Peptide bond

Diagram showing the π-bonded amino acids and the point of rotation

A peptide bond is a chemical bond formed between two molecules when the carboxyl group of one molecule reacts with the amino group of the other molecule, releasing a molecule of water (H₂O). This is a dehydration synthesis reaction, and usually occurs between amino acids.

Dehydration synthesis reaction

The resulting C-N bond is called a peptide bond, and the resulting molecule is called an amide. Polypeptides and proteins are chains of amino acids held together by peptide bonds. The backbone of PNA is also held together by peptide bonds.

The C-N bond has a partial double bond character (with the Nitrogen atom attaining a partial positive charge and the oxygen atom a partial negative charge) and the molecule can normally not rotate around this bond. The whole arrangement of the four C,O,N,H atoms as well as the two attached carbons in a peptide bond is planar.

A peptide bond can be broken by amide hydrolysis (the adding of water). The peptide bonds in proteins are metastable, meaning that in the presence of water they will break spontaneously, releasing about 10 kJ/mol of free energy, but this process is extremely slow. In living organisms, the process is facilitated by enzymes. Living organisms also employ enzymes to form peptide bonds; this process requires free energy. The wavelength of absorbance for a peptide bond is 220-280nm.

de:Peptidbindung fr:Liaison peptidique ja:ペプチド結合