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 -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, PA14 strain.
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