ArticleChembiochem : a European journal of chemical biology2016
Phospha-Michael Addition as a New Click Reaction for Protein Functionalization.
Article in Chembiochem : a European journal of chemical biology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 40 citations in OpenAlex.
- Aza-Michael Quaternization: Addition of Tertiary Amines to Allenic Michael Acceptors Furnishes Quaternary Ammonium Compounds.JACS Au · 2026Article
- Advancing Genetically Encoded Lysine (GEK) Chemistry: From Precision Modulation to Therapeutic Innovation.Accounts of chemical research · 2025Review
- Not So Bioorthogonal Chemistry.Journal of the American Chemical Society · 2025Review
- 2-Cyanopyrimidine-Containing Molecules for N-Terminal Selective Cyclization of Phage-Displayed Peptides.ACS chemical biology · 2025Article
- Diversification of Phage-Displayed Peptide Libraries with Noncanonical Amino Acid Mutagenesis and Chemical Modification.Chemical reviews · 2024Review
- Chemical reaction networks based on conjugate additions on β'-substituted Michael acceptors.Chemical communications (Cambridge, England) · 2023Review
- An Advanced 'clickECM' That Can be Modified by the Inverse-Electron-Demand Diels-Alder Reaction.Chembiochem : a European journal of chemical biology · 2022Article
- A Chemosensor Based on Gold Nanoparticles and Dithiothreitol (DTT) for Acrylamide Electroanalysis.Nanomaterials (Basel, Switzerland) · 2021Article
- Bioorthogonal Reactions of Triarylphosphines and Related Analogues.Chemical reviews · 2021Review
- Bioorthogonal chemistry.Nature reviews. Methods primers · 2021Article
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
- A Genetically Encoded, Phage-Displayed Cyclic-Peptide Library.Angewandte Chemie (International ed. in English) · 2019Review
- Genetically encoding new bioreactivity.New biotechnology · 2017Review
- Site-Selective Modification of Proteins with Oxetanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- The Myeloablative Drug Busulfan Converts Cysteine to Dehydroalanine and Lanthionine in Redoxins.Biochemistry · 2016Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
A new type of click reaction between an alkyl phosphine and acrylamide was developed and applied for site-specific protein labeling in vitro and in live cells. Acrylamide is a small electrophilic olefin that readily undergoes phospha-Michael addition with an alkyl phosphine. Our kinetic study indicated a second-order rate constant of 0.07 m(-1) s(-1) for the reaction between tris(2-carboxyethyl)phosphine and acrylamide at pH 7.4. To demonstrate its application in protein functionalization, we used a dansyl-phosphine conjugate to successfully label proteins that were site-specifically installed with N(ɛ) -acryloyl-l-lysine and employed a biotin-phosphine conjugate to selectively probe human proteins that were metabolically labeled with N-acryloyl-galactosamine.
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Registered trials
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