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| - Reaction of Tryptophan with Carbohydrates: Mechanistic Studieson the Formation of Carbohydrate-Derived β-Carbolines
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| - Numerous carbohydrate-derived β-carbolines have been identified for the first time in model reactionsof tryptophan with glucose and ribose, as well as in food samples. Extending these structural studies,we performed detailed investigations to elucidate the corresponding intermediates and formationpathway of these alkaloids. Degradation experiments with purified tryptophan glycoconjugatesestablished that only glyco-tetrahydro-β-carboline-3-carboxylic acids, and not the N-glycosides northe C-glycoconjugates represented the direct precursors of carbohydrate-derived β-carbolines. Inaddition, the significance of the oxidative decarboxylation reaction as the initial step for formationof 1-substituted β-carbolines was proven. Finally, the stereochemistry of the carbohydrate-derivedside chain was studied by means of CD spectroscopy and HPLC-CD experiments. These detailedstereochemical analyses yielded experimental evidence for the racemization steps required forformation of the carbohydrate-derived harman alkaloids and confirmed the proposed reactionpathway. Keywords: l-Tryptophan; β-carbolines; Maillard reaction; stereochemistry; HPLC-CD
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