EDC is a water soluble carbodiimide

Carbodiimide

A carbodiimide or a methanediimine is a functional group consisting of the formula RN=C=NR. Carbodiimides hydrolyze to form ureas, which makes them uncommon in nature.-Carbodiimide formation:...

 usually obtained as the hydrochloride

Hydrochloride

In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....

. It is typically employed in the 4.0-6.0 pH

PH

In chemistry, pH is a measure of the acidity or basicity of an aqueous solution. Pure water is said to be neutral, with a pH close to 7.0 at . Solutions with a pH less than 7 are said to be acidic and solutions with a pH greater than 7 are basic or alkaline...

 range. It is generally used as a carboxyl activating agent for the coupling of primary amines to yield amide bonds. Additionally, EDC can also be used to activate phosphate

Phosphate

A phosphate, an inorganic chemical, is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry and biogeochemistry or ecology. Inorganic phosphates are mined to obtain phosphorus for use in...

 groups. Common uses for this carbodiimide include peptide synthesis, protein crosslinking to nucleic acid

Nucleic acid

Nucleic acids are biological molecules essential for life, and include DNA and RNA . Together with proteins, nucleic acids make up the most important macromolecules; each is found in abundance in all living things, where they function in encoding, transmitting and expressing genetic information...

s and preparation of immunoconjugate

Immunoconjugate

Immunoconjugates are antibodies conjugated to a second molecule, usually a toxin, radioisotope or label.These conjugates are used in immunotherapy and to develop monoclonal antibody therapy as a targeted form of chemotherapy when they are often known as antibody-drug conjugates.When the conjugates...

s. EDC is often used in combination with N-hydroxysuccinimide

N-Hydroxysuccinimide

N-Hydroxysuccinimide is a compound with a molecular weight of 115.09 and a melting point of 95 °C.As it is slightly acidic, it is an irritant to skin, eyes and mucous membranes....

 (NHS) or sulfo-NHS to increase coupling efficiency or create a stable amine-reactive product.

EDC also used in organic chemistry to couple a carboxylic acid to alcohol using DMAP

4-Dimethylaminopyridine

4-Dimethylaminopyridine is a derivative of pyridine with the chemical formula 2NC5H4N. This colourless solid is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich...

 as a catalyst.

Preparation

EDC is commercially available. It may be prepared by coupling ethyl isocyanate with N,N-dimethylpropane-1,3-diamine to give a urea

Urea

Urea or carbamide is an organic compound with the chemical formula CO2. The molecule has two —NH2 groups joined by a carbonyl functional group....

, followed by dehydration

Dehydration

In physiology and medicine, dehydration is defined as the excessive loss of body fluid. It is literally the removal of water from an object; however, in physiological terms, it entails a deficiency of fluid within an organism...

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External links

• EDCI coupling - Synthetic protocols from organic-reaction.com