carbamoyl

Carbamoyl refers to a functional group in organic chemistry characterized by a carbonyl group (C=O) attached to an amide nitrogen, typically represented as -CONH2. In simple terms, it is the amide-derived moiety of carbamic acid. The unsubstituted form is -CONH2, but the nitrogen can also bear substituents, giving -CONR'R'' and related derivatives. The term is commonly used to describe both the specific -CONH2 group and the broader class of N-substituted carbamoyl groups found in various compounds.

In biochemistry and metabolism, the carbamoyl group features prominently in several essential pathways. A key example is carbamoyl phosphate, an important donor of the carbamoyl group in the urea cycle and in pyrimidine biosynthesis. Carbamoyl phosphate is formed by carbamoyl phosphate synthetase from ammonium, bicarbonate, and ATP, and it serves as a carbonyl-nitrogen source for downstream enzymatic reactions that build or dispose of nitrogenous compounds.

In synthetic chemistry, carbamoyl derivatives are widespread. The carbamoyl group can be introduced into molecules via reagents such as carbamoyl chlorides, isocyanates, or related carbonylating agents. The resulting compounds include ureas and related amide-containing materials, which are important in pharmaceuticals, agrochemicals, and material science. The term also appears in discussions of N-substituted carbamoyl groups, where the nitrogen is bonded to one or more carbon substituents, forming a variety of carbamoyl amide structures.

See also: urea, carbamates, carbamoyl phosphate, pyrimidine biosynthesis, urea cycle.