CHAPTER 19: AMINO ACIDS

Amino Acids

Organic compound that contains both an amino group, -NH2 and a carboxyl group, -COOH.
H
H3C

COOH

NH2
amino acid

-amino acid: an amino acid in which the carboxyl and amino groups bonded to the same carbon
atom.

There are about twenty naturally occurring amino acids.

Structure of 20 standard Amino Acids
Name

Structure

Glycine (Gly)

Name

Structure

Isoleucine (Ile)

CH3 H

COOH

H3CH 2C

CH C

NH2

Alanine (Ala)

NH2

H
H3C

COOH

Phenylalanine
(Phe)

CH 2 CH COOH
NH2

NH2

Valine (Val)

NH 2
H2C HC COOH

CH3 H
H3C

CH C

COOH

Tryptophan (Trp)

NH2

Leucine (Leu)

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COOH

N
H

Proline (Pro)

H
H3C CH CH 2 C
CH3

COOH

HO

CH 2 C

COOH

H
HS

CH 2 C

COOH

OH H

Threonine (Thr)

H3C

NH2

Cysteine(Cys)

Aspartic acid
(Asp)

CH 2 CH 2 C

HOOC

COOH

Glutamic acid
(Glu)

CH 2 CH COOH
NH2

HO

Asparagine
(Asn)

COOH

NH2

CH 2 C

COOH

H
HOOC CH 2 CH 2 C

NH2

Tyrosine (Tyr)

NH2

H
H3C S

NH2

Methionine
(Met)

COOH

NH2

Serine (Ser)

H
N

COOH

NH2

H
Lysine(Lys)

H2N CH 2CH 2 CH 2 CH 2 C

COOH

NH2

H2N C

CH 2 C

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NH2

NH2
COOH

Arginine (Arg)

HN

C NH(CH 2)3 C
NH2

COOH

H2N C CH 2CH 2 C

Glutamine
(Gln)

H2N

COOH

H2C

Histidine (His)

NH2

CH COOH
NH

Using IUPAC nomenclature, the carboxyl group, -COOH is highest priority

and labeled as carbon number one

IUPAC Nomenclature of Amino Acids

1.

2.

3.

H
H

COOH

H3C

NH2

5.

NH2

COOH

H2N

COOH

6.

OH H

CH 2 C
NH2

NH2

4.

H3C

HO

COOH

CH 2 CH 2 CH 2 C
NH2

H
COOH

HOOC CH 2 CH 2 C

COOH

NH2

Zwitterion

Zwitterion is a molecule with an overall charge of zero which has a positively charged group at one part and a
negatively charged at another

Amino acids can undergo an internal acid-base reaction, in which a proton is transferred from the carboxyl (-COOH) to the
amino group (-NH2) to form dipolar ion called zwitterion.
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Example :

CH 2CH 2CH 3
H

as acid loss proton

CH 2CH 2CH 3

COOH

C
NH 3

NH2
neutral

as base accept proton

dipolar ion (zwitterion)

In Acidic

In an acid solution, a zwitterions accepts a proton to yield a cation

Amino acids as base (amino group) accept a proton

Example :

CH 2CH 2CH 3
C

COOH

NH 3

Predominates act as base

In Basic

In an basic solution, a zwitterions loss a proton to form an anion

Amino acids as acid (carboxyl group) loss a proton

Example :

CH 2CH 2CH 3
C

COO

NH2

In pI

an amino acid are equal

In general, zwitterion is electrically neutral and exists at specific pH. Each has its specific
pI

Isoelectric points (pI) is the pH at which the number of positive and negative charges on

Isoelectric Point (pI)

COO

A zwitterions is an amphoteric in nature

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Predominates act as acid

Amino acids as amphoteric.

Amino group, -NH2 accepts a proton. Carboxyl group, COOH loss a proton

Example :

CH 2CH 2CH 3
H

C
NH 3

COO
+

Predominates act as amphoteric

Exercises :

1. Isoelectric point of glysine, 2-aminoethanoic acid 5.97. Predict the structure of glysine at :
a)
in acidic solution

b)

in isoelectric point

c) in basic solution

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2.

The pI value of serine 2-amino-3-hydroxypropanoic acid is 5.7. Draw the predominant structural formula of serine
a) In solid state

b) In an aqueous solution at :
i)
pH 1
ii)
pH 14
iii)
pH 5.7

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