New Monofunctionalized Fluorescein Derivatives for the Efficient High-Throughput Screening of Lipases and Esterases in Aqueous Media
✍ Scribed by Yongzheng Yang; Peter Babiak; Jean-Louis Reymond
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- German
- Weight
- 317 KB
- Volume
- 89
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Monoalkylation or acylation of fluorescein (1) with various acyloxymethyl or acyl halides afforded, respectively, a series of ether‐ (2) and ester‐functionalized (3) fluorogenic probes. The highly reactive and water‐soluble substrates release fluorescein (1) upon reaction with lipases and esterases within seconds or minutes, both under fully aqueous conditions or in the presence of DMSO (20%) as a co‐solvent. The most‐reactive substrates in the two series were the octanoic acid derivatives 2f (= 2‐{6‐[(octanoyloxy)methoxy]‐3‐oxo‐3__H__‐xanthen‐9‐yl}benzoic acid) and 3a (= 2‐[6‐(octanoyloxy)‐3‐oxo‐3__H__‐xanthen‐9‐yl]benzoic acid). Esterases were found to generally react faster under aqueous conditions, while lipases were more reactive in the presence of DMSO as a co‐solvent.