N,N′-Disuccinimidyl carbonate (DSC)

Technical Specifications

Product Description & Scientific Applications

N,N′-Disuccinimidyl carbonate — DSC, di(N-succinimidyl) carbonate — is a carbonylating and activating reagent carrying two N-hydroxysuccinimide groups on a central carbonyl. The succinimidyl groups are good leaving groups, allowing DSC to convert carboxylic acids into N-succinimidyl esters and to activate alcohols or amines as N-succinimidyl carbonates or carbamates. DSC is a white to off-white crystalline solid, soluble in acetonitrile, DMF, DMSO and other organic solvents but insoluble in water, and is moisture-sensitive.

Common Scientific Applications

• N-Succinimidyl (NHS) esters from carboxylic acids: DSC converts N-protected amino acids and other carboxylic acids into their N-succinimidyl esters for amide and peptide bond formation.
• Alcohol activation, carbamates and ureas: as an alkoxycarbonylating reagent, DSC activates primary and sterically hindered secondary alcohols as N-succinimidyl carbonates, which react with amines to give structurally diverse carbamates; it is likewise used to prepare ureas, serving as a crystalline phosgene analogue for carbonyl transfer.
• Bioconjugation and surface immobilisation: the N-succinimidyl carbonates and carbamates derived from DSC couple ligands to lysine amines on proteins, and are used to functionalise solid supports, polymer brushes and gold-anchored thiophospholipids for biomolecule attachment.
• Cleavable linkers and amino-compound analysis: DSC is used to prepare the heterobifunctional, cleavable linker SVEC (succinimidyl vinylsulfonylethyl carbonate) for thiol-modified DNA, and as a derivatising reagent for the HPLC determination of amino compounds.

Further Reading

For guidance on selecting between carbodiimides, aminium/uronium salts, phosphonium salts and other reagent classes for amide and peptide bond formation, see NorrChemica's Lab Journal guide: Choosing a Coupling Reagent for Amide and Peptide Bond Formation.

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