Evaluation of Pseudoenantiomeric Mixed Carbonates as Efficient Fluorogenic Probes for Enantioselectivity Screening

Żądło, Anna; Koszelewski, Dominik; Borys, Filip; Ostaszewski, Ryszard

doi:10.1002/cbic.201500509

Cited by 5 publications

(2 citation statements)

References 41 publications

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“…Previously, we developed a mixed carbonate-based assay as a new class of fluorogenic probes for screening the activity and stereoselectivity of lipases and esterases. 17,18 These substrates showed high specific reactivity with enzymes and acceptable stability against nonspecific degradation, which make them substrates for high-throughput screening. Moreover, coumarins bearing a cargo via a carbonate linkage might be successfully applied for the cellular uptake of peptides, 19 as thiol probes for bioimaging, 20 or as probes for the detection of lysine-targeting enzymes.…”

Section: Introductionmentioning

confidence: 99%

Self-immolative versatile fluorogenic probes for screening of hydrolytic enzyme activity

et al. 2016

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Enzyme triggered probes with a self-immolative linker for rapid and sensitive hydrolase detection through a cascade reaction have been reported. Their utility was proved by the preparation of three model compounds and their evaluation as enzyme substrates and demonstration of their applicability as fluorogenic probes for screening lipase, esterase and protease activities. These probes represent a new class of fluorogenic compounds, are stable under aqueous conditions and not susceptible to nonspecific degradation. The utilization of the carbamate cleavable linkage in a probe structure allows moving away of the bulky fluorophore from the enzyme recognition unit and targets different classes of enzymes with the same substrate.

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Section: Introductionmentioning

confidence: 99%

Self-immolative versatile fluorogenic probes for screening of hydrolytic enzyme activity

et al. 2016

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“…22 This versatility contributes to their biotechnological application in industrial settings, where molecular engineering techniques, coupled with green chemistry processes, allow the production of high value-added inputs. 23,24 As such, demand for these new biocatalysts requires rapid and sensitive methodologies to evaluate enzymatic activities, 2,5,16,25 conversion, enantioselectivity (E) 9,14,26 and enantiomeric excess (ee). 3 Thus, spectrophotometric methods that use chromogenic 27 or fluorogenic 7,16,25 substrates as sensors are ideal for monitoring enzymatic activities.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Multienzymatic Screening with Fluorogenic Probes

Lima

Chaves

Nascimento

et al. 2017

J. Braz. Chem. Soc.

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The simultaneous screening of multiple enzyme activities in a single assay has numerous advantages over the traditional format, since it decreases sampling errors, allows savings in reagents and consumables and reduces the time and labor required to conduct the assays. In the present study, a direct and sensitive assay for the simultaneous detection of epoxide hydrolase and esterase (or lipase) activities was developed. Signal overlap is avoided by synthesizing fluorogenic probes with enzyme-specific alkyl linkers, connected to different fluorophores (resorfurin and umbelliferone), which exhibit emission spectra at different wavelengths. The simultaneous assays were conducted in microplate format with the fluorogenic probes monitored in the same well that uses microorganisms as enzyme source. Our results show that the fluorescent signal from each of the probes used here can be discriminated, allowing multiple enzyme activity detection and quantitation.

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Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

et al. 2020

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6‐O‐Glucose‐4‐phenylbutyrate was used successfully as promoting aqueous reaction medium for the synthesis of fourteen different α‐acyloxy carboxamides with the biologically relevant coumarin scaffold. Two different one‐pot protocols; chemical and chemoenzymatic, based on the usage of biodegradable surfactants for the synthesis of target products were developed. The chemoenzymatic method consists of 3‐steps in which the first step is oxidation catalyzed by Trametes versicolor laccase/O2, followed by spontaneous condensation reaction, and finally multicomponent Passerini reaction. All transformations occurred at room temperature in the same reaction vials without isolation of the reaction intermediates. The influence of the reaction conditions including substrate structure on the reaction course was studied. The application of an aqueous solution of 6‐O‐glucose 4‐phenylbutyrate as the reaction medium had the pivotal impact of the reaction rate providing target α‐acyloxy carboxamides with the yields up to 65 %. Obtained peptidomimetics were characterized by UV‐VIS and fluorescence spectroscopy.

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Evaluation of Pseudoenantiomeric Mixed Carbonates as Efficient Fluorogenic Probes for Enantioselectivity Screening

Cited by 5 publications

References 41 publications

Self-immolative versatile fluorogenic probes for screening of hydrolytic enzyme activity

Self-immolative versatile fluorogenic probes for screening of hydrolytic enzyme activity

Simultaneous Multienzymatic Screening with Fluorogenic Probes

Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

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