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N-Hydroxysuccinimide (NHS) is an organic compound with the formula (CH 2 CO) 2 NOH. It is a white solid that is used as a reagent for preparing active esters in peptide synthesis. It can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride. [2]
Disuccinimidyl suberate (DSS) is a six-carbon lysine-reactive non-cleavable cross-linking agent.. It consists of functional groups It is a homobifunctional N-hydroxysuccinimide (NHS) ester formed by carbodiimide-activation of carboxylate molecules, with identical reactive groups at either end. [2]
Succinimides refers to compounds that contain the succinimide group. These compounds have some notable uses. Several succinimides are used as anticonvulsant drugs, including ethosuximide, phensuximide, and methsuximide.
EDC is often used in combination with N-hydroxysuccinimide (NHS) for the immobilisation of large biomolecules. Recent work has also used EDC to assess the structure state of uracil nucleobases in RNA. [2] [3]
The nucleophilic lysine residue is commonly targeted site in protein bioconjugation, typically through amine-reactive N-hydroxysuccinimidyl (NHS) esters. [3] To obtain optimal number of deprotonated lysine residues, the pH of the aqueous solution must be below the pKa of the lysine ammonium group, which is around 10.5, so the typical pH of the reaction is about 8 and 9.
Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a heterobifunctional amine-to-sulfhydryl crosslinker, which contains two reactive groups at opposite ends: N-hydroxysuccinimide-ester and maleimide, reactive with amines and thiols respectively.
BS3 is particularly useful in protein-related applications in that it can react with the primary amines on the side chain of lysine residues and the N-terminus of polypeptide chains. [10] This crosslinker can also be used to stabilize protein-protein interactions for further analysis by immunoprecipitation [ 11 ] or crosslinking mass spectroemtry.
N-Chlorosuccinimide (NCS) is the organic compound with the formula C 2 H 4 (CO) 2 NCl. This white solid is used for chlorinations. [2] It is also used as a mild oxidant. [3] NCS is related to succinimide, but with N-Cl in place of N-H. The N–Cl bond is highly reactive, and NCS functions as a source of "Cl +".