Issue 13, 2025

PIDA-mediated synthesis of kynurenine derivatives by oxidative fragmentation of the tryptophan scaffold

Abstract

Kynurenine metabolites are derived from the aromatic amino acid, tryptophan, and their chemical synthesis has been sought to understand the tryptophan–kynurenine-based biochemical reactions that could provide opportunities for exploring therapeutic values. This report describes the synthesis of kynurenine (kyn) derivatives from tryptophan-containing peptides using the versatile hypervalent iodine reagent, phenyliodine(III)diacetate (PIDA), through the C–C bond fragmentation of tryptophan's indole ring. However, BocNH-Trp-OH and N-arylated (both benzenoid and non-benzenoid) tryptophan derivatives produce unique spirocyclic molecules with PIDA under similar reaction conditions. In screening for therapeutic values, the sequence-specific kynurenine derivatives show inhibition of quorum sensing against multidrug-resistant pathogenic bacteria, Pseudomonas aeruginosa PA14 strain.

Graphical abstract: PIDA-mediated synthesis of kynurenine derivatives by oxidative fragmentation of the tryptophan scaffold

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Article information

Article type
Paper
Submitted
13 Jan 2025
Accepted
24 Feb 2025
First published
25 Feb 2025

Org. Biomol. Chem., 2025,23, 3208-3223

PIDA-mediated synthesis of kynurenine derivatives by oxidative fragmentation of the tryptophan scaffold

C. K. Jena, A. Patnaik, S. S. Nayak, S. Kumari, A. Panda, M. Dixit and N. K. Sharma, Org. Biomol. Chem., 2025, 23, 3208 DOI: 10.1039/D5OB00057B

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