PEPTIDE BONDS

In proteins, amino acids are linked by a peptide bond which is formed when the carboxyl (-COOH)
group of one amino acid reacts with the amino (-NH2) group of the next amino acid with the
elimination of a water moiety (dehydration).

While hydrogen bonds are relatively weak, most biological materials including proteins, sugars, fats,
and nucleic acids are composed of molecules in which the constituent atoms are linked together by
covalent bonds. In covalent bonds, two electrons are shared between the bonding orbitals of the
joined atoms. These bonds range in enthalpic energy from about 250 to 400 kJ/mol with the exact
value depending on the atoms involved. For example, carbon-carbon bonds have an average energy
of 348 kJ/mol, while carbon-nitrogen bonds and carbon-oxygen bonds have energies of 293 kJ/mol
and 358 kJ/mol, respectively. Several specially named covalent bonds have achieved this recognition
in the biological sciences because of their biological importance. However, no other covalent bond
has received the attention of that which joins the amino acid monomers that comprise the
polymeric structures known as peptides and proteins. The basis for the extensive study of covalence
in protein structure lies in the fact that proteins are primarily responsible for catalysing the
innumerable array of chemical reactions that maintain life. Thus, we should begin our consideration
of biological molecules with the study of the amino acids and the peptide bond, which is the
specially named bond that links amino acids into covalent polymeric structures. These structures
include small peptide hormones with fewer than 10 amino acids, up to commonly encountered
proteins with an amino acid content ranging from several hundred to more than one thousand. With
the 20 different amino acids having an average molecular weight (M.W.) of 120 Daltons (Da), the
later values correspond to approximate molecular weights of 1200 Da for a 10 amino acid peptide
and 60,000 Da for a 500 amino acid protein. One of the largest proteins discovered is titin, a muscle
cell protein comprised of 27,000 amino acids with a corresponding M.W. of about 3.2! 106 Da