L-methionine (R)-S-oxide

L-methionine (R)-S-oxide is the R-diastereomer of methionine sulfoxide, an oxidized derivative of the essential amino acid methionine. It is a small molecule and belongs to the class of L-alpha-amino acids. This compound arises through oxidation of methionine residues in proteins by reactive oxygen species, resulting in a mixture of S and R diastereomers. In biological systems, it serves as a metabolite found in or produced by Escherichia coli and yeast[1][6][7]. The reduction back to methionine is catalyzed by specific enzymes such as methionine sulfoxide reductase B for the R-form[5][6]. Methionine sulfoxides are not incorporated into proteins during translation but can accumulate under oxidative stress conditions and may serve as markers for oxidative damage or aging[5]. Experimentally, it has been studied as an inhibitor of amyloid-beta precursor protein[2].

Other names

(2S)-2-amino-4-[(R)-methylsulfinyl]butanoic acidCHEBI:49032(2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid(2S)-2-amino-4-((R)-methanesulfinyl)butanoic acid