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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

HATU, ≥98.0% (CHN)

Sigma-Aldrich

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

Supelco

Acetic acid, analytical standard

Sigma-Aldrich

Acetic acid, glacial, ACS reagent, ≥99.7%

Sigma-Aldrich

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

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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, ≥99.99% trace metals basis

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Lithium bromide solution, 54 wt. % in H₂O

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

Sodium ascorbate, European Pharmacopoeia (EP) Reference Standard

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HATU, 97%

Sigma-Aldrich

Acetic acid, ≥99.5%, FCC, FG

Sigma-Aldrich

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

Sigma-Aldrich

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

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Acetic acid, natural, ≥99.5%, FG

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Acetic acid, SAJ first grade, ≥99.0%

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Acetic acid, ≥99.7%

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Acetic acid, JIS special grade, ≥99.7%

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Acetic acid, 99.5-100.0%

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(+)-Sodium L-ascorbate, SAJ special grade, ≥99.0%

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Acetic acid, ≥99.7%, for titration in non-aqueous medium

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Acetic acid, ≥99.7%, SAJ super special grade

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Acetic acid solution, 1 M, 1 N

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Acetic acid solution, SAJ first grade, 27.0-33.0%

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Acetic acid-¹²C₂, 99.9 atom % ¹²C

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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