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On-resin microwave-assisted copper-catalyzed azide-alkyne cycloaddition of H1-relaxin B single chain 'stapled' analogues
- Source :
- Peptide Science 112 (2020). doi:10.1002/pep2.24159, info:cnr-pdr/source/autori:D'Ercole, Annunziata; Sabatino, Giuseppina; Pacini, Lorenzo; Impresari, Elisa; Capecchi, Ilaria; Papini, Anna Maria; Rovero, Paolo/titolo:On-resin microwave-assisted copper-catalyzed azide-alkyne cycloaddition of H1-relaxin B single chain 'stapled' analogues/doi:10.1002%2Fpep2.24159/rivista:Peptide Science/anno:2020/pagina_da:/pagina_a:/intervallo_pagine:/volume:112
- Publication Year :
- 2020
-
Abstract
- The development of conformationally constrained analogues of bioactive peptides is a relevant goal in peptide medicinal chemistry. Among the several classes of conformationally constrained peptides, the so-called stapled peptides, which bear a side-chain-to-side-chain bridge, are particularly interesting since they offer the possibility to stabilize specific conformational elements, such as a-helices or beta-turns. We describe an efficient and reproducible microwave-assisted strategy to prepare side-chain-to-side-chain clicked peptides, performing the copper-catalyzed azide-alkyne cycloaddition on solid phase, using as a model peptide a portion of the H1-relaxin B chain, which contains the binding cassette motif of this important bioactive peptide. All the relevant parameters, that is, resin, solvent, catalytic system, microwave energy and reaction time were optimized using a systematic one-factor-at-a-time (OFAT) approach. This method will be useful for the preparation of libraries of conformationally constrained relaxin analogues.
- Subjects :
- chemistry.chemical_classification
Relaxin
Chemistry
Organic Chemistry
Biophysics
Alkyne
Single chain
stapled peptides
microwave-assisted click reaction
Biochemistry
Combinatorial chemistry
Microwave assisted
H1-relaxin B chain
on-resin CuAAC
Cycloaddition
Biomaterials
chemistry.chemical_compound
Copper catalyzed
Azide
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Journal :
- Peptide Science 112 (2020). doi:10.1002/pep2.24159, info:cnr-pdr/source/autori:D'Ercole, Annunziata; Sabatino, Giuseppina; Pacini, Lorenzo; Impresari, Elisa; Capecchi, Ilaria; Papini, Anna Maria; Rovero, Paolo/titolo:On-resin microwave-assisted copper-catalyzed azide-alkyne cycloaddition of H1-relaxin B single chain 'stapled' analogues/doi:10.1002%2Fpep2.24159/rivista:Peptide Science/anno:2020/pagina_da:/pagina_a:/intervallo_pagine:/volume:112
- Accession number :
- edsair.doi.dedup.....e365063093ff2ca08bea3ece181a3d1a