N,N'-Disuccinimidyl carbonate
[CAS# 74124-79-1]

Identification

• Classification: Biochemical >> Condensing agent
• Name: N,N'-Disuccinimidyl carbonate
• Synonyms: DSC; Di(succinimido) carbonate; Di-(N,N'-succinimidyl) carbonate
• Molecular Formula: C₉H₈N₂O₇
• Molecular Weight: 256.17
• CAS Registry Number: 74124-79-1
• EC Number: 277-730-3
• SMILES: C1CC(=O)N(C1=O)OC(=O)ON2C(=O)CCC2=O

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 190 °C (decomp.) (Expl.)
• Index of Refraction: 1.597, Calc.^*
• Boiling Point: 383.7±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 185.9±23.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

N,N'-Disuccinimidyl carbonate (DSC) is a widely used chemical compound in biochemistry and molecular biology for crosslinking and modifying proteins, peptides, and other biomolecules. It plays a significant role in covalently binding two molecules together through the formation of an amide bond, providing a versatile tool for studies that require molecular conjugation or immobilization.

DSC was first described in the literature as a useful reagent in protein chemistry in the mid-20th century. Since its discovery, it has been used extensively for crosslinking proteins and other macromolecules in research applications. The molecule itself is an amide derivative of succinimide, containing a reactive carbonate group that allows for the attachment of amine-containing molecules. The reactivity of the carbonate group makes DSC highly effective in bioconjugation, especially in creating stable links between biomolecules such as antibodies, antigens, and synthetic peptides.

The primary application of DSC is in the crosslinking of proteins and peptides for structural studies or for creating immunoconjugates used in diagnostic or therapeutic settings. In drug delivery systems, DSC can be used to attach drugs to targeting agents or delivery vehicles, ensuring a specific interaction with the intended biological target. This application has been crucial in enhancing the precision and efficacy of drug delivery, particularly in targeted cancer therapies, where monoclonal antibodies are linked to chemotherapeutic agents.

In addition to its uses in crosslinking, DSC is utilized in the synthesis of various functionalized materials. It has been employed in the development of biosensors, where the functionalization of surfaces with biomolecules improves the sensitivity and specificity of detection. The ability to modify surfaces with DSC also plays a significant role in the creation of biosurface materials, which are essential in fields such as diagnostics and bioelectronics.

Beyond protein and peptide applications, DSC also finds use in other areas such as biopolymer modification and the creation of hybrid materials. In these areas, DSC can be used to graft functional groups onto polymer chains, enhancing the properties of the materials for specific applications, such as in the development of advanced materials for biotechnology and nanotechnology.

The chemical reactivity of DSC and its ability to form stable amide bonds make it a crucial tool in many areas of chemical and biological research. Despite its utility, DSC is often handled with care due to its highly reactive nature, which requires appropriate safety precautions when used in laboratory settings.

References

1994. Acylation of amino functions of proteins with monomethoxypoly (ethylene glycol)-N-succinimide carbonate. Applied Biochemistry and Biotechnology, 49(1).
DOI: 10.1007/bf02888849

2021. Automated, flow-based chemiluminescence microarray immunoassay for the rapid multiplex detection of IgG antibodies to SARS-CoV-2 in human serum and plasma (CoVRapid CL-MIA). Analytical and Bioanalytical Chemistry, 413(22).
DOI: 10.1007/s00216-021-03315-6

2023. Promoted Comprehensive Properties of Polyisoprene Rubber with Extremely High Fatigue Resistance Enabled by Oligopeptide Aggregates. Chinese Journal of Polymer Science, 41(8).
DOI: 10.1007/s10118-023-2933-3