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Buy Dicyclohexylcarbodiimide (538-75-0) on LEAPChem!

Nov. 2018/1/16 15:22:00 By LEAP Chem


As the name suggests, LEAPChem - Pharmaceutical Chemicals specializes in providing you with those difficult to acquire niche chemicals. We are, however, just as eager and able to provide widely used and recognized chemicals to our valued clients. One such chemical is Dicyclohexylcarbodiimide.

 

Basic Information of Dicyclohexylcarbodiimide

Chemical Name: Dicyclohexylcarbodiimide

Cas No.: 538-75-0

Chemical Formula: C13H22N2

Chemical Structure:
538-75-0.png

 

N,N'-Dicyclohexylcarbodiimide is an organic compound with the chemical formula C13H22N2 whose primary use is to couple amino acids during artificial peptide synthesis. Under standard conditions, it exists in the form of white crystals with a heavy, sweet odor. The low melting point of this material allows it to be melted for easy handling. It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water. The compound is often abbreviated as DCC, DCCD or DCCI.

DCC is a dehydrating agent for the preparation of amides, ketones, nitriles. In these reactions, DCC hydrates to form dicyclohexylurea (DCU), a compound that is nearly insoluble in most organic solvents and insoluble in water. The majority of the DCU is thus readily removed by filtration, although the last traces can be difficult to eliminate from non-polar products. DCC can also be used to invert secondary alcohols.

During protein synthesis (such as Fmoc solid-state synthesizers), the N-terminus is often used as the attachment site on which the amino acid monomers are added. To enhance the electrophilicity of carboxylate group, the negatively charged oxygen must first be "activated" into a better leaving group. DCC is used for this purpose. The negatively charged oxygen will act as a nucleophile, attacking the central carbon in DCC. DCC is temporarily attached to the former carboxylate group forming a highly electrophilic intermediate, making nucleophilic attack by the terminal amino group on the growing peptide more efficient.

 

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References:

https://en.wikipedia.org/wiki/N,N%27-Dicyclohexylcarbodiimide

https://pubchem.ncbi.nlm.nih.gov/compound/dicyclohexylcarbodiimide

https://www.ncbi.nlm.nih.gov/pubmed/23893417

 

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