1

I. STRUCTURE AND PROPERTIES OF AMINO ACIDS

A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
3
 WHAT ARE AMINO ACIDS?
 building blocks of proteins
 difunctional: contain a basic amino
group and an acidic carboxylic
group
H
O
H N C C OH
H R
 WHAT ARE AMINO ACIDS?
 Amino acids can join together into
long chains by forming amide bonds
between the – NH2 of one amino acid
and the – COOH of another.

H H
O O
H N C C OH H N C C OH
H R H R
HOH
WHAT ARE AMINO ACIDS?
 amino acids joined
together by an amide bond
H H
O O
H N C C N C C OH
H R H R
 WHAT ARE AMINO ACIDS?
 They are the fundamental building
blocks from which the 150,000 or so
different proteins in our bodies are
made.
WHAT ARE AMINO ACIDS?
PROPERTIES OF AMINO ACIDS
H
O
–
H N C C OH
H R

 At a physiological pH of 7.3, a carboxyl group is

deprotonated and exists as the carboxylate
anion…
PROPERTIES OF AMINO ACIDS
H
H O
+ –
H N C C O
H R
ZWITTERION
…while an amino group is protonated and exists as
the .
PROPERTIES OF AMINO ACIDS
 Zwitterions are internal salts, therefore have
many of the physical properties associated
with salts.

 large dipole moments

 relatively soluble in water

 insoluble in hydrocarbons
 crystalline with relatively high melting points
PROPERTIES OF AMINO ACIDS
 Amino acids are amphiprotic; they can react
either as acids or as bases, depending on
circumstances.

H H
O H H O
+ H3O+ +
H N C C O– H N C C OH
H R H R

+ H2O
PROPERTIES OF AMINO ACIDS
 Amino acids are amphiprotic; they can react
either as acids or as bases, depending on
circumstances.

H H H
O O
+ – OH –
H N C C O H N C C O
H R H R

+ H2O
STRUCTURES OF AMINO ACIDS
STRUCTURES OF AMINO ACIDS
H
O
H N C C OH
H R
alpha-carbon

With four different groups

The R-group is often
connected to the tetrahedral
referred to as the
α-carbon atom, α-amino
side chain
acids are chiral **.
STRUCTURES OF AMINO ACIDS

C
STRUCTURES OF AMINO ACIDS
CLASSIFICATION OF AMINO ACIDS
Amino Acids are categorized as:

 ESSENTIAL vs. NON-ESSENTIAL

 based on their R-groups

ESSENTIAL vs. NON-ESSENTIAL
AMINO ACIDS
CLASSIFICATION OF AMINO ACIDS
 Based on R-group

a. ALKYL = with alkyl side chain (or R-group)

20 STANDARD
b. SULFUR-CONTAINING
c. ALCOHOLS = with –OH
amino acids
d. ACIDS = with acidic functional group (e.g. –COOH)

e. BASESfound infunctional
= with basic nearly group (e.g. –
NH )2
all proteins.
f. AROMATIC = with phenyl group
g. AMIDES = with amide group
21
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
R = alkyl group
 GLYCINE

Glycine is the only amino acid that is not chiral

ALANINE
VALINE
LEUCINE
ISOLEUCINE
PROLINE
R = alkyl group

30
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
 R = OH containing
O O
H2N CH C OH H
N
2 C
HCO
H
CH2 C
HO
H
OH C
H
3

32
 SERINE
O
H2N CH C OH
CH2
c

OH

Serine
Ser, S Essential or not:
Molecular formula: C3H7NO3
Molecular weight: 105.9
boiling point: 394.8°C
 THREONINE
O
H
N
2 C
HCO
H
C
HO
H
c

C
H
3
Threonine
Thr, T
Essential or not: essential
Molecular formula: C4H9NO3 Molecular
weight: 119.12
boiling point: 394.8°C
 R = OH containing
O O
H2N CH C OH H
N
2 C
HCO
H
CH2 C
HO
H
OH C
H
3

35
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
 R = S containing
O O
H
N
C
2H
CO
H
H2N CH C OH
C
H
2
CH2
C
H
2
SH S
C
H
3
37
 CYSTEINE
O
H2N CH C OH
CH2
SH

Cysteine
Cys, C

38
 CYSTEINE
This paired unit is now called cystine (note the
difference in spelling). Cystine can easily enter the cell
where it breaks down back into two cysteine molecules
and participates in the formation of glutathione.

39
 METHIONINE
O
H
N
C
2H
CO
H
C
H
2

C
H
2

S
C
H
3
Methionine
Met, M
40
METHIONINE

Methionine cannot be produced

by the body. It is needed for the
formation of cartilages and also for
many other essential functions of
the cells. It is beneficial for
preventing hair loss and to make
your nails stronger. Methionine is
found in high amounts in fish,
meat and dairy products. 41
 R = S containing
O O
H
N
C
2H
CO
H
H2N CH C OH C
H
2

CH2 C
H
2

S
SH
C
H
3

42
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
44
 R = amide
O
O
H2N CH C OH
H2N CH C OH
CH2
CH2
CH2
C O
NH2 C O
NH2

45
 GLUTAMINE
O
H2N CH C OH
CH2
CH2
C O
NH2

Glutamine
Glu, Q

46
 GLUTAMINE
Glutamine was first discovered by Schulze in 1883,
who managed to isolate it from the beet juice.

Later on, it turned out that glutamine

can also be found in abundance in a
wheat gliadin. Finally, in 1935, the
synthesis of glutamine from
ammonium and glutamate was
explained and described by Krebs, who
used the guinea pig and the rat kidney
in his research.

