N-Hydroxysuccinimide

1-hydroxy- 2 ,5- pyrrolidinedione

Colorless and odorless crystalline solid

Fixed

99-101 ° C

Readily soluble in water

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N-hydroxysuccinimide ( NHS, usually abbreviated to structural formulas as HOSu, IUPAC 1-hydroxy- 2 ,5- pyrrolidinedione ), the N- hydroxy derivative of succinimide. The substance is used in organic synthesis, especially for the production of so-called NHS ester.

Properties

N- hydroxysuccinimide is a colorless and odorless crystalline solid. It is slightly soluble in water and shows it as a weak acid reaction. NHS is a weak oxidizing agent.

Use

In chemical and biochemical syntheses of N-hydroxysuccinimide is a versatile and frequently used connection.

By reaction with a carboxylic acid and an activating reagent, such as dicyclohexylcarbodiimide ( DCC) or 1-ethyl- 3-(3 -dimethylaminopropyl) carbodiimide (EDC), are thus prepared NHS ester. NHS esters are " activated carboxylic acids " and react readily with amino functions - for example, peptides or proteins - that are much more nucleophilic than alcohols.

NHS esters are relatively stable to hydrolysis.

Similar reagents for activation of carboxylic acids are 1-hydroxybenzotriazole ( HOBT ), 1- hydroxy-7- azabenzotriazole ( HOAT ), and pentafluorophenol.

The oxidizing properties of the NHS can be used for ruthenium - catalyzed conversion of terminal alkynes to carboxylic acid derivatives.

The use of NHS for the preparation of active esters was first described in 1963 by George W. Anderson, Joan E. Zimmerman and Francis M. Callahan.

Toxicology

N- hydroxysuccinimide in an animal model mouse and rat neither carcinogenic nor teratogenic. In the baker's yeast Saccharomyces cerevisiae, it triggers mitotic gene mutations.