Synthesis of redox-active fluorinated 5-hydroxytryptophans as molecular reporters for biological electron transfer

Amanda Ohler; Hanna Long; Kei Ohgo; Kristin Tyson; David Murray; Amanda Davis; Chris Whittington; Eli G. Hvastkovs; Liam Duffy; Alice Haddy; Andrew L. Sargent; William E. Allen; Adam R. Offenbacher

doi:10.1039/D1CC00187F

Synthesis of redox-active fluorinated 5-hydroxytryptophans as molecular reporters for biological electron transfer†

Amanda Ohler,‡^a Hanna Long,‡^a Kei Ohgo,^a Kristin Tyson,^a David Murray,^a Amanda Davis,^a Chris Whittington,^a Eli G. Hvastkovs,^a Liam Duffy,^b Alice Haddy,^b Andrew L. Sargent,^a William E. Allen^a and Adam R. Offenbacher

*^a

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^a Department of Chemistry, East Carolina University, Greenville, NC, USA
E-mail: offenbachera17@ecu.edu

^b Department of Chemistry and Biochemistry, University of North Carolina, Greensboro, NC, USA

Abstract

Fluorinated 5-hydroxytryptophans (F_n-5HOWs) were synthesized in gram scale quantities and incorporated into a β-hairpin peptide and the protein azurin. The redox-active F_n-5HOWs exhibit unique radical spectroscopic signatures that expand the function of 5HOW as probes for biological electron transfer.

Chemical Communications

Synthesis of redox-active fluorinated 5-hydroxytryptophans as molecular reporters for biological electron transfer†

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Synthesis of redox-active fluorinated 5-hydroxytryptophans as molecular reporters for biological electron transfer

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