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

Professor Spencer Knapp, Zhexun Sun, and Mohannad Abdo describe the synthesis of the N-(2-seleninatoethyl) amide of N-Boc-phenylalanine, serving here as a peptide model, and its click-type reductive coupling reactions under mild protic 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.

Biohybrid –Se–S– Coupling Reactions

Publication: 

Mohannad Abdo, Zhexun Sun, and Spencer Knapp. Molecules 2013, 18, 1963-1972; doi:10.3390/molecules18021963.

Related:

Mohannad Abdo and Spencer Knapp. Mechanism of a Redox Coupling of Seleninic Acid with Thiol J. Org. Chem., 2012, 77, 3433.

Mohannad Abdo and Spencer Knapp. “Biomimetic Seleninates and Selenonates J. Am. Chem. Soc. 2008, 130, 9234.

Group Members: 
Spencer Knapp Mohannad Abdo Zhexun Sun
Spencer Knapp Mohannad Abdo Zhexun Sun
Year of Research Highlight: 
2013