Medizinische Universität Graz Austria/Österreich - Forschungsportal - Medical University of Graz
Gewählte Publikation:
SHR Neuro Krebs Kardio Lipid Stoffw Microb
Leypold, M; Wallace, PW; Kljajic, M; Schittmayer, M; Pletz, J; Illaszewicz-Trattner, C; Guebitz, GM; Birner-Gruenberger, R; Breinbauer, R.
A robust and simple protocol for the synthesis of arylfluorophosphonates
TETRAHEDRON LETT. 2015; 56(41): 5619-5622.
Doi: 10.1016/j.tetlet.2015.08.061
Web of Science
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- Co-Autor*innen der Med Uni Graz
- Birner-Grünberger Ruth
- Schittmayer-Schantl Matthias
- Wallace Pal William
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- Abstract:
- Fluorophosphonates represent powerful probes for the identification and analysis of active serine hydrolases in activity based protein profiling. Although alkylphosphonofluoridates are widely used for such purposes, little is known about the synthesis and purification of arylphosphonofluoridates, which may be useful tools for screening enzyme activities toward aromatic esters. Our optimized route makes this subclass of transition state inhibitors broadly accessible for a diverse series of phosphonic acid derivatives using a combination of selective monoesterification with EDC center dot HCl and subsequent mild fluorination with DAST. All compounds were isolated as pure materials using a simple acid-base extraction protocol in 76-93% yields over two steps. These probes can be stored under an inert atmosphere at -24 degrees C for several months without significant degradation. (C) 2015 Elsevier Ltd. All rights reserved.
- Find related publications in this database (Keywords)
- Arylphosphonofluoridates
- Activity based probes
- Monoesterification
- DAST fluorination
- Pyrophosphonates