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Synthesis 2020; 52(21): 3189-3210
DOI: 10.1055/s-0040-1706296
special topic
Recent Advances in Amide Bond Formation

OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

Srinivasa Rao Manne
a   Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Westville, Durban 4000, South Africa   Email: Albericio@ukzn.ac.za
,
Beatriz G. de la Torre
a   Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Westville, Durban 4000, South Africa   Email: Albericio@ukzn.ac.za
b   KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4041, South Africa
,
Ayman El-Faham∗
c   Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia   Email: aelfaham@ksu.edu.sa
d   Department of Chemistry, Faculty of Science, Alexandria University,, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
,
Fernando Albericio∗
a   Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Westville, Durban 4000, South Africa   Email: Albericio@ukzn.ac.za
c   Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia   Email: aelfaham@ksu.edu.sa
e   Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain
f   CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, and Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Spain
› Author AffiliationsWe 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).
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Abstract

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

Key words

coupling reagent - peptides - racemization - amide bonds - solid-phase synthesis


Publication History

Received: 15 July 2020

Accepted after revision: 27 August 2020

Article published online:
30 September 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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