The Aryne phosphate reaction
Abstract: Condensed phosphates are a critically important class of molecules in biochemistry, with a myriad of derived structures being known. Moreover, non-natural analogues are important for various applications, such as single molecule real time DNA sequencing. Often, such analogues contain more than three phosphate units in their oligophosphate chain. Consequently, investigations into phosphate reactivity enabling new ways of phosphate functionalization and oligophosphorylation are an essential endeavour in the field. Here, we scrutinize the potential of phosphates to act as arynophiles, paving the way for follow-up oligophosphorylation reactions. The aryne phosphate reaction is a powerful tool to – depending on the perspective – (oligo)phosphorylate arenes or arylate (oligo-cyclo)phosphates. Based on Kobayashi-type o-silylaryltriflates, the aryne phosphate reaction enables rapid entry into a broad spectrum of arylated products, like monophosphates, diphosphates, phosphodiesters and polyphosphates. The synthetic potential of these new transformations is demonstrated by efficient syntheses of nucleotide analogues and an unprecedented one-flask octaphosphorylation
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Event
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Veröffentlichung
- (where)
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Freiburg
- (who)
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Universität
- (when)
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2024
- Creator
- DOI
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10.26434/chemrxiv-2021-3mfj8
- URN
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urn:nbn:de:bsz:25-freidok-2463087
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:45 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Haas, Thomas Michael
- Wiesler, Stefan
- Dürr-Mayer, Tobias
- Ripp, Alexander
- Fouka, Paraskevi
- Qiu, Danye
- Jessen, Henning Jacob
- Universität
Time of origin
- 2024
Other Objects (12)
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Untersuchungen zur intrazellulären Freisetzung von Nucleosidphosphaten
The aryne phosphate reaction**
The aryne phosphate reaction
The inositol hexakisphosphate kinases IP6K1 and -2 regulate human cellular phosphate homeostasis, including XPR1-mediated phosphate export
The Aryne Phosphate Reaction **
The Aryne Phosphate Reaction **
Metabolic consequences of polyphosphate synthesis and imminent phosphate limitation
Development of novel p-amidites and their application in the synthesis of the most densely phosphorylated compounds
The 8th young faculty meeting – an active crowd attuned to modern challenges
Investigations on the synthesis and degradation of polyphosphate in vitro and its correlation to magic spot nucleotides
Synthesis of bisdiphosphoinositol polyphosphate prometabolites
Novel shades of inositol pyrophosphates – in vitro and in cellulo evaluation of inositol pyrophosphate probes
Untersuchungen zur intrazellulären Freisetzung von Nucleosidphosphaten
The aryne phosphate reaction**
The aryne phosphate reaction
The inositol hexakisphosphate kinases IP6K1 and -2 regulate human cellular phosphate homeostasis, including XPR1-mediated phosphate export
The Aryne Phosphate Reaction **
The Aryne Phosphate Reaction **
Metabolic consequences of polyphosphate synthesis and imminent phosphate limitation
Development of novel p-amidites and their application in the synthesis of the most densely phosphorylated compounds
The 8th young faculty meeting – an active crowd attuned to modern challenges
Investigations on the synthesis and degradation of polyphosphate in vitro and its correlation to magic spot nucleotides
Synthesis of bisdiphosphoinositol polyphosphate prometabolites