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Updated: Oct 10, 2026

Simultaneous Quantification of Selected Kynurenines Analyzed by Liquid Chromatography-Mass Spectrometry in Medium Collected from Cancer Cell Cultures
Published on: May 9, 2020
Oxidation of tryptophan to N-formylkynurenine in peptides
Amanda L Moore1, Haram Oh1, Julia E Gulledge1
1Department of Chemistry, University of Richmond, Richmond, VA 23173, USA. cshugrue@richmond.edu.
Abstract:
We report a new method to synthesize N-formylkynurenine (Nfk)-containing peptides. Nfk is a known product of Trp metabolism; yet access to peptides containing this residue remains challenging. Tryptophan (Trp) within peptides can be oxidized to Nfk using sodium periodate (NaIO4) at room temperature in 24 h. This reaction is chemoselective for Trp, and we have demonstrated its compatibility on thirteen peptides with all natural amino acids, except Cys and Met. Nfk residues within peptides could be hydrolysed to kynurenine (Kyn) with 1% TFA in water. Overall, this report presents a mild and selective reaction for generating Nfk in peptide sequences after SPPS.
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