ArticleChembiochem : a European journal of chemical biology2015
Micelle-Enhanced Bioorthogonal Labeling of Genetically Encoded Azido Groups on the Lipid-Embedded Surface of a GPCR.
Article in Chembiochem : a European journal of chemical biology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 22 citations in OpenAlex.
- Bioorthogonal Chemistry in Biomolecule Quantification: A Review of Reactions and Strategies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Noncanonical Amino Acid Tools and Their Application to Membrane Protein Studies.Chemical reviews · 2024Review
- Addition of LauryldimethylamineACS omega · 2022Article
- FRET sensors reveal the retinal entry pathway in the G protein-coupled receptor rhodopsin.iScience · 2022Article
- Genetic Incorporation of Two Mutually Orthogonal Bioorthogonal Amino Acids That Enable Efficient Protein Dual-Labeling in Cells.ACS chemical biology · 2021Article
- A Strategic Approach for Fluorescence Imaging of Membrane Proteins in a Native-like Environment.Cell chemical biology · 2020Article
- Using genetically incorporated unnatural amino acids to control protein functions in mammalian cells.Essays in biochemistry · 2019Review
- The Energetics of Chromophore Binding in the Visual Photoreceptor Rhodopsin.Biophysical journal · 2017Article
- Site-Specific Bioorthogonal Labeling for Fluorescence Imaging of Intracellular Proteins in Living Cells.Journal of the American Chemical Society · 2016Article
- A simple method for enhancing the bioorthogonality of cyclooctyne reagent.Chemical communications (Cambridge, England) · 2016Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Genetically encoded p-azido-phenylalanine (azF) residues in G protein-coupled receptors (GPCRs) can be targeted with dibenzocyclooctyne-modified (DIBO-modified) fluorescent probes by means of strain-promoted [3+2] azide-alkyne cycloaddition (SpAAC). Here we show that azF residues situated on the transmembrane surfaces of detergent-solubilized receptors exhibit up to 1000-fold rate enhancement relative to azF residues on water-exposed surfaces. We show that the amphipathic moment of the labeling reagent, consisting of hydrophobic DIBO coupled to hydrophilic Alexa dye, results in strong partitioning of the DIBO group into the hydrocarbon core of the detergent micelle and consequently high local reactant concentrations. The observed rate constant for the micelleenhanced SpAAC is comparable with those of the fastest bioorthogonal labeling reactions known. Targeting hydrophobic regions of membrane proteins by use of micelle-enhanced SpAAC should expand the utility of bioorthogonal labeling strategies.
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