NDLI: Mechanisms of chemical protein <sup>19</sup>F-labeling and NMR-based biosensor construction <i>in vitro</i> and in cells using self-assembling ligand-directed tosylate compounds

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Stable singlet carbenes as mimics for transition metal centers

Excited states and optical absorption of small semiconducting clusters: Dopants, defects and charging

Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of benzoxazecinones

Ordered metal nanostructure self-assembly using metal–organic frameworks as templates

Universal characteristics of chemical synthesis and property optimization

Highly selective additions of hydride and organolithium nucleophiles to helical carbenium ions

The bigger, the better: Ring-size effects of macrocyclic oligomeric Co(iii)-salen catalysts

Discrimination of flavonoids and red wine varietals by arrays of differential peptidic sensors

Synthesis of boron doped polymeric carbon nitride solids and their use as metal-free catalysts for aliphatic C–H bond oxidation

Metal-binding properties of Hpn from Helicobacter pylori and implications for the therapeutic activity of bismuth

Vinylogous reactivity of silver(i) vinylcarbenoids

The unique nature of H⁺ in water

Dinitrogen complexation with main group radicals

Genetically encoding an aliphatic diazirine for protein photocrosslinking

Sulfonated graphene as water-tolerant solid acid catalyst

Ir-catalyzed highly selective addition of pyridyl C–H bonds to aldehydes promoted by triethylsilane

A dual-functional tetrakis-imidazolium macrocycle for supramolecular assembly

Accelerated bimolecular reactions in microdroplets studied by desorption electrospray ionization mass spectrometry

Mechanisms of chemical protein ¹⁹F-labeling and NMR-based biosensor construction in vitro and in cells using self-assembling ligand-directed tosylate compounds

Synthesis and utility of fluorogenic acetoxymethyl ethers

Tailoring Au-core Pd-shell Pt-cluster nanoparticles for enhanced electrocatalytic activity

Unprecedented encapsulation of a [Fe^IIICl₄]⁻ anion in a cationic [Fe^II₄L₆]⁸⁺ tetrahedral cage derived from 5,5′′′-dimethyl-2,2′:5′,5′′:2′′,2′′′-quaterpyridine

Ru-catalyzed activation of sp³ C–O bonds: O- to N-alkyl migratory rearrangement in pyridines and related heterocycles

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Chemical Science Vol - 2 Issue - 2

Chemical Science Vol -1

Mechanisms of chemical protein ¹⁹F-labeling and NMR-based biosensor construction in vitro and in cells using self-assembling ligand-directed tosylate compounds

Content Provider	Royal Society of Chemistry (RSC)
Author	Hamachi, Itaru Sun, Yedi Takaoka, Yousuke Tsukiji, Shinya
Copyright Year	2011
Abstract	Chemical labeling methods that convert a specific endogenous protein into a semisynthetic biosensor offer numerous new opportunities for biological research and drug discovery. We recently developed a novel protein labeling scheme, termed ligand-directed tosyl (LDT) chemistry, which can site-specifically introduce a synthetic probe to a protein with the concomitant release of the affinity ligand. In previous work, we demonstrated that LDT reagent 1 can be used to modify carbonic anhydrase I (CAI) with a 19F probe, converting it into a 19F NMR-based biosensor for CAI inhibitors either in vitro or in red blood cells (RBCs). We herein report the chemical properties of 1, and the mechanisms controlling biosensor construction. It was revealed that the LDT reagent forms self-assembled aggregates in the absence of the target protein. In the aggregated state, nonproductive hydrolysis of the reagent was significantly suppressed, which suggests the potential utility of self-assembly in the design of labeling reagents that have increased stability. In the presence of the target protein, the aggregates were disrupted to form a noncovalent protein–reagent complex, and protein 19F-labeling proceeded to generate 19F-labeled CAI. The ligand-binding pocket of the labeled CAI retained the cleaved ligand fragment in vitro, whereas the pocket was vacant in RBC. Further biochemical studies suggested that an anion transporter might play a role in eliminating the cleaved ligand from the interior to the exterior of the cells. The findings provide a fundamental basis for the rational design of reagents applicable to selective protein labeling and biosensor construction in biological contexts.
Starting Page	511
Ending Page	520
Page Count	10
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	2
Issue Number	3
Journal	Chemical Science
DOI	10.1039/c0sc00513d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Semisynthesis Ligand Ion CAI Reagent Protein Fluorine-19 nuclear magnetic resonance Hydrolysis RBC Self-assembly Carbonic anhydrase Biosensor Tosyl Drug discovery
Content Type	Text
Resource Type	Article
Subject	Chemistry

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One-step construction of caged carbonic anhydrase I using a ligand-directed acyl imidazole-based protein labeling method

Current NMR Techniques for Structure-Based Drug Discovery

New power of self-assembling carbonic anhydrase inhibitor: Short peptide–constructed nanofibers inspire hypoxic cancer therapy

Fluorine NMR studies of the human carbonic anhydrase–3,5-difluorobenzenesulfonamide complex†

15 chapter 2 selection of a multi-ligand capture agent for carbonic anhydrase ii by iterative in situ.

Fluorine-labeling as a diagnostic for thiol-ligand and gold nanocluster self-assembly.

Determination of intracellular protein-ligand binding affinity by competition binding in-cell NMR.

In vitro effects of some anabolic compounds on erythrocyte carbonic anhydrase I and II

Metal complexes of 1,3,4-thiadiazole-2,5-disulfonamide are strong dual carbonic anhydrase inhibitors, although the ligand possesses very weak such properties.

Mechanisms of chemical protein ¹⁹F-labeling and NMR-based biosensor construction in vitro and in cells using self-assembling ligand-directed tosylate compounds

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