PEPTIDES

By
DR ZARINA ZAKARIA
 PEPTIDES
• Peptide: a polymer of about 2-100 AAs
linked by the peptide(amide) bond. As the
amino group and the carboxyl group link,
water is lost.
• A peptide is written with the N-terminal
end to the left and the C-terminal end to
the right.
• H2N-Tyr-Ala-Cys-Gly-COOH
• Name = Tyrosylalanylcysteinylglycine
• The peptide bond is rigid and planar due
to the resonance contribution shown right.
• Amino acids consists of carboxyl groups,
amino groups, and various R groups can
undergo numerous chemical reactions.
• Polypeptides are linear polymers.
• They are composed of amino acids that
linked together by peptide bonds.
• Peptides bonds are amide linkages.
• The linkages formed when the unshared
electron pair of the -amino nitrogen atom
of one amino acid attacks the -carboxyl
carbon.
• The linked amino acids are referred to as amino
acid residues.
• The amino acid residue with the free amino
group is called the N-terminal residue and
written to the left of polypeptide.
• H2N-Tyr-Ala-Cys-Gly-COOH
Name = Tyrosylalanylcysteinylglycine

• The amino acid residue with free carboxyl group

is called the C-terminal residue and written to
the right of a polypeptide.
• The C-terminal residues can be identified
by a group of enzymes called the
carboxypeptidases.
• The N-terminal residues is determined
using Sanger’s method where the
polypeptide chain is reacted with 1-fluoro-
2,4-dinitrobenzene.
DEFRAGMENTATION OF POLYPEPTIDE
- The cleavage or broken up of polypeptides
done by using several reagents, mostly
the enzymes.
- The pancreatic enzyme, trypsin is most
commonly used.
- Trypsin cleaves peptide bonds on the
carboxyl side of either lysine or arginine
residues.
- Chymotrypsin, another pancreatic
enzyme, breaks peptide bonds on the
carboxyl side of phenylalanine, tyrosine or
trptophan.
• Cyanogen bromide is a reagent
specifically cleaves peptide bonds on the
carboxyl side of methionine residues.
• 1-fluoro-2,4-dinitrobenzene (DNFB) has
been used to determine the N-terminal
amino acids.
• The N-terminal is identified as the
dinitrophenyl (DNP) is attached to the
terminal after reaction.
• Carboxypeptidases hydrolizes peptides
one residue at a time from the C-terminal
end.