ArticleBioconjugate chemistry2018
On-Resin Macrocyclization of Peptides Using Vinyl Sulfonamides as a Thiol-Michael "Click" Acceptor.
Article in Bioconjugate chemistry, 2018. 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.
- Organometallic Chemistry Approach to Peptide Tricycles.Bioconjugate chemistry · 2026Article
- From Eyes to Cameras to Kinetics: Computer Vision for Chemical Process Monitoring.Accounts of chemical research · 2026Article
- A Sydnonimine-based Click-and-Release Approach to Cyclic Products.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Hydrolytically Stable Maleimide-End-Functionalized Polymers for Site-Specific Protein Conjugation.Bioconjugate chemistry · 2021Article
- Covalent and Noncovalent Targeting of the Tcf4/β-Catenin Strand Interface with β-Hairpin Mimics.ACS chemical biology · 2021Article
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- Expanding the Thiol-X Toolbox: Photoinitiation and Materials Application of the Acid-Catalyzed Thiol-ene (ACT) Reaction.Polymer chemistry · 2021Article
- Photochemical Methods for Peptide Macrocyclisation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Sequence-defined vinyl sulfonamide click nucleic acids (VS-CNAs) and their assembly into dynamically responsive materials.Chemical communications (Cambridge, England) · 2020Article
- Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides.Beilstein journal of organic chemistry · 2019Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Macrocyclization of linear peptides imparts improved stability to enzymatic degradation and increases potency of function. Many successful macrocyclization of peptides both in solution and on-resin have been achieved but are limited in scope as they lack selectivity, require long reaction times, or necessitate heat. To overcome these drawbacks a robust and facile strategy was developed employing thiol-Michael click chemistry via an N-methyl vinyl sulfonamide. We demonstrate its balance of reactivity and high stability through FTIR model kinetic studies, reaching 88% conversion over 30 min, and NMR stability studies, revealing no apparent degradation over an 8 day period in basic conditions. Using a commercially available reagent, 2-chloroethane sulfonyl chloride, the cell adhesion peptide, RGDS, was functionalized and macrocyclized on-resin with a relative efficiency of over 95%. The simplistic nature of this process demonstrates the effectiveness of vinyl sulfonamides as a thiol-Michael click acceptor and its applicability to many other bioconjugation applications.
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Registered trials
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