ANALYSIS OF BIOLOGICAL SYSTEM

Amino Acids and Use of Amino Acids

 Outline
• Introduction
• Analysis of Biological System
• Outline of Biochemistry Section
• Amino Acids and Proteins
• Amino Acids
• Use of Amino Acids
Outline of Biochemistry Section
Contents-Cell construction
• Protein and amino acids
• Carbohydrates
• Lipids, fats and steroids
• Nucleic acids, RNA and DNA

Requirements:
Understand the basic definitions, characteristics
and functions of these biochemicals.
 Amino Acids and Proteins

Proteins are the most abundant molecules

in living cells, constituting 40% - 70% of
their dry weight. Proteins are built from
monomers.

Amino acid is any molecule that contains

both
functional groups.
 Amino Acids
H
α
H2N C COOH

Where "R" represents a side chain specific to each amino acid.

Amino acids are usually classified by properties of the side chain into
four groups.
acidic, basic, hydrophilic (polar), and hydrophobic (nonpolar).
α-amino acid are amino acid in which the amino and carboxylate
functionalities are attached to the same carbon, the so-called α–
carbon.
They are the building blocks of proteins.
 Amino Acids
Zwitterion is an amino acid having positively and negatively
charged groups, a dipolar molecule.

H H H
-H+ -H+
H3N+ C COOH H3N+ C COO- H2N C COO-
+H+ +H+
R R R
Zwitterion
 Amino Acids
Isoelectric point (IEP) is the pH value at which amino acids
have .
IEP varies depending on the R group of amino acids.
At IEP, an amino acid does not migrate under the influence of
an electric field.

pH effect on the charge of amino acids

We can arbitrarily control the pH of an aqueous solution
containing amino acids by adding base or acid. The
equilibrium reactions for the simple amino acid (HA) are
HAH+ = H++AH (1)
HA = H++A- (2)
 Amino Acids

pH effect on the charge of amino acids

The proton dissociation constants are K1, K2

[ HA][ H ] + [ A− ][ H + ]
K1 = (3) K2 = (4)
[ HAH + ] [ HA]
Taking the logs of equations 3 and 4, yields,

pH = pK1 + log
[ HA] [ A− ]
(5) pH = pK 2 + log (6)
[ HAH + ] [ HA]
[ ] represents concentration in dilute solution.
where pH=-log(H+), pK1=-log(K1), and pK2=-log(K2).
Standard amino acids: there are 20 standard amino acids
that are commonly found in proteins.
 Amino Acids
Essential amino acids: An essential amino acid for an organism
is an amino acid that cannot be synthesized by the organism
from other available resources, and therefore must be supplied
as part of its diet.
Most of the plants and microorganism cells are able to use
inorganic compounds to make amino acids necessary for the
normal growth.

Eight amino acids are generally regarded as essential for humans:

tryptophan, lysine, methionine, phenylalanine, threonine, valine,
leucine, isoleucine.
Two others, histidine and arginine are essential only in children.

A good memonic device for remembering these is "Private Tim

Hall", abbreviated as:
PVT TIM HALL:
Phenylalanine, Valine, Tryptophan
Threonine, Isoleucine, Methionine
Histidine, Arginine, Lysine, Leucine
 Non and Essential Amino Acids
Essential amino acids Non-Essential amino acids
• Arginine ◼ Alanine (from pyruvic acid)
• Histidine ◼ Asparagine (from aspartic acid)
• Isoleucine ◼ Aspartic Acid (from oxaloacetic acid)
• Leucine ◼ Cysteine
• Lysine (aspartate)
◼ Glutamic Acid (from oxoglutaric acid)
• Methionine
◼ Glutamine (from glutamic acid)
• Phenylalanine
◼ Glycine (from serine and threonine)
• Threonine
◼ Proline (from glutamic acid)
• Tryptophan
• Valine ◼ Serine (from glucose)

Private (PVT) Tim Hall ◼ Tyrosine (from phenylalanine)

11
limiting amino acid content: O

the essential amino acid found in the smallest H2N CH C OH

quantity in the foodstuff. CH2
Protein source Limiting amino acid
CH2
Wheat lysine
CH2
Rice lysine and threonine
Maize lysine and tryptophan CH2

Pulses Methionine NH2

Beef methionine and cysteine Lysine (Lys, K)

Whey none
Milk none

H2N CH C OH

CH2

SH
Cysteine (Cys, C)
 Pulses
• The dry, edible seeds of plants in the
legume family, pulses are a category of
superfoods that includes chickpeas, lentils,
dry peas and beans.
 O NH2 O
H
N

Use of Amino Acids O

O
OH

H
N
• Aspartame (aspartyl-phenylalanine-1-methyl ester)
is an artificial sweetener.
HO
NH2
• 5-HTP (5-hydroxytryptophan)
has been used to treat neurological problems associated with PKU
(phenylketonuria), as well as depression. O OH
O

• L-DOPA (L-dihydroxyphenylalanine) OH

is a drug used to treat Parkinsonism. N

HO OH

• Monosodium glutamate is a food additive to enhance flavor.

