Synthesis 2017; 49(03): 472-483
DOI: 10.1055/s-0036-1588607
short review
© Georg Thieme Verlag Stuttgart · New York

An Overview of the Synthesis of Highly Versatile N-Hydroxysuccinimide Esters

Anaïs Barré
a   Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France
b   VFP Therapies, 15 rue François Couperin, 76000 Rouen, France   Email: cyril.papamicael@insa-rouen.fr   Email: vgembus@vfp-therapies.com
,
Mihaela-Liliana Ţînţaş
a   Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France
,
Vincent Levacher
a   Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France
,
Cyril Papamicaël*
a   Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France
,
Vincent Gembus*
b   VFP Therapies, 15 rue François Couperin, 76000 Rouen, France   Email: cyril.papamicael@insa-rouen.fr   Email: vgembus@vfp-therapies.com
› Author Affiliations
Further Information

Publication History

Publication Date:
23 September 2016 (online)


Abstract

N-Hydroxysuccinimide esters (NHS-esters) are important and widely used tools in various areas of chemistry including peptide synthesis, bioconjugate chemistry, functionalized materials and polymers. The usual strategy employed to prepare these active esters generally relies on the coupling reaction with a carboxylic acid and N-hydroxysuccinimide in the presence of a coupling agent. However, more recently, many other efficient strategies have emerged in the literature. This short review covers the literature devoted to the preparation of these valuable N-hydroxysuccinimide esters.

1 Introduction

2 N-Hydroxysuccinimide Coupling Reaction with Activated Carboxylic Acids

3 Carboxylic Acid Coupling Reaction with Activated N-Hydroxysuccinimide

4 Alcohol and Aldehyde Coupling Reaction with N-Hydroxysuccinimide under Oxidizing Conditions

5 Carbonylative Cross-Coupling Reaction

6 Conclusion