1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Chemical properties

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is a white crystalline powder. It is commonly used as an activating reagent in amide synthesis to activate carboxyl groups. It can also activate phosphate groups, cross-link proteins and nucleic acids, and produce immunocouplers.

What are the applications of Application

EDC hydrochloride is a water soluble carboxyl activating carbodiimide reagent, used for amide bond formation.

Biochem/physiol Actions

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(25952-53-8) is a water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines. Additionally, it reacts with phosphate groups. It has been utilized in peptide synthesis, crosslinking proteins to nucleic acids as well as preparation of immunoconjugates.

Mechanism of action

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is transformed into the corresponding urea during coupling reactions. It has the advantage over DCU in that it can be removed from the reaction mixture by extraction or be washed out from solid phase synthesis applications. However, the O-acylisourea can rearrange irreversibly to an N-acyl urea and racemise the α-carbon of the amino acid via the formation of an oxazol-4(5H)-one [azlactone]. N-Acylurea formation and racemisation may be reduced by using intermediate nucleophiles, which convert the O-acylurea to an activated ester containing the nucleophile. The mechanism of amide bond formation applies both to EDC and EDC.HCl.

Synthesis

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride can be used for the synthesis of amides.It is used as a coupling agent in the synthesis of esters from carboxylic acids using dimethylaminopyridine as the catalyst.
Preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(CN104193654A)

Description

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC or EDAC) is a zero-length crosslinking agent 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.

The Uses of 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

EDC hydrochloride is a water-soluble derivative of carbodiimide useful for conjugating haptens to proteins and polypeptides. Used to modify NMDA receptors and as a condensing agent in peptide synthesis.