Abstract
Continuing our studies on the formation of tryptophan-derived glycoconjugates, we observed that the reactivity of tryptophan was significantly higher towards D-ribose in comparison to D-glucose. Detailed analysis of the reaction products obtained from tryptophan and the pentose sugars D-ribose, D-xylose, and L-arabinose by means of HPLC-mass spectrometry revealed the formation of several C-glycosyl derivatives, N-glycosides, glyco-tetrahydro-β-carbolines, and of carbohydrate-derived β-carbolines. Following the isolation of these compounds from model reactions, the structure elucidation was accomplished by NMR spectroscopy. Finally, we proved the presence of these novel tryptophan derivatives in various food samples by HPLC-MS analysis.
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