Ethylene Glycol bis(succinimidyl succinate)
Properties
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Information about Ethylene Glycol bis(succinimidyl succinate) / CAS 70539-42-3
Ethylene Glycol Bis(succinimidylsuccinate) (EGS) is a crosslinking agent commonly used in biological research to study peptides and proteins. The molecule features two N-hydroxysuccinimide (NHS) esters at each end, which react with primary amine groups on polypeptide chains or the side-chain of lysine amino acids. A 12-atom spacer arm separates these NHS esters.
EGS is water-insoluble but dissolves in DMF (Dimethylformamide) or DMSO (Dimethyl Sulfoxide), and due to its solubility, it is membrane-permeable. This makes it suitable for intracellular crosslinking studies. The crosslinks formed by EGS can be broken by reacting with hydroxylamine at a pH of 8.5, allowing for controlled disassembly of protein interactions.
A related compound, Sulfo EGS (Ethylene Glycol Bis(sulfosuccinimidylsuccinate)), has a sulfonated group that makes it water-soluble, but it is impermeable to cellular membranes. As a result, Sulfo EGS is used primarily for labeling the surface of cell membranes, enabling studies of extracellular protein interactions.
References:
- Abdella, R.M., Smith, P.K. and Royer, G.P. (1979) Biochem. Biophys. Res. Commun. 87, 734-742.
- Conn, P.M., et al. (1982) Nature 296, 653-655.
- Running, J.A. and Urdea, M.S. (1990) Biotechniques 8, 276-278.