Synthesis of13C/19F/2H labeled indoles for use as tryptophan precursors for protein NMR spectroscopy

Ansis Maleckis*, Iresha D. Herath, Gottfried Otting

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    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 languageEnglish
    Pages (from-to)5133-5147
    Number of pages15
    JournalOrganic and Biomolecular Chemistry
    Volume19
    Issue number23
    DOIs
    Publication statusPublished - 21 Jun 2021

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