Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2023 |
| Outros Autores: | , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| Texto Completo: | http://hdl.handle.net/10451/59964 |
Resumo: | © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| id |
RCAP_d9e91083cd1e9efe5c5c80708c2c79a0 |
|---|---|
| oai_identifier_str |
oai:repositorio.ul.pt:10451/59964 |
| network_acronym_str |
RCAP |
| network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| repository_id_str |
7160 |
| spelling |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent processChemical BiologyMulticomponent ReactionsPeptidesTetrazinesUgi Reaction© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.Multicomponent reactions are of utmost importance at generating a unique, wide, and complex chemical space. Herein we describe a novel multicomponent approach based on the combination of the isonitrile-tetrazine (4+1) cycloaddition and the Ugi four-component reaction to generate pyrazole amide derivatives. The scope of the reaction as well as mechanistic insights governing the 4H-pyrazol-4-imine tautomerization are provided. This multicomponent process provides access to a new chemical space of pyrazole amide derivatives and offers a tool for peptide modification and stapling.This work was supported by a Marie Skłodowska-Curie grant (Agreement No. 101018454) from the European Union's Horizon 2020 research and innovation program. We thank the DFG (post-doctoral fellowship, grant no. 493006134, to A. V. V.), Fundação para a Ciência e a Tecnologia (Ph.D. studentship 2022.09827.BD to A. L. D.) and MCIN/AEI/10.13039/501100011033 (PID2021-125946OB-I00 to G. J. O. and CEX2021-001136-S to CIC bioGUNE).WileyRepositório da Universidade de LisboaMéndez, YaniraVasco, Aldrin V.Ivey, GalwayDias, Ana LauraGierth, PeterSousa, Bárbara B.Navo, Claudio D.Torres‐Mozas, AngelRodrigues, TiagoJiménez‐Osés, GonzaloBernardes, Gonçalo J. L.2023-10-25T15:13:30Z20232023-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10451/59964engAngew Chem Int Ed Engl. 2023 Oct 26;62(44):e2023111861433-785110.1002/anie.2023111861521-3773info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-08T17:09:31Zoai:repositorio.ul.pt:10451/59964Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T22:09:48.995198Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
| dc.title.none.fl_str_mv |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process |
| title |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process |
| spellingShingle |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process Méndez, Yanira Chemical Biology Multicomponent Reactions Peptides Tetrazines Ugi Reaction |
| title_short |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process |
| title_full |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process |
| title_fullStr |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process |
| title_full_unstemmed |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process |
| title_sort |
Merging the Isonitrile‐Tetrazine (4+1) cycloaddition and the Ugi four‐component reaction into a single multicomponent process |
| author |
Méndez, Yanira |
| author_facet |
Méndez, Yanira Vasco, Aldrin V. Ivey, Galway Dias, Ana Laura Gierth, Peter Sousa, Bárbara B. Navo, Claudio D. Torres‐Mozas, Angel Rodrigues, Tiago Jiménez‐Osés, Gonzalo Bernardes, Gonçalo J. L. |
| author_role |
author |
| author2 |
Vasco, Aldrin V. Ivey, Galway Dias, Ana Laura Gierth, Peter Sousa, Bárbara B. Navo, Claudio D. Torres‐Mozas, Angel Rodrigues, Tiago Jiménez‐Osés, Gonzalo Bernardes, Gonçalo J. L. |
| author2_role |
author author author author author author author author author author |
| dc.contributor.none.fl_str_mv |
Repositório da Universidade de Lisboa |
| dc.contributor.author.fl_str_mv |
Méndez, Yanira Vasco, Aldrin V. Ivey, Galway Dias, Ana Laura Gierth, Peter Sousa, Bárbara B. Navo, Claudio D. Torres‐Mozas, Angel Rodrigues, Tiago Jiménez‐Osés, Gonzalo Bernardes, Gonçalo J. L. |
| dc.subject.por.fl_str_mv |
Chemical Biology Multicomponent Reactions Peptides Tetrazines Ugi Reaction |
| topic |
Chemical Biology Multicomponent Reactions Peptides Tetrazines Ugi Reaction |
| description |
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| publishDate |
2023 |
| dc.date.none.fl_str_mv |
2023-10-25T15:13:30Z 2023 2023-01-01T00:00:00Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10451/59964 |
| url |
http://hdl.handle.net/10451/59964 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
Angew Chem Int Ed Engl. 2023 Oct 26;62(44):e202311186 1433-7851 10.1002/anie.202311186 1521-3773 |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
| eu_rights_str_mv |
openAccess |
| dc.format.none.fl_str_mv |
application/pdf |
| dc.publisher.none.fl_str_mv |
Wiley |
| publisher.none.fl_str_mv |
Wiley |
| dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
| instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
| instacron_str |
RCAAP |
| institution |
RCAAP |
| reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
| repository.mail.fl_str_mv |
|
| _version_ |
1799134652698460160 |