An optimized protocol for the synthesis of peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as useful multifunctional bioorthogonal probes

dc.creatorLa Venia, Agustina
dc.creatorDzijak, Rastislav
dc.creatorRampmaier, Robert
dc.creatorVrabel, Milan
dc.date2022-04-01T16:51:59Z
dc.date2022-04-01T16:51:59Z
dc.date2021-09-24
dc.date2022-04-01T16:51:59Z
dc.date2022-04-01T16:51:59Z
dc.date2021-09-24
dc.identifier1521-3765
dc.identifierhttp://hdl.handle.net/2133/23309
dc.identifierhttp://hdl.handle.net/2133/23309
dc.descriptionDespite 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.
dc.descriptionFil: La Venia, Agustina. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; Czech Republic.
dc.descriptionFil: La Venia, Agustina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.
dc.descriptionFil: Dzijak, Rastislav. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; Czech Republic.
dc.descriptionFil: Rampmaier, Robert. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; Czech Republic.
dc.descriptionFil: Vrabel, Milan. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; Czech Republic.
dc.formatapplication/pdf
dc.languageeng
dc.publisherJohn Wiley and Sons Inc
dc.relationhttps://doi.org/10.1002/chem.202102042
dc.relationhttps://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202102042
dc.rightsJohn Wiley and Sons Inc
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
dc.rightsopenAccess
dc.subjectBioorthogonal reactions
dc.subjectClick chemistry
dc.subjectPeptides
dc.subjectSolid-phase synthesis
dc.subjectStrained dienophiles
dc.titleAn optimized protocol for the synthesis of peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as useful multifunctional bioorthogonal probes
dc.typepublishedVersion
dc.typearticle
dc.typeartículo


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