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1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, EDAC or EDCI) is a water-soluble carbodiimide usually handled as the hydrochloride. [1] It is typically employed in the 4.0-6.0 pH range. It is generally used as a carboxyl activating agent for the coupling of primary amines to yield amide bonds.
The acid 1 will react with the carbodiimide to produce the key intermediate: the O-acylisourea 2, which can be viewed as a carboxylic ester with an activated leaving group. The O-acylisourea will react with amines to give the desired amide 3 and urea 4. The possible reactions of the O-acylisourea 2 produce both desired and undesired products.
N,N′-Dicyclohexylcarbodiimide (DCC or DCCD) [1] is an organic compound with the chemical formula (C 6 H 11 N) 2 C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artificial peptide synthesis.
A common way to synthesize an NHS-activated acid is to mix NHS with the desired carboxylic acid and a small amount of an organic base in an anhydrous solvent. A coupling reagent such as dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) is then added to form a highly reactive activated acid intermediate.
1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide This page was last edited on 7 September 2024, at 08:38 (UTC). Text is available under the Creative Commons ...
Ethyl cyanohydroxyiminoacetate (oxyma) is the oxime of ethyl cyanoacetate and finds use as an additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptide synthesis. It acts as a neutralizing reagent for the basicity or nucleophilicity of the DCC due to its pronounced acidity ( pKa 4.60) and suppresses base catalyzed side ...
In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. [1] The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides.
The Lewis diagram for NCN 2-showing the symmetric carbodiimide form (1) and the asymmetric cyanamide form (2). Inorganic carbodiimides (or cyanamides depending on the NCN 2-form) design a family of compounds containing the carbodiimide (or cyanamide) anion NCN 2-bonded to an inorganic group such as a metal.