Why is dicyclohexylcarbodiimide DCC used in peptide synthesis?
N,N′-Dicyclohexylcarbodiimide (DCC or DCCD) is an organic compound with the chemical formula (C6H11N)2C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artificial peptide synthesis. The low melting point of this material allows it to be melted for easy handling.
What is DCU soluble in?
Chemical Properties
| Storage | Store at -20°C |
|---|---|
| Synonyms | DCU,NSC 17013 |
| Solubility | insoluble in H2O; insoluble in EtOH; ≥4.53 mg/mL in DMSO with gentle warming |
| Chemical Name | 1,3-dicyclohexylurea |
| SDF | Download SDF |
Is DCC soluble in DCM?
DCC is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.
What is DCC used for?
DCC (dicyclohexyl carbodiimide) is one of the most frequently used coupling agents, especially in organic synthesis applications. It has been used for peptide synthesis since 1955 (Sheehan and Hess, 1955) and continues to be a popular choice for creating peptide bonds (Barany and Merrifield, 1980).
Is DCC an acid or base?
Both DCC and the amine are bases so I don’t think you would need (or want) to add another base.
Is DCC moisture sensitive?
Chemical Properties Moisture Sensitive. Store under Nitrogen. Ambient temperatures. Soluble in methanol, chloroform, dichloromethane, acetonitrile, tetrahydrofuran and dimethylformamide.
Is DCU soluble in water?
The solubility of Dicyclohexylurea in water is less than 1% in water. However in ethanol the solubility is more. It is poorly soluble in water.
Is DCU soluble in acetonitrile?
Do the reaction in acetonitrile as the solvent, when the reaction has finished put the vessel in the fridge or freezer overnight and the DCU will crystallise out. You can then filter. This method is pretty efficient as apart from DCU most compounds I have come across are fairly soluble in acetonitrile.
Is DCC soluble in ethanol?
These days I prefer DIC or HBTU over DCC. I have checked the solubility and the compound is soluble is DCM, Ethyl acetate, diethyl ether, chloroform, methanol and ethanol.
Is DCC water soluble?
The low melting point of this material allows it to be melted for easy handling. DCC is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.
How do I remove DCC urea?
As for the DCC, it is converted into dicyclohexyl urea (DCU) at the end of the reaction if a maximum of two equivalents were used. DCU removal is quite easy. Filtering the reaction mixture through a pad of celite and rinsing with minimal amount of the reaction solvent will get rid of most of it.
Is DCC a base?
The first step is for DCC to function as a base. And so this lone pair of electrons on the nitrogen take this proton, leave these electrons behind on your oxygen.
How do you quench a DCC?
Add cold acetone or dissolve your compound in DCM and put it in a freezer. Adding ether will also do.
How do you quench a reaction?
In a chemical quench setup (i.e., a quench flow), the reaction of interest is initiated by forcing the reactants together into a reaction loop using a rapid mixer, similarly to a stopped-flow instrument.
What is quenching agent?
Quenching agents (QAs) are widely used in order to prevent the additional formation of disinfection by-products (DBPs) during the sample holding time. In addition, DBP levels are usually stabilized by adjusting the pH of water samples.
What is the difference between quenching and annealing?
After quenching, metal tends to become brittle, and that can increase the risk of breakage. Annealing balances the properties of metal alloys to maximize strength and durability for a variety of applications. Annealing removes residual stresses in the metal, improves machinability and makes the metal more formable.