EDC-HCl (N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride), Pierce™
Supplier: LIFE TECHNOLOGIES MS
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Warning
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Synonyms:
EDAC hydrochloride
, EDAC HCl
, EDC HCl
, EDC
, 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
, WSC HCl
, 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
, N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide monohydrochloride
, EDC hydrochloride
, N'-(Ethylcarbonimidoyl)-N,N-dimethylpropane-1,3-diamine monohydrochloride
Thermo Scientific Pierce EDC is a carboxyl- and amine-reactive zero-length crosslinker. EDC reacts with a carboxyl group first and forms an amine-reactive O-acylisourea intermediate that quickly reacts with an amino group to form an amide bond with release of an isourea by-product. The intermediate is unstable in aqueous solutions and so two-step conjugation procedures rely on N-hydroxysuccinimide (NHS) for stabilization. Failure to react with an amine will result in hydrolysis of the intermediate, regeneration of the carboxyl, and release of an N-substituted urea. A side reaction is the formation of an N-acylurea, which is usually restricted to carboxyls located in hydrophobic regions of proteins.
- Reactive group: carbodiimide
- Reaction target: activates carboxyl groups to conjugate to amino groups (primary amines)
- Several conjugation strategies—react EDC alone with target groups or include NHS or Sulfo-NHS to increase reaction efficiency or to stabilize active intermediate for later reaction to amines
- Neutral linkage—forms neutral amide bonds between carboxyls and amines
- Water-soluble reagent—add directly to reactions in aqueous, physiological buffers
- Soluble reaction byproducts—easily removed by washing with water or dilute acid
- High-purity, crystalline reagent—use to create high-quality, activated derivatives
1-Ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDC or EDAC) is a zero-length crosslinking agent used to couple carboxyl groups to primary amines. This crosslinker has been used in diverse applications such as forming amide bonds in peptide synthesis, attaching haptens to carrier proteins to form immunogens, labeling nucleic acids through 5' phosphate groups and creating amine-reactive NHS-esters of biomolecules. EDC reacts with a carboxyl to form an amine-reactive O-acylisourea intermediate. If this intermediate does not encounter an amine, it will hydrolyze and regenerate the carboxyl group. In the presence of N-hydroxysulfosuccinimide (Sulfo-NHS), EDC can be used to convert carboxyl groups to amine-reactive Sulfo-NHS esters. This is accomplished by mixing the EDC with a carboxyl containing molecule and adding Sulfo-NHS.
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Formula:
C₈H₁₇N₃·HCl MW: 191.7 g/mol Melting Pt: ∼ 113 °C Storage Temperature: Refrigerator |
MDL Number:
MFCD00012503 CAS Number: 25952-53-8 UN: 2811 ADR: 6.1,III |
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Specification Test Results
| Product Line | Pierce™ |
| Labeling Method | Chemical Labeling |
| Crosslinker Type | Heterobifunctional |
| Reactive Moiety | Carbodiimide |
| Spacer | Short |
| Form | Powder |
| Quantity | 10 mg/5 g/25 g |
| Type | Crosslinker |
| Solubility | Water |
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