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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

Supelco

Acetic acid, analytical standard

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Acetic acid, ≥99.5%, FCC, FG

Sigma-Aldrich

Acetic acid, natural, ≥99.5%, FG

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Acetic acid-¹²C₂, 99.9 atom % ¹²C

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Sodium carbonate decahydrate, 99.999% trace metals basis

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Copper(I) bromide, 99.999% trace metals basis

Sigma-Aldrich

Benzyl carbamate, 99%

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

Sigma-Aldrich

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

Supelco

Sodium ascorbate, Pharmaceutical Secondary Standard; Certified Reference Material

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

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HATU, ≥98.0% (CHN)

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HATU, 97%

Sigma-Aldrich

Acetic acid solution, suitable for HPLC

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

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

Sigma-Aldrich

Acetic acid, glacial, puriss., 99-100%

Sigma-Aldrich

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

Sigma-Aldrich

Copper(I) bromide, 98%

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Acetic acid, glacial, ACS reagent, ≥99.7%

Sodium ascorbate, European Pharmacopoeia (EP) Reference Standard

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Lithium bromide solution, 54 wt. % in H₂O

Sigma-Aldrich

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

Sigma-Aldrich

Acetic acid, glacial, ≥99.99% trace metals basis

Sigma-Aldrich

Tyramine, 98%, FG