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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

ABSTRACT

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.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Acetic acid, for luminescence, BioUltra, ≥99.5% (GC)

Supelco

Acetic acid, analytical standard

Sigma-Aldrich

Di-tert-butyl dicarbonate, ≥98.0% (GC)

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Di-tert-butyl dicarbonate, ReagentPlus^®, 99%

Sigma-Aldrich

Copper(I) bromide, 99.999% trace metals basis

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Acetic acid, natural, ≥99.5%, FG

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Acetic acid, ≥99.5%, FCC, FG

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Di-tert-butyl dicarbonate, ReagentPlus^®, ≥99%

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Benzyl carbamate, 99%

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

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

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Sodium carbonate decahydrate, 99.999% trace metals basis

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Copper(I) bromide, AnhydroBeads^™, -10 mesh, 99.99% trace metals basis

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Acetic acid-¹²C₂, 99.9 atom % ¹²C

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Sodium ascorbate, Pharmaceutical Secondary Standard; Certified Reference Material

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Acetic acid solution, suitable for HPLC

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Acetic acid, glacial, ACS reagent, ≥99.7%

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Acetic acid, glacial, puriss., meets analytical specification of Ph. Eur., BP, USP, FCC, 99.8-100.5%

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Acetic acid, glacial, ≥99.99% trace metals basis

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Acetic acid, glacial, ReagentPlus^®, ≥99%

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Acetic acid, glacial, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8%

Sodium ascorbate, European Pharmacopoeia (EP) Reference Standard

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2-Butanone, ACS reagent, ≥99.0%

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

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2-Butanone, ReagentPlus^®, ≥99%

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Copper(I) bromide, 98%

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Lithium bromide solution, 54 wt. % in H₂O

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2-Butanone, ACS reagent, ≥99.0%