AMINO ACIDS • Introduction

• Classification of amino acids

• Optical activity
• Reactions of amino acids
• Zwitterions
• Formation of peptide bond
 INTRODUCTION
 Amino acids are organic compounds having two functional groups, namely the carboxyl
functional group (-COOH) and the amino functional group (-NH 2)
α-Amino acids Non α-Amino acids
 Carboxyl and amino group are bonded to  carboxyl and amino group bonded to different
the same carbon atom carbon atom

Eg : Eg :
CLASSIFICATION OF AMINO
ACIDS
Neutral Acidic Basic
 Equal number of carboxyl  Has an extra of COOH group  Has an extra of NH2 group
and amino
 EXERCISE
Give the IUPAC name for:

 Glycine –

 Alanine –

 Phenylalanine –

 Valine –

 Lysine –

 Threonine -
 EXERCISE
Select a/ an
1. A : CH3CH2NH2 i. Non amino acid A
B : 2-amino-1,4-butanedioic acid ii. Amino acid which is not
α-
amino acids
C : 3-aminopentanoic acid iii. Acidic α-amino acids
iv. Basic α-amino acids
v. Neutral α-amino acids
D : 2,5-diaminopentanoic acid

E : 2-amino-3-phenylpropanoic acid

F: 4-aminobenzoic acid
1. A : CH3CH2NH2
EXERCISE
B : 2-amino-1,4-butandioic acid
C : 3-aminopentanoic acid
D : 2,5-diaminopentanoic acid
E : 2-amino-3-phenylpropanoic acid
F: 4-aminobenzoic acid

Select a/ an
i. Non amino acid
ii. Amino acid which is not α-amino acids
iii. Acidic α-amino acids
iv. Basic α-amino acids
v. Neutral α-amino acids
 OPTICAL ACTIVITY
 All α-amino acids are optically active except glycine which does not have chiral centre.
 Draw an optical isomers of alanine and serine.
DRAW AN OPTICAL ISOMER OF COMPOUNDS SERINE.
DRAW AN OPTICAL ISOMER OF COMPOUNDS ALANINE.
 ZWITTERIONS
 Definition: molecules with a positive charge on one atom and a negative charge on another atom
in the same molecule.
 Amino acid exists as a dipolar ion when -COOH loses H+, -NH2 gains H+.

 In aqueous solution, an alpha amino acid may exist as either zwitterions, a cation or an anion,or as
an equilibrium mixture of these ions, depending on the pH of the solution
 In a strongly ACIDIC solution, α-amino acid exists predominantly as a CATION
 In a strongly ALKALINE solution, α-amino acid exists predominantly as an ANION
 ISOELECTRIC POINT (pI) = pH at which amino acids exist as the zwitterion (neutral).
 In a strongly ACIDIC solution, α-amino acid exists predominantly as a CATION

ACIDIC
- Cation
- pH < pI
 In a strongly ALKALINE solution, α-amino acid exists predominantly as an ANION

ALKALINE
-
Anion
- pH
> pI
 ACIDIC

- Cation
- pH < pI

 BASIC

- Anion
- pH > pI

 NEUTRAL (ZWITTERION)

- Amphoteric
- pH = pI
 REACTIONS
Carboxylic acids

Amino group
 CHEMICAL REACTION
 Similar to the reaction of primary amines and carboxylic acids.
 Can disturb Amines properties.

1. Reaction with Acids

2. Reaction with acyl chlorides
3. Reaction with nitrous acid
 Can disturb Carboxylic acid properties.

1. Reaction with reactive metals

2. Reaction with Alkalis
3. Esterification
4. Reduction
 CHEMICAL REACTION
 Similar to the reaction of primary amines and carboxylic acids.
 Can disturb Amines properties.

1. Reaction with Acids

2. Reaction with acyl chlorides
3. Reaction with nitrous acid
 Can disturb Carboxylic acid properties.

1. Reaction with reactive metals

2. Reaction with Alkalis
3. Esterification
4. Reduction
CHEMICAL REACTION
CHEMICAL REACTION
FORMATION OF PEPTIDE
BOND/LINKAGE
 Amines and carboxylic acids can undergo condensation reactions, through the loss of water
molecules to form amides
Condensation between two amino acids : dipeptide
Condensation between three amino acids : tripeptide
Condensation of too many amino acids : polypeptide
 The amide linkage between amino acids is called the peptide linkage or peptide bond.