An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes

Despite the great advances in solid-phase peptide synthesis (SPPS), the incorporation of certain functional groups into peptide sequences is restricted by the compatibility of the building blocks with conditions used during SPPS. In particular, the introduction of highly reactive groups used in mode...

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Autores principales:	La Venia, Agustina, Dzijak, Rastislav, Rampmaier, Robert, Vrabel, Milan
Formato:	article artículo
Lenguaje:	Inglés
Publicado:	John Wiley and Sons Inc 2022
Materias:	Bioorthogonal reactions Click chemistry Peptides Solid-phase synthesis Strained dienophiles
Acceso en línea:	http://hdl.handle.net/2133/23309 http://hdl.handle.net/2133/23309
Aporte de:	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario

id	I15-R121-2133-23309
record_format	dspace
institution	Universidad Nacional de Rosario
institution_str	I-15
repository_str	R-121
collection	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language	Inglés
orig_language_str_mv	eng
topic	Bioorthogonal reactions Click chemistry Peptides Solid-phase synthesis Strained dienophiles
spellingShingle	Bioorthogonal reactions Click chemistry Peptides Solid-phase synthesis Strained dienophiles La Venia, Agustina Dzijak, Rastislav Rampmaier, Robert Vrabel, Milan An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes
topic_facet	Bioorthogonal reactions Click chemistry Peptides Solid-phase synthesis Strained dienophiles
description	Despite the great advances in solid-phase peptide synthesis (SPPS), the incorporation of certain functional groups into peptide sequences is restricted by the compatibility of the building blocks with conditions used during SPPS. In particular, the introduction of highly reactive groups used in modern bioorthogonal reactions into peptides remains elusive. Here, we present an optimized synthetic protocol enabling installation of two strained dienophiles, trans-cyclooctene (TCO) and bicyclononyne (BCN), into different peptide sequences. The two groups enable fast and modular post-synthetic functionalization of peptides, as we demonstrate in preparation of peptide-peptide and peptidedrug conjugates. Due to the excellent biocompatibility, the click-functionalization of the peptides can be performed directly in live cells. We further show that the introduction of both clickable groups into peptides enables construction of smart, multifunctional probes that can streamline complex chemical biology experiments such as visualization and pulldown of metabolically labeled glycoconjugates. The presented strategy will find utility in construction of peptides for diverse applications, where high reactivity, efficiency and biocompatibility of the modification step is critical.
format	article artículo
author	La Venia, Agustina Dzijak, Rastislav Rampmaier, Robert Vrabel, Milan
author_facet	La Venia, Agustina Dzijak, Rastislav Rampmaier, Robert Vrabel, Milan
author_sort	La Venia, Agustina
title	An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes
title_short	An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes
title_full	An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes
title_fullStr	An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes
title_full_unstemmed	An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes
title_sort	optimized protocol for the synthesis of peptides containing trans-cyclooctene and bicyclononyne dienophiles as useful multifunctional bioorthogonal probes
publisher	John Wiley and Sons Inc
publishDate	2022
url	http://hdl.handle.net/2133/23309 http://hdl.handle.net/2133/23309
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bdutipo_str	Repositorios
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An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes

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