Synthesis of (13)C/(19)F/(2)H labeled indoles for use as tryptophan precursors for protein NMR spectroscopy
 

Synthesis of (13)C/(19)F/(2)H labeled indoles for use as tryptophan precursors for protein NMR spectroscopy

Synthesis of indoles labeled with 13C-1H and 13C-19F spin pairs is described. All syntheses utilize inexpensive carbon-13C dioxide as the 13C isotope source. Ruthenium-mediated ring-closing metathesis is the key step in construction of the 13C containing indole carbocycle. Fluorine is introduced via electrophilic fluorination at the 7-position and via palladium-mediated cross-coupling at the 4-position. Indole and fluoroindoles are viable tryptophan precursors for in vivo protein expression. We...

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