<div class="csl-bib-body">
<div class="csl-entry">Scheibelreiter, V., Kalaus, H., & Stanetty, C. (2024, June 30). <i>F-labelled 2-aminobenzamidoximes as Aldehyde-Selective Probes for 19f-nmr Based Qualitative Analysis of Aldoses</i> [Poster Presentation]. 18th Belgian Organic Synthesis Symposium, Liege, Belgium. https://doi.org/10.34726/7404</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/204842
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dc.identifier.uri
https://doi.org/10.34726/7404
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dc.description.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, so they constitute a class of complex chiral aldehydes. 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) [1]. 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 to ensure a fast reaction. Furthermore, 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 all aldopentoses and aldohexoses for this derivative. An impressive influence of the stereochemistry up to 9 bonds apart from the fluorine atom on its chemical shift was observed, underlining the potential of F-labelled aminobenzamidoximes as probes for other types of aldehyde-mixtures within and beyond the sugar realm.
en
dc.description.sponsorship
FWF - Österr. Wissenschaftsfonds
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dc.language.iso
en
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dc.rights.uri
http://creativecommons.org/licenses/by/4.0/
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dc.subject
Carbohydrate analysis
en
dc.subject
sugar
en
dc.title
F-labelled 2-aminobenzamidoximes as Aldehyde-Selective Probes for 19f-nmr Based Qualitative Analysis of Aldoses
en
dc.type
Presentation
en
dc.type
Vortrag
de
dc.rights.license
Creative Commons Namensnennung 4.0 International
de
dc.rights.license
Creative Commons Attribution 4.0 International
en
dc.identifier.doi
10.34726/7404
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dc.relation.grantno
P 29138-N34
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dc.type.category
Poster Presentation
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tuw.project.title
Kontrollierter Zuckerabbau durch N-Heterocyclische Carbene
