OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

OxymaPure [ethyl 2-cyano-2-(hydroxyimino)acetate] is an exceptional reagent with which to suppress racemization and enhance coupling efficiency during amide bond formation. The tremendous popularity of OxymaPure has led to the development of several Oxyma-based reagents. OxymaPure and its derived re...

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Authors: Manne, Srinivasa Rao, de la Torre, Beatriz G., El-Faham, Ayman, Albericio, Fernando
Format: article
Status:Versión aceptada para publicación
Publication Date:2020
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/239272
Online Access:http://hdl.handle.net/10261/239272
Access Level:Open access
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spelling OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide SynthesisManne, Srinivasa Raode la Torre, Beatriz G.El-Faham, AymanAlbericio, FernandoOxymaPure [ethyl 2-cyano-2-(hydroxyimino)acetate] is an exceptional reagent with which to suppress racemization and enhance coupling efficiency during amide bond formation. The tremendous popularity of OxymaPure has led to the development of several Oxyma-based reagents. OxymaPure and its derived reagents are widely used in solid- and solution-phase peptide chemistry. This review summarizes the recent developments and applications of OxymaPure and Oxyma-based reagents in peptide chemistry, in particular in solution-phase chemistry. Moreover, the side reaction associated with OxymaPure is also discussed. 1 Introduction 2 Oxyma-Based Coupling Reagents 2.1 Aminium/Uronium Salts of OxymaPure 2.2 Phosphonium Salts of OxymaPure 2.3 Oxyma-Based Phosphates 2.4 Sulfonate Esters of OxymaPure 2.5 Benzoate Esters of OxymaPure 2.6 Carbonates of OxymaPure Derivatives 3 OxymaPure Derivatives 4 Other Oxime-Based Additives and Coupling Reagents 5 Side Reactions Using OxymaPure Derivatives 6 Conclusion 7 List of Abbreviations.We are grateful to the American Chemical Society (ACS) Green Chemistry Institute (GCI) (Pharmaceutical Roundtable Ignition Grant) for funding S.R.M. In addition, the work in laboratory of the authors was funded in part by the following: the South African Agency for Science and Technology Advancement, The National Research Foundation (NRF) (Blue Sky’s Research Programme, Grant No. 120386) and the University of KwaZulu-Natal (South Africa); the Ministerio de Ciencia e Innovación (Spanish Ministry of Science, Innovation) (RTI2018-093831-B-100), the Departament d’Innovació, Universitats i Empresa, Generalitat de Catalunya (2017 SGR 1439) and the Ministerio de Economía y Competitividad; and the International Scientific Partnership Program ISPP at King Saud University, Saudi Arabia, Riyadh (ISPP# 0061).Georg Thieme VerlagConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2021202120202021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/239272reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1055/s-0040-1706296Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2392722026-05-22T06:33:51Z
dc.title.none.fl_str_mv OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
title OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
spellingShingle OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
Manne, Srinivasa Rao
title_short OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
title_full OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
title_fullStr OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
title_full_unstemmed OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
title_sort OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
dc.creator.none.fl_str_mv Manne, Srinivasa Rao
de la Torre, Beatriz G.
El-Faham, Ayman
Albericio, Fernando
author Manne, Srinivasa Rao
author_facet Manne, Srinivasa Rao
de la Torre, Beatriz G.
El-Faham, Ayman
Albericio, Fernando
author_role author
author2 de la Torre, Beatriz G.
El-Faham, Ayman
Albericio, Fernando
author2_role author
author
author
dc.contributor.none.fl_str_mv Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description OxymaPure [ethyl 2-cyano-2-(hydroxyimino)acetate] is an exceptional reagent with which to suppress racemization and enhance coupling efficiency during amide bond formation. The tremendous popularity of OxymaPure has led to the development of several Oxyma-based reagents. OxymaPure and its derived reagents are widely used in solid- and solution-phase peptide chemistry. This review summarizes the recent developments and applications of OxymaPure and Oxyma-based reagents in peptide chemistry, in particular in solution-phase chemistry. Moreover, the side reaction associated with OxymaPure is also discussed. 1 Introduction 2 Oxyma-Based Coupling Reagents 2.1 Aminium/Uronium Salts of OxymaPure 2.2 Phosphonium Salts of OxymaPure 2.3 Oxyma-Based Phosphates 2.4 Sulfonate Esters of OxymaPure 2.5 Benzoate Esters of OxymaPure 2.6 Carbonates of OxymaPure Derivatives 3 OxymaPure Derivatives 4 Other Oxime-Based Additives and Coupling Reagents 5 Side Reactions Using OxymaPure Derivatives 6 Conclusion 7 List of Abbreviations.
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
2021
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/10261/239272
url http://hdl.handle.net/10261/239272
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1055/s-0040-1706296
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Georg Thieme Verlag
publisher.none.fl_str_mv Georg Thieme Verlag
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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