Abstract
Synthesis of indoles labeled with13C-1H and13C-19F spin pairs is described. All syntheses utilize inexpensive carbon-13C dioxide as the13C isotope source. Ruthenium-mediated ring-closing metathesis is the key step in construction of the13C containing indole carbocycle. Fluorine is introducedviaelectrophilic fluorination at the 7-position andviapalladium-mediated cross-coupling at the 4-position. Indole and fluoroindoles are viable tryptophan precursors forin vivoprotein expression. We show that they are viable also inin vitroprotein synthesis using standardE. coliS30 extracts. Incorporation of the synthesized13C-1H and13C-19F spin pair labeled tryptophans into proteins enables high-resolution and high-sensitivity nuclear magnetic resonance (NMR) spectroscopy.
Original language | English |
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Pages (from-to) | 5133-5147 |
Number of pages | 15 |
Journal | Organic and Biomolecular Chemistry |
Volume | 19 |
Issue number | 23 |
DOIs | |
Publication status | Published - 21 Jun 2021 |