liganded 4Fe4S center) indicates there are liekly hundreds of these proteins Low levels of folate can result in low levels of SAM (or SAMe) since folate is required for homocysteine  methionine Not found in dietary sources (due to instability, I’m pretty sure?), easily synthesized in us (when healthy)

SAM or SAMe SAH

Clinical uses have included: Antidepressant (mechanism unknown) Treatment of neurological disorders (“ “) Antiosteoarthritis (“ “) Fibromyalgia (“ “) Treatment of liver disease Liver disease results in increase in blood methionine, less SAMe (etiology unknown), low levels of glutathione MAT enzyme seems to be involved (methionine adenosyl transferase, see overview) Parenteral and oral SAMe administration results in increased glutathione levels (and decreased methionine levels (?)

The main parts of the “SAMe cycle” Folate-dependent

Vitamin B12 R = -CH3 (methylcobalamin) –CN (cyanocobalamin, stable vitamin form), -Ad (adenosylcobalamin, active coenzyme) Catalyzes rearrangements One example: methylmalonyl CoA mutase, which is important in breakdown of isoleucine, methionine, threonine, and valine as well as odd-chain fatty acids and cholesterol

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