Scheibelreiter, V., Kalaus, H., & Stanetty, C. (2023, July 11). Utilizing Fluorine-labelled 2-Aminobenzamidoximes to Distinguish Aldoses via 19F-NMR [Poster Presentation]. 21st European Carbohydrate Symposium (Eurocarb21) 2023, Paris, France. https://doi.org/10.34726/5314
21st European Carbohydrate Symposium (Eurocarb21) 2023
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Event date:
9-Jul-2023 - 13-Jul-2023
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Event place:
Paris, France
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Keywords:
Carbohydrate analysis; 19F-NMR
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Abstract:
Aldoses are structurally composed of a reactive aldehyde group and multiple hydroxy groups. Each specific sugar exhibits a defined stereochemistry of these alcoholic moieties. Being constitutional isomers, the differentiation between sugars, especially in mixtures, is challenging. Previously, we have described a photometric kinetic assay to determine the open-chain content of aldoses utilizing the selective reaction with 2-aminobenzamidoxime (ABAO). Herein, we have taken further advantage of this aldehyde-selective reaction, using it for a qualitative aldose assay based on 19F-NMR, a highly sensitive and fast method. The influence of the position of the F-label on the adduct formation rates was determined and derivatives of selected aldoses were prepared and the deviation of chemical shifts in 19F-NMR of the products were compared. While all four tested F-ABAO derivatives showed differences in shifts between the tested aldoses, one derivative was especially promising for the application in a qualitative sugar assay and the scope was expanded to a larger set of aldoses for this derivative.
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Research facilities:
Zentrum für Kernspinresonanzspektroskopie
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Project title:
Kontrollierter Zuckerabbau durch N-Heterocyclische Carbene: P 29138-N34 (FWF - Österr. Wissenschaftsfonds)