OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

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- A nd 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.