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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 .
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]
Common uses for this carbodiimide include peptide synthesis, protein crosslinking to nucleic acids, but also in the preparation of immunoconjugates. 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.
Maleimide-mediated methodologies are among the most used in bioconjugation. [5] [6] Due to fast reactions and high selectivity towards cysteine residues in proteins, a large variety of maleimide heterobifunctional reagents are used for the preparation of targeted therapeutics, assemblies for studying proteins in their biological context, protein-based microarrays, or proteins immobilisation. [7]
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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.
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.
The radical derived by removal of a hydrogen atom from N-hydroxyphthalimide is called N-phthalimido-N-oxyl, acronym being PINO. It is a powerful H-atom abstracting agent. [ 1 ] The bond dissociation energy of NHPI (i.e., PINO–H) is 88–90 kcal/mol (370–380 kJ/mol), depending on the solvent.