Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method

Abstract

Mosher amides of α-methylselenocysteine were synthesized to determine the absolute stereochemistry of the sterically hindered α-carbon utilizing 1H, 13C, 19F, and 77Se NMR spectroscopies. After analysis of these spectra using the established Mosher method, the stereochemistry of the α-carbon was determined to be (R), which was subsequently confirmed using x-ray crystallography.

Keywords

• Unnatural amino acids
• Mosher analysis
• NMR
• Determination of stereochemistry