OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis,Synthesis

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OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
Synthesis ( IF 2.2 ) Pub Date : 2020-09-30 , DOI: 10.1055/s-0040-1706296
Ayman El-Faham _{1,

2} , Fernando Albericio _{1,

3,

4,

5} , Srinivasa Rao Manne ₃ , Beatriz G. de la Torre _{3,

6}

Affiliation

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

Publication History

Received: 15 July 2020

Accepted after revision: 27 August 2020

Publication Date:
30 September 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

OxymaPure偶联试剂：固相肽合成之外

摘要

OxymaPure [2-氰基-2-（羟基亚氨基）乙酸乙酯]是一种特殊的试剂，可用于抑制外消旋作用并提高酰胺键形成过程中的偶联效率。OxymaPure的巨大普及导致开发了几种基于Oxyma的试剂。OxymaPure及其衍生的试剂广泛用于固相和溶液相肽化学。这篇综述总结了OxymaPure和基于Oxyma的试剂在肽化学特别是溶液相化学中的最新发展和应用。此外，还讨论了与OxymaPure相关的副反应。

1引言

2种基于氧的偶联试剂

2.1 OxymaPure的铵/铀盐

2.2 OxymaPure的os盐

2.3基于氧的磷酸盐

2.4 OxymaPure的磺酸酯

2.5 OxymaPure的苯甲酸酯

2.6 OxymaPure衍生物的碳酸盐

3种OxymaPure衍生物

4其他基于肟的添加剂和偶联剂

使用OxymaPure衍生物的5种副反应

六，结论