Related Experiment Video
Updated: Aug 14, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation
Joshua A Ritchey1, Bonnie M Davis, Patricia A Pleban
1Department of Chemistry and Biochemistry, Old Dominion University, Hampton Boulevard, Norfolk, VA 23529, USA.
Abstract:
The oxidation products of selenomethionine (SeMet) have been studied via experimental (77)Se NMR and theoretical (77)Se chemical shifts. Four signals are observed: a diastereomeric pair of selenoxides at 840 ppm and two unidentified resonances at 703 and 716 ppm. Theoretical DeltaG and chemical shifts suggest the 703 and 716 ppm resonances correspond to hypervalent selenium heterocycles, called selenuranes, formed by reaction with the amine or acid group of the amino acid and the selenoxide. To identify which of these selenuranes is formed, the amine and acid groups were individually protected. The N-formyl SeMet formed only the selenoxide pair at 840 ppm. The oxidized SeMet methyl ester produced signals at 703 and 716 ppm which are assigned as the Se-N selenurane.
Related Concept Videos
Preparation and Reactions of Sulfides
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Sulfur Assimilation
Preparation and Reactions of Thiols
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Phase II Reactions: Glutathione Conjugation and Mercapturic Acid Formation
Several distinctive characteristics distinguish glutathione conjugation from other phase II...
