N-Hydroxysuccinimide (NHS)

Introduction

N-Hydroxysuccinimide (NHS, NHSI, or HOSu), a white crystalline solid with a melting point of 99-100 ˚C, was first introduced by Anderson in peptide synthesis. [¹] Since then, NHS has been widely used as activating or protecting reagent in organic and bio-organic synthesis [²] because of its high reactivity, good hydrophilicity, ease of formation of peptide bonds, and commercial availability. Recently, NHS has been exploited for a number of other utilities in synthetic chemistry: it was used as auxiliary for oxidations, activating reagent for selective reductions and coupling reactions of bulky substrates, additive for acceleration of Passerini reactions under aqueous conditions, and efficient ligand for N-arylations. NHS can easily be prepared from equivalent amounts of succinic anhydride and hydroxylamine hydrochloride. [³]

Figure 1 N-Hydroxysuccinimide (NHS)

References

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