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Mixed alkyl aryl phosphonate esters as quenched fluorescent activity-based probes for serine proteases.

Mixed alkyl aryl phosphonate esters as quenched fluorescent activity-based probes for serine proteases.

Organic & biomolecular chemistry (2015-01-03)

Sevnur Serim, Philipp Baer, Steven H L Verhelst

RESUMEN

Activity-based probes (ABPs) are powerful tools for the analysis of active enzyme species in whole proteomes, cells or animals. Quenched fluorescent ABPs (qABPs) can be applied for real time imaging, allowing the visualization of dynamic enzyme activation by fluorescent microscopy. Unfortunately, qABPs are only available for a few enzymes. We here describe the design and synthesis of qABPs for serine proteases based on a phosphonate ester scaffold.

MATERIALES

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Ácido acético, glacial, ACS reagent, ≥99.7%

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Ácido acético, glacial, ReagentPlus^®, ≥99%

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Sulfato de magnesio, anhydrous, ReagentPlus^®, ≥99.5%

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2-Butanona, ACS reagent, ≥99.0%

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Ácido acético, glacial, ≥99.99% trace metals basis

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Bromuro de litio, ReagentPlus^®, ≥99%

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Ácido acético solution, suitable for HPLC

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(+)-Sodium L-ascorbate, crystalline, ≥98%

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(+)-Sodium L-ascorbate, BioXtra, ≥99.0% (NT)

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Dicarbonato de di-terc-butilo, ReagentPlus^®, 99%

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HATU, 97%

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(+)-Sodium L-ascorbate, powder, BioReagent, suitable for cell culture

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Sulfato de magnesio, anhydrous, free-flowing, Redi-Dri^™, ReagentPlus^®, ≥99.5%

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Sulfato de magnesio, BioReagent, suitable for cell culture, suitable for insect cell culture

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Sodium carbonate decahydrate, puriss. p.a., ≥99.0% (T)

Sigma-Aldrich

Copper(I) bromide, 98%

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Bromuro de litio, anhydrous, free-flowing, Redi-Dri^™, ReagentPlus^®, ≥99%

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Sulfato de magnesio, puriss. p.a., drying agent, anhydrous, ≥98.0% (KT), powder (very fine)

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Ácido acético, for luminescence, BioUltra, ≥99.5% (GC)

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Magnesium sulfate solution, for molecular biology, 1.00 M±0.04 M

USP

Ácido acético, United States Pharmacopeia (USP) Reference Standard

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Ácido acético, ≥99.5%, FCC, FG

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Acetyl chloride, reagent grade, 98%

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Sulfato de magnesio, anhydrous, free-flowing, Redi-Dri^™, reagent grade, ≥97%

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Tyramine, ≥98.0%

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Ácido acético, natural, ≥99.5%, FG

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5α-Androstan-17β-ol-3-one, ≥97.5%

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Dicarbonato de di-terc-butilo, ReagentPlus^®, ≥99%

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Magnesium sulfate solution, BioUltra, for molecular biology

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2-Butanona, FCC, FG