Biohybrid -Se-S- Coupling Reactions of an Amino Acid Derived Seleninate

Abstract

We describe the synthesis of the N-(2-seleninatoethyl) amide of N-Boc-phenylalanine, serving here as a peptide model, and its reductive coupling reactions under mild conditions with unprotected thiouridine and glutathione. Selenosulfide products such as these comprise reversibly conjugated bio-components, and can potentially find uses as probes of biological function, such as enzyme inhibitors, delivery systems, or structural mimics.

Keywords

• click reaction
• biomimetic
• seleninic acid
• thiol