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

作者: Gottfried Otting , Ansis Maleckis , Iresha D. Herath

DOI: 10.1039/D1OB00611H

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摘要: 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 key step in construction containing indole carbocycle. Fluorine introduced via electrophilic fluorination at 7-position palladium-mediated cross-coupling 4-position. Indole fluoroindoles are viable tryptophan precursors for vivo protein expression. We show that they also vitro synthesis using standard E. coli S30 extracts. Incorporation synthesized pair tryptophans into proteins enables high-resolution high-sensitivity nuclear magnetic resonance (NMR) spectroscopy.

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