O O

HO O- Na+

NH2
 Aspartame
(aspartyl-phenylalanine-1-methyl ester)
• is an artificial sweetener.
P henylalanine O
HO
H2N CH C OH
O
CH2
O Alanine O

H2N HN H2 N CH C OH

O CH3
O
O

H2 N CH C OH

CH2

C O

OH
aspartic acid ( Asp, D)
 Synthesis of Aspartame (Ester)
O O

H2N CH C OH + CH3OH H2N CH C OCH3 + H2O

CH2 CH2

Phenylalanin-1-methyl ester
O O O H O

H2N CH C OH + H2N CH C OCH3 H2N CH C N C C OCH3

CH2 CH2 CH2 H CH2

C O C O

OH OH
aspartic acid ( Asp, D)
 Aspartame
• Discovered in 1965
• 200 times sweeter than
sucrose
• Approved in over 130
countries
• ADI: 40 (JECFA); 50 (FDA)

Consumption studies: Australia, Brazil, Canada, Denmark, France,

Germany, Italy, Korea, Netherlands, New Zealand, Portugal, Spain, Sweden,
UK, US.
Average users: <1-10% acceptable daily intake (ADI); Highest users: 45%
ADI

No report of even highest user exceeding ADI

 Number of Servings/Day to Reach
Acceptable Daily Intake (ADI)

Food/Beverage Adult 70 kg Child, 23 kg

Carbonated soft drink (12 oz.) 16-20 5-6
Powdered soft drink (8 oz.) 26-33 9-11
Gelatin (4 oz.) 34-42 11-14
Tabletop sweetener (packet) 80-100 26-32
Aspartame metabolism
Intestinal Lumen Mucosa Cell Portal Blood

Aspartame Aspartame

Esterases Esterases

Methanol
Aspartame
(10%) Methanol Aspartame
Methanol
+ does not
Asp/Phe Asp/Phe enter
Peptidases
blood
Peptidases

Aspartate (40%) Aspartate Aspartate

+
Phenylalanine (50%)
+
Phenylalanine
Phenylalanine

Dipeptide Transport
System
 Aspartame controversies
• Is aspartame linked to effects on behavior
or the nervous system?
– Many animal studies:
• Healthy, genetically predisposed, induced disorders
– Many human studies
• Normal children, hyperactive children, children with
PKU, aggressive school boys, sugar-sensitive
children
• Healthy adults, airplane pilots, adults with Parkinson’s
disease, adults with depression
• No effect on learning, cognitive
performance, behavior, seizures, or any
other neurological parameter
 Does aspartame cause cancer?
• 16 chronic animal studies: multiple species
– 14 found no evidence of carcinogenic or promoting
effects of aspartame
– Only studies reporting positive results by Soffritti et al.
• Detailed review of protocol and data of Soffritti by:
– EFSA, 2006; Agence Franciase de Securite Santarie des
Aliments (2006); US National Toxicology Program; FDA,
Health Canada; Expert panel (Crit Rev Toxicology, 2007)
• All agreed that:
– “there is no credible evidence that
aspartame is carcinogenic”
– “no need to further review the safety of aspartame”
– “no need to revise previously established ADI”
 Is aspartame safe for children?
• Metabolism of aspartame
– 1 yr infants and older children;
– No difference between children and adult
• Effect on behavior assessed
– No effect even with habitual use
• Effect on childhood cancers
– No association
Aspartame is safe for children (>1 year) at
levels consumed
 5-hydroxytryptophan (5-HTP)

• has been used to treat neurological problems

associated with phenylketonuria (PKU), as well
as depression.
HO
O Typtophan
O
H
N
H2 N H2 N CH C OH

CH2
HO
NH2

HN OH
OH
HN
O
L-DOPA (L-dihydroxyphenylalanine)

is a drug used to treat Parkinsonism

O O

H2 N CH C OH
OH
CH2
N
HO OH

P henylalanine
 Monosodium glutamate (MSG)

• is a food additive to enhance flavor

O O O
Glutamic acid
H2N CH C OH
- +
HO O Na
CH2
NH2
CH2

C O

OH
 Amino Acid (AA)-Protein
: basic unit

: amino acid chain, containing 2 or more AA.

: containing less than 50 AA.

: > 50 AA.

Peptides (from the Greek πεπτος, "digestible"), are formed through

condensation of amino acids through peptide bonds.
Peptide bond: a chemical bond formed between two AA
- the of one amino acid reacts with

- the of the other amino acid,

- releasing a molecule of .
This is a condensation (also called dehydration synthesis)
reaction.
 References
1. Engr.usask.ca, Year NA, Analysis of Biological System.
www.engr.usask.ca/.../lecture%206/lecture%20notes-biochemis..., Accessed 2
March 2017.
2. Chase, H. The contribution of chemical engineering to biotechnology,
https://www.repository.cam.ac.uk/bitstream/.../HAC60th.ppt, Access 13 July
2018.
3. Chemdraw
4. Magnuson, Bernadene, year NA., Safety Evaluation and Safety of Sweeteners,
www.ilsi-india.org/.../Safety%20Evaluation%20a, Accessed 2 May 2014.
5. Dave, 2016. Protein Structure, http://youtube.com/watch?v=EweuU2fEgjw.
Accessed 14 March 2021.
6. Dave. Amino Acid. 2016. http://youtube.com/watch?v=J6R8zDAl_vw&t=21s.
Accessed 14 March 2021.
7. pulses.org. Year NA. What are Pulses? https://pulses.org/nap/what-are-pulses/.
Accessed 30 March 2021