Amino Acids and proteins

M1 lecture

Marie-Véronique CLEMENT
Associate Professor
Yong Loo Lin School of Medicine
NUS Graduate School for Integrative Science and Engineering
Department of Biochemistry
National University of Singapore
8 Medical Drive, MD 7 #03-15
Singapore 117597
Tel: (65) 68747985
Fax: (65) 67791453
  bchmvc@nus.edu.sg
E-mail:  
Did you know?
Amino acids are among the most
common nutritional supplements
taken by athletes
Effect of protein and amino-acid supplementation on athletic performance,
Richard B kreider, phD

Why?
   
 Amino acids are major constituent for brain,
nerve, muscle, blood, skin and internal organs.

your body, minus water, is:

• 75 percent amino acids

• 95 percent of hormones are amino acids

• 100 percent of all protein is amino acids

   
 Beware!!

3 different ways to identify amino acids
   
20 amino acids:

9 Essential amino acids

cannot be manufactured by the body

11 Non-essential amino acids (+ selenocystein)

can be manufactured by the body with proper nutrition.

Alanine Glutamic Acid Lysine Threonine

Arginine Glutamine Methionine Tryptophan

Aspartic Acid Glycine Phenylalanine Tyrosine

Asparagine Histidine Proline Valine

Cysteine-Cystine Isoleucine Serine

Leucine
   
 How to remember the essential amino acid?
cannot be manufactured A helpful mnemonic for
by the body remembering essential
amino acids is

"Private Tim Hall”

(PVT TIM HALL)
P
V
T 
T
I
M
H
Alanine
A
Not required in adult
L
But required in infant diet
L

   
 Where are amino acids coming from?

From the variety of foods in our diet

Meat, milk, cheese, and egg are complete proteins that have all the
essential amino acids.

Other sources of protein include whole grains, rice, corn, beans,

legumes, oatmeal, peas, and peanut butter.

For vegetarians, vegans and/or those who do not eat meat, fish,
eggs, or dairy products, it is important to eat a variety of these
other foods in order to get enough protein.

   
Essential amino acids 
come from breakdown 
of proteins from our food 

Non essential
amino acid
    are metabolized in our body
from glucose
 Glycolysis and the citric acid cycle
provide the precursors needed to synthesize many important
biological molecules including amino acids

   
/Chapter 2  
The general formula of an amino acid:

α-carbon atom

Amino
group Carboxyl group

Side chain
   
Few examples of specific side chains

   
The simplest The most
 amino acid occurent in protein
(9.2%)

The least 
occurent in protein
(1.4%)

Side 
chains

Read chapter 3/
Devlin p 95­98 for 
more details
   
    2 Enantiomers
By convention , if NH3+ is projected to the left, 
the amino acid has an L configuration.

   
 Not an amino acid
It is the simplest of all
common aldoses. It is a
sweet colorless crystalline
solid that is an
intermediate compound in
carbohydrate metabolism

   
 In mammalian proteins only  amino acid  of 
L­configuration are found.

L-Alanine (Ala / A)
L-Asparagine (Asn / N)

L-Arginine (Arg / R)

L-Aspartic acid (Asp / D) L-Threonine (Thr / T)

   
 OR

• Unsubstituted Non Polar
• Heterocyclic Polar charged
• Aromatic Polar uncharged
• Thioether
• hydroxy
• Mercapto
• Carboxiamide
• Monoamino, dicarboxylic
• Diamino, monocarboxylic
   
   
Polar /non Polar: the definition
Polar molecules

Polar molecules are generally able to dissolve in water (hydrophilic) due to the
polar nature of water. Polar molecules have slightly positive and slightly negatively
charged ends.

Examples of household polar molecules include table salt, ammonia and sugar
(glucose).

Non-polar molecules

Most non-polar molecules are water insoluble (hydrophobic) at room temperature.

Examples of household non-polar compounds include fats, oil and petrol.

   
 Polar:  hydrophilic
Non polar: hydrophobic

   
  hyrophobic
 
  Hydrophylic
 
 ?
  Hydrophylic
 
   
Amino acid are in an ionized form at pH 7

   
 Carboxylic acid 
At pH 7: Group
(unprotonated in its 
carboxylate ion form
Amino 
Group
(protonated in its 
amoniun anion form) Hydrogen 
atom

   
Ionization State as a Function of pH. The ionization
state of amino acids is altered by a change in pH. The
zwitterionic form predominates near physiological pH.

   
 Glycine

Histidine

Ionizable 
side chain

    3 acid/base groups
 Leucine
2 acid /base sites

   
 Glutamic 
acid 
3 acid /base 
sites

   
 Amino Acids

Building block of proteins

9 essential
20 Amino Acids:  11 non essential

General formula
 of an Amino Acid
•Unsubstituted
• Heterocyclic
• Aromatic
• Thioether
• hydroxy
All amino acids have a specific side chain • Mercapto
• Carboxiamide
• Monoamino, dicarboxylic
• Diamino, monocarboxylic

All amino acids are in the L­configuration

Amino acid side chain can be 
polar/hydrophilic
  Non polar/hydrophobic 
 Amino acids
view trough photomicrographs (photographs taken through a microscope)

Arginine Valine

Alanine Lysine
   
micro.magnet.fsu.edu/micro/gallery/aminoacid/aminoacid.html
   
 acid base The titration curve of acetic acid
(CH3COOH).

The pKa for the dissociation of acetic

acid to hydrogen and acetate ions is
4.75.

At this pH, half the acid molecules

are dissociated.

Because pH is measured on a
logarithmic scale, the solution
changes from 91 percent CH3COOH
at pH 3.75 to 9 percent CH3COOH at
pH 5.75.

The acid has maximum buffering

capacity in this pH range.

pH = pKa when [A-] = [HA]

   
The four main families of small organic molecules 
in cells

   
 Amino acids are weak acids because of their ionizable groups