Amino Acid and Peptide:

Lecture Outline
The amino acids of protein
General properties
Peptide bonds
Classifications
Acid-base properties
Optical Activity
Chirality
Amino Acids
Amino acids are carboxylic acids which
also contain an amino (- NH
2
) group.
Those occuring in proteins are almost
exclusively -amino acids ie the carboxyl
and amino groups are attached to the
same carbon atom (the -carbon)
General structural formula for -
amino acids.
P
a
g
e

6
5
Zwitterionic form of the
-amino acids that
occur at physiological
pH values.
P
a
g
e

6
5
Classification
AA are classified according to the side chain, R:
the most useful way to do this according to their
hydrophobicity, which determines their function
in proteins.
The most hydrophobic are those with large apolar
side chains, the most hydrophilic those with
charged side chains.
The structures of the 20 aas commonly occurring
in proteins are given.
AA are often denoted by abbreviations of three
letters (in most cases the first 3 letters of the
name)
THE PEPTIDES
Compounds of two amino acids linked by a peptide
bond are known as dipeptides
3 aa are called as tripeptides and so on
Oligopeptides contain an unspecified but small
number of aa residues
Polypeptides comprise larger numbers
Natural peptides of 50 or more residues are called
proteins
Condensation of two -amino acids to form a dipeptide.
P
a
g
e

6
8
The peptide bond is shown in red
The aa polymerize through the
elimination of a water molecule
Linear polymers of aa have one -NH
2
and one -
COOH which are not involved in the peptide bond
formation
The aa bearing these are known as the N-terminus
and C-terminus respectively
AA sequences are conventionally written from N-
terminus to C-terminus
Asp-Arg-Val-Tyr-Ile-His-Pro-Leu-Phe
N-terminus
C-terminus
What is CHIRALITY ?
A chiral object is not
superimposible on its
mirror image.Examples
include hands, socks and
keys..
The two forms of a chiral
object are known as
Enantiomers, namely (R)-
and (S)-enantiomers.
Enantiomers are mirror
images of each other.
AA are all optically active.
Optically active molecules are chiral
compounds.
This situation is characteristics of
substances that contain tetrahedral C
atoms that have four different
substituents.
Nonstandard AA
The 20 common aa are not the only aa
that occur in the biological systems.
Nonstandard aa residues are often imp.
Constituents of proteins.
These residues result from the specific
chemical modifications of aa residues in
preexisting proteins.
Roles of these aa includes as
neurotransmitters, metabolic
intermediates and poisons.
Some uncommon amino acid residues
that are components of certain
proteins.