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Fluorogenic substrates for lipases, esterases, and acylases using a TIM‐mechanism for signal release

Fluorogenic substrates for lipases, esterases, and acylases using a TIM‐mechanism for signal release 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Biotechnology Journal Wiley

Fluorogenic substrates for lipases, esterases, and acylases using a TIM‐mechanism for signal release

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References (40)

Publisher
Wiley
Copyright
Copyright © 2007 Wiley Subscription Services, Inc., A Wiley Company
ISSN
1860-6768
eISSN
1860-7314
DOI
10.1002/biot.200600181
pmid
17219461
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Biotechnology JournalWiley

Published: Feb 1, 2007

Keywords: ; ; ; ;

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