Carbodiimide - DCC

DCC (acronym for N,N'-dicyclohexylcarbodiimide) was one of the first carbodiimides developed. It is widely used for amide and ester formation, especially for solid-phase peptide synthesis. DCC has achieved popularity mainly because of its high yielding amide coupling reactions and the fact that it is quite inexpensive.

However, DCC does have some serious drawbacks, and its use is often avoided unless necessary, for several reasons:

1. The byproduct N,N'-dicyclohexylurea is mostly removed by filtration, but trace amounts remain and are often difficult to remove.
2. DCC is incompatible with traditional solid-phase peptide synthesis. The formed N,N'-dicyclohexylurea is mostly insoluble and is difficult to separate from the peptide resin.
3. DCC is a potent allergen, repeated contact with skin increases the probability of sensitization to the compound. Clinical reports of individuals who cannot enter rooms where peptide coupling agents are used have been reported.

For alternative to DCC in coupling see (Coupling Reagents BOP, DCC) at : http://www.biocis.u-psud.fr/spip.php?article332