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N-Hydroxysuccinimide is used for improved amidations in the carbodiimide method. It is also used to activate a carboxyl group and reacts with amine to form amide. It is involved in the preparation of N-hydroxymaleimide-styrene copolymer. Further, it finds use in analytical chemistry. As an additive, it is used in the carbodiimide method for improved amidations and peptide couplings.
Reagent for the preparation of active N-hydroxysuccinimide esters for peptide coupling with minimum racemization: J. Am. Chem. Soc., 86, 1839 (1964), or as an additive in the DCC method (see N,N'-Dicyclohexylcarbodiimide, A10973 ) to suppress racemization: J. Am. Chem. Soc., 89, 7151 (1967). For peptide reagents, see Appendix 6.
For a study of the aminolysis of N-hydroxysuccinimide esters, see: J. Org. Chem., 53, 3583 (1988).
Park, C.; Vo, C. L. N.; Kang, T.; Oh, E.; Lee, B. J. New method and characterization of self-assembled gelatin-oleic nanoparticles using a desolvation method via carbodiimide/N-hydroxysuccinimide (EDC/NHS) reaction. Eur. J. Pharm. Biopharm. 2015, 89, 365-373.
Peng, Z.; McGee, W. M.; Bu, J.; Barefoot, N. Z.; McLuckey, S. A. Gas phase reactivity of carboxylates with N-hydroxysuccinimide esters. J. Am. Soc. Mass. Spectrom. 2015, 26 (1), 174-180.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant