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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

Benzyl carbamate, 99%

Sigma-Aldrich

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

Sigma-Aldrich

HATU, ≥98.0% (CHN)

Sigma-Aldrich

Sodium carbonate decahydrate, 99.999% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

Copper(I) bromide, 99.999% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

HATU, 97%

Sigma-Aldrich

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

Sigma-Aldrich

Acetic acid, ≥99.5%, FCC, FG

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Supelco

Sodium ascorbate, Pharmaceutical Secondary Standard; Certified Reference Material

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Acetic acid-¹²C₂, 99.9 atom % ¹²C

Sodium ascorbate, European Pharmacopoeia (EP) Reference Standard

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Acetic acid, natural, ≥99.5%, FG

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Acetic acid solution, suitable for HPLC

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

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Acetic acid, glacial, ACS reagent, ≥99.7%

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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%

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

Sigma-Aldrich

Copper(I) bromide, 98%

Sigma-Aldrich

Acetic acid, glacial, ≥99.99% trace metals basis

Sigma-Aldrich

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

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Lithium bromide solution, 54 wt. % in H₂O

Sigma-Aldrich

Magnesium sulfate, ≥99.99% trace metals basis