Fluorinated Analogues to the Pentuloses of the Pentose Phosphate Pathway
Abstract: Fluorinated carbohydrates are valuable tools for enzymological studies due to their increased metabolic stability compared to their non‐fluorinated analogues. Replacing different hydroxyl groups within the same monosaccharide by fluorine allows to influence a wide range of sugar–receptor interactions and enzymatic transformations. In the past, this principle was frequently used to study the metabolism of highly abundant carbohydrates, while the metabolic fate of rare sugars is still poorly studied. Rare sugars, however, are key intermediates of many metabolic routes, such as the pentose phosphate pathway (PPP). Here we present the design and purely chemical synthesis of a set of three deoxyfluorinated analogues of the rare sugars d‐xylulose and d‐ribulose: 1‐deoxy‐1‐fluoro‐d‐ribulose (1DFRu), 3‐deoxy‐3‐fluoro‐d‐ribulose (3DFRu) and 3‐deoxy‐3‐fluoro‐d‐xylulose (3DFXu). Together with a designed set of potential late‐stage radio‐fluorination precursors, they have the potential to become useful tools for studies on the complex equilibria of the non‐oxidative PPP.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Fluorinated Analogues to the Pentuloses of the Pentose Phosphate Pathway ; day:02 ; month:06 ; year:2023 ; extent:7
European journal of organic chemistry ; (02.06.2023) (gesamt 7)
- Creator
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Scheibelberger, Lukas
Stankovic, Toda
Liepert, Kaja
Kienzle, Andreas
Patronas, Eva‐Maria
Balber, Theresa
Mitterhauser, Markus
Haschemi, Arvand
Pallitsch, Katharina
- DOI
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10.1002/ejoc.202300339
- URN
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urn:nbn:de:101:1-2023060315104302178886
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:58 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Scheibelberger, Lukas
- Stankovic, Toda
- Liepert, Kaja
- Kienzle, Andreas
- Patronas, Eva‐Maria
- Balber, Theresa
- Mitterhauser, Markus
- Haschemi, Arvand
- Pallitsch, Katharina
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Solid‐Phase Synthesis of Fluorinated Analogues of Glycosyl 1‐Phosphate Repeating Structures from Leishmania using the Phosphoramidite Method
Inflammation, glucose, and vascular cell damage: the role of the pentose phosphate pathway
The pentose phosphate pathway in industrially relevant fungi: crucial insights for bioprocessing
Two high-rate pentose-phosphate pathways in cancer cells
Lactylation stabilizes DCBLD1 activating the pentose phosphate pathway to promote cervical cancer progression
Progesterone increases metabolism via the pentose phosphate pathway in bovine uterine epithelial cells
Targeting pentose phosphate pathway for SARS-CoV-2 therapy
Erratum to: Inflammation, glucose, and vascular cell damage: the role of the pentose phosphate pathway
Data mining of the transcriptome of Plasmodium falciparum: the pentose phosphate pathway and ancillary processes
Regulation of the pentose phosphate pathway in cancer
The pentose phosphate pathway regulates chronic neuroinflammation and dopaminergic neurodegeneration
Targeting the pentose phosphate pathway for SARS-CoV-2 therapy
Solid‐Phase Synthesis of Fluorinated Analogues of Glycosyl 1‐Phosphate Repeating Structures from Leishmania using the Phosphoramidite Method
Inflammation, glucose, and vascular cell damage: the role of the pentose phosphate pathway
The pentose phosphate pathway in industrially relevant fungi: crucial insights for bioprocessing
Two high-rate pentose-phosphate pathways in cancer cells
Lactylation stabilizes DCBLD1 activating the pentose phosphate pathway to promote cervical cancer progression
Progesterone increases metabolism via the pentose phosphate pathway in bovine uterine epithelial cells
Targeting pentose phosphate pathway for SARS-CoV-2 therapy
Erratum to: Inflammation, glucose, and vascular cell damage: the role of the pentose phosphate pathway