 Methylthioadenosine

Methylthioadenosine is a sulfur-containing nucleoside, commonly called 5′-methylthioadenosine. Relative to adenosine, its terminal 5′ hydroxyl group is replaced by $-\mathrm{S}-\mathrm{C}{\mathrm{H}}_3$, a thioether group. Its formula is ${\mathrm{C}}_{11}{\mathrm{H}}_{15}{\mathrm{N}}_5{\mathrm{O}}_3\mathrm{S}$.^[ref]

In plant Ethylene biosynthesis, cleavage of S-adenosylmethionine produces 1-aminocyclopropane-1-carboxylate and methylthioadenosine. The fragments follow different subsequent reactions: the cyclic intermediate supplies Ethylene, whereas the sulfur-containing fragment can be recycled. In 1979, feeding differently labelled methionine to apple tissue connected the sulfur/methyl-labelled portion to a sulfur-containing sugar product, helping distinguish the two routes.^[ref]