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3‐Acyloxyl‐2‐oxopropyl ethers of umbelliferone were investigated as new fluorogenic substrates for lipases and esterases. The aliphatic primary alcohol‐leaving group released the fluorescent product umbelliferone by an enolization/β‐elimination reaction similar to the triose phosphate isomerase (TIM) reaction. A similarly designed phenylacetamide provided a fluorescent probe for penicillin G acylase, whereby the enolization/β‐elimination sequence from the intermediate aminoketone was very fast and spontaneous even under acidic conditions. The corresponding epoxyketone was not fluorogenic with epoxide hydrolases (EH). These substrates represent periodate‐free Clips‐o™ substrates.
Biotechnology Journal – Wiley
Published: Feb 1, 2007
Keywords: ; ; ; ;
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