Water-Soluble Iridium Photoredox Catalyst for the Trifluoromethylation of Biomolecule Substrates in Phosphate Buffered Saline Solvent

Terrence-Thang H Nguyen; Connor J O'Brien; Minh L N Tran; Steven H Olson; Nicholas S Settineri; Stanley B Prusiner; Nick A Paras; Jay Conrad

doi:10.1021/acs.orglett.1c00871

Water-Soluble Iridium Photoredox Catalyst for the Trifluoromethylation of Biomolecule Substrates in Phosphate Buffered Saline Solvent

Org Lett. 2021 May 21;23(10):3823-3827. doi: 10.1021/acs.orglett.1c00871. Epub 2021 Apr 30.

Authors

Terrence-Thang H Nguyen¹, Connor J O'Brien¹, Minh L N Tran¹, Steven H Olson^{1

2}, Nicholas S Settineri³, Stanley B Prusiner^{1

2

4}, Nick A Paras^{1

2}, Jay Conrad^{1

2}

Affiliations

¹ Institute for Neurodegenerative Diseases (IND), Weill Institute for Neurosciences, University of California San Francisco, San Francisco, California 94158, United States.
² Department of Neurology, Weill Institute for Neurosciences, University of California San Francisco, San Francisco, California 94158, United States.
³ Department of Chemistry, University of California Berkeley, Berkeley, California 94720, United States.
⁴ Department of Biochemistry and Biophysics, University of California San Francisco, San Francisco, California 94158, United States.

PMID: 33929208
DOI: 10.1021/acs.orglett.1c00871

Abstract

The development of a water-soluble iridium catalyst enables the trifluoromethylation of polar small molecules and peptides in DMSO solution or aqueous media. The reaction was optimized in a microtiter plate format under ambient air, using commercial Langlois reagent as a CF₃ radical source, blue LEDs for excitation, and using DPBS as solvent to provide up to 60% CF₃- peptide.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrocarbons, Fluorinated / chemistry*
Iridium / chemistry*
Light
Mesylates / chemistry*
Molecular Structure
Phosphates / chemistry*
Solvents*
Water

Substances

Hydrocarbons, Fluorinated
Mesylates
Phosphates
Solvents
sodium trifluoromethanesulfinate
Water
Iridium