Chapter 3: Amino Acids and Peptides

 Amino Acids are 3D

o Only 20 amino acids found in proteins
o General structure: amino group+ carboxyl group+ side chain
group
 Structures and Properties of Amino Acids
o R groups classified by 2 important criteria: polar/nonpolar
nature of the side chain and presence of an acidic/basic group in
the side chain
 Amino Acids Can Act as Both Acids and Bases
o Free amino acids: carboxyl and amino group are charged at
neutral pH
 Carboxylate portion: - charge; amino portion: +
o Amino acids w/o charged groups on their side chains exist in
neutral solns as zwitterions w/ no net charge
 Zwitterion: = + and – charges; electrically neutral in soln
o Titration of Amino Acids
 Amino acid is titrated titration curve shows rxn of each
functional group w/ H+
 Titratable groups of amino acids have pKa values
 pKa values of α-carboxyl groups are low (~2)
 pKa values of amino acids are high (9-10.5)
 pKa of R group depends on chem nature
o can have diff charges at a given pH bc they all
have diff pKa values
  electrophoresis: common method for separating
molecules in an electric field
 determines important properties of proteins and
nucleic acids
o Amino Acid Isoelectric Point
 Isoelectric pH (pI): pH at which a molecule has no net
charge
 @ pI, molecule won’t migrate in an electric field
use in separation methods
𝑝𝐾𝑎1+𝑝𝐾𝑎2
 𝑝𝐼 =
2

 acidic and basic amino acids

o pKa1: R group that has dissociated at its pI
 if there’s 2: choose higher pKa
o pKa2: group that hasn't dissociated at pI
 if there’s 2: choose lower pKa
 The Peptide Bond
o Individual amino acids can be linked by covalent bonds
 Water is eliminated in the process and the linked amino
acid residues remain after water is eliminated
o Peptides: compounds formed by linking small #s of amino acids
 Polypeptide chains
o Peptide bond has partial double bond character peptide group
is planar
 Strong bc resonance stabilization
o Free rotation around the bonds bw the α-C of an amino acid
residue but no sig. rotation around peptide bond
 Small Peptides with Physiological Activity

2
 o Hormones
 Ex: steroids
o Some peptide hormones have cyclic structures
 ----S----S---- bond responsible for the cyclic structure in
some hormones