Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis

Amidation is the predominant reaction within the pharmaceutical setting, and it is attracting greater attention due to the increased demand for therapeutic peptides. The high therapeutic efficacy and safety profile of peptides have placed these molecules in prime position within the pharmaceutical a...

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Autores: Al Musaimi, Othman, Wisdom, Richard, Talbiersky, Peter, De La Torre, Beatriz G., Albericio, Fernando
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2021
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/266789
Acceso en línea:http://hdl.handle.net/10261/266789
https://api.elsevier.com/content/abstract/scopus_id/85100888688
Access Level:acceso abierto
Palabra clave:T3P ®
Amidation
Green chemistry
Peptides
SPPS
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spelling Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide SynthesisAl Musaimi, OthmanWisdom, RichardTalbiersky, PeterDe La Torre, Beatriz G.Albericio, FernandoT3P ®AmidationGreen chemistryPeptidesSPPSAmidation is the predominant reaction within the pharmaceutical setting, and it is attracting greater attention due to the increased demand for therapeutic peptides. The high therapeutic efficacy and safety profile of peptides have placed these molecules in prime position within the pharmaceutical arena, which is reflected by these molecules receiving several approvals from various regulatory agencies each year. In this context, the demand for developing efficient strategies for peptide synthesis has also risen. Although propylphosphonic anhydride (T3P®), which has been recently proposed as a green coupling reagent, has shown good performance in solution, it has never been applied to solid-phase peptide synthesis (SPPS). Here we test the use of T3P® for SPPS. Satisfactory yields were achieved with a mild activation protocol. Various green solvents were tested and proved to be compatible with this coupling reagent. Several commonly used reagents cause allergic reactions or are susceptible to explosion under certain conditions. To overcome these issues, we propose T3P® as a potential alternative coupling reagent in SPPS.The work was funded in part by the following: the National Research Foundation (NRF) (#105892 and Blue Sky's Research Programme #120386) and the University of KwaZulu-Natal (South Africa); and the Spanish Ministry of Science, Innovation, and Universities (RTI2018-093831-B-100) and the Generalitat de Catalunya (2017 SGR 1439) (Spain).Peer reviewedWiley-Blackwell0000-0002-8946-0462Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202220222021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/266789https://api.elsevier.com/content/abstract/scopus_id/85100888688reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)InglésChemistrySelecthttps://doi.org/10.1002/slct.202100123Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2667892026-05-22T06:33:51Z
dc.title.none.fl_str_mv Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
title Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
spellingShingle Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
Al Musaimi, Othman
T3P ®
Amidation
Green chemistry
Peptides
SPPS
title_short Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
title_full Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
title_fullStr Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
title_full_unstemmed Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
title_sort Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid-Phase Peptide Synthesis
dc.creator.none.fl_str_mv Al Musaimi, Othman
Wisdom, Richard
Talbiersky, Peter
De La Torre, Beatriz G.
Albericio, Fernando
author Al Musaimi, Othman
author_facet Al Musaimi, Othman
Wisdom, Richard
Talbiersky, Peter
De La Torre, Beatriz G.
Albericio, Fernando
author_role author
author2 Wisdom, Richard
Talbiersky, Peter
De La Torre, Beatriz G.
Albericio, Fernando
author2_role author
author
author
author
dc.contributor.none.fl_str_mv 0000-0002-8946-0462
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv T3P ®
Amidation
Green chemistry
Peptides
SPPS
topic T3P ®
Amidation
Green chemistry
Peptides
SPPS
description Amidation is the predominant reaction within the pharmaceutical setting, and it is attracting greater attention due to the increased demand for therapeutic peptides. The high therapeutic efficacy and safety profile of peptides have placed these molecules in prime position within the pharmaceutical arena, which is reflected by these molecules receiving several approvals from various regulatory agencies each year. In this context, the demand for developing efficient strategies for peptide synthesis has also risen. Although propylphosphonic anhydride (T3P®), which has been recently proposed as a green coupling reagent, has shown good performance in solution, it has never been applied to solid-phase peptide synthesis (SPPS). Here we test the use of T3P® for SPPS. Satisfactory yields were achieved with a mild activation protocol. Various green solvents were tested and proved to be compatible with this coupling reagent. Several commonly used reagents cause allergic reactions or are susceptible to explosion under certain conditions. To overcome these issues, we propose T3P® as a potential alternative coupling reagent in SPPS.
publishDate 2021
dc.date.none.fl_str_mv 2021
2022
2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/266789
https://api.elsevier.com/content/abstract/scopus_id/85100888688
url http://hdl.handle.net/10261/266789
https://api.elsevier.com/content/abstract/scopus_id/85100888688
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv ChemistrySelect
https://doi.org/10.1002/slct.202100123
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-Blackwell
publisher.none.fl_str_mv Wiley-Blackwell
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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