47
GLUTAMINE

48
49
 GLUTAMINE
O
H2N CH C OH Chemical formula C5H10N2O3

CH2
−1
Molar mass 146.15 g·mol
CH2
C O Melting point around 185°C

NH2
Boiling point 445.6 °C
Glutamine
Glu, Q

50
 R = amide
Louis-Nicolas Vauquelin (1763-1829)

Pierre Jean Robiquet (1780-1840)

51
 ASPARAGINE
O
H2N CH C OH
CH2
C O
NH2

Asparagine
Asn, N

52
ASPARAGINE

53
 ASPARAGINE
O
H2N CH C OH Chemical formula C4H8N2O3

CH2 Molar mass 132.12 g·mol

−1

C O Appearance white crystals

NH2 Melting point 234 °C (453 °F)

Asparagine Boiling point 438 °C (820 °F;)

Asn, N

54
 R = amide
O
Chemical formula C5H10N2O3
H2N CH C OH
−1 CH2
Molar mass 146.15 g·mol
CH2
Melting point around 185°C
C O
Boiling point 445.6 °C NH2

Glutamine
Glu, Q
55
 R = amide
O
O
H2N CH C OH
H2N CH C OH
CH2
CH2
CH2
C O
C O
NH2
NH2

56
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
 R = acidic
O O

H2N CH C OH H
N
2 C
HCO
H
C
H
2
CH2
C
H
2
C O
C
O
OH
O
H
 ASPARTIC ACID
O
H2N CH C OH
CH2
C O
Auguste-Arthur
OH Plisson and Étienne
Ossian Henry discovered it
Aspartic acid on 1827 from the isolated
Asp, D
asparagus juice by heating
using lead hydroxide.
Possible sources:
Origin: Greek ; “Asparagos”
Nonessential
meat, egg, soy beans,
nuts
 GLUTAMIC ACID
O The acid was discovered by the
German chemist Karl Heinrich
H
N
2 C
HCO
H Ritthausen who treated
wheat gluten with sulfuric acid.
C
H
2

C
H
2

C
O
O
H

Glutamic acid,
Glu, E

Nonessential Possible sources:

meat, egg, soy beans, nuts
 GLUTAMIC ACID
“Kombu Broth”

Kikunae Ikeda identified

brown crystals left behind
after the evaporation of a
large amount
of kombu broth as
glutamic acid

Glutamic acid
 R = acidic
O O

H2N CH C OH N
H
2 H
CCH
O
H
C
CH2 2

H
C
2
C O
C
O
OH
H
O
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
 R = basic
O O O
H2N CH C OH H
N
2CH
COHH
2 HCO
NC H
CH2 C
H
2 C
H2

CH2 C
H
2
N
CH2 C
H
2
N
H
CH2 N
H
NH2 C
NH
N
H
2

64
 ARGININE
O
H2N CH C OH
CH2
CH2
CH2
CH2
It was isolated by Swiss
NH2 chemist Ernst Schulze in 1886
Arginine from extracts of etiolated
Arg, R seedlings. He decided this
name because of the silvery
Origin: Anc Greek; “argiros” – “silver” Possible sources:
meat, egg, soy beans, nuts
white appearance of the
Conditional
________ nitrate.
 LYSINE
O
H
N
2CH
COH
C
H
2

C
H
2

C
H
2

N
H
C
NH
N
H
2
It was isolated in 1889 by German
Lysine dentist Heinrich Drechsel who
Lys, K named it “lysatin” and later
(1891) “lysine”
Origin: Anc Greek; “lysis” – “to break up”
Possible sources: meat, egg, soy beans,milk
Conditional
 HISTIDINE
O
H
2 HCO
NC H
C
H2

N
N
H
In 1896 German biochemist
Histidine Ludwig Karl Martin
Leonard Albrecht Αlbrecht Kossel
His, H
(1853-1927) discovered and
Origin: Anc Greek; named _______ as it was
“histos” – “warp, web” initially thought that it was
“istimi” – “to stand” essential for tissue function
especially in infants.
Conditional
 R = basic
O O O
H
N
2CH
COH
H2N CH C OH H
2 HCO
NC H
C
H
2
CH2 C
H2
C
H
2
CH2 C
H
2
N
CH2 N
H
C
N
H
CH2 NH
N
H
2
NH2

68
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
 R = aromatic
O O O
H2N CH C OH H2N CH C OH H2N CH C OH
CH2 CH2 CH2

HN
OH

70
 R = aromatic
Cyclic Planar Conjugated Huckel’s Rule
(n)

Phenylalanine Yes Yes Yes 1

Tyrosine Yes Yes Yes 1

Tryptophan Yes Yes Yes 2

 TYROSINE AND PHENYLALANINE
O
O Phenylalanine
H2N CH C OH Phe, F
H2N CH C OH
CH2
CH2
Essential or not:
Molecular formula: C9H11NO3
Tyrosine Molecular weight: 181.19
Tyr, Y boiling point: 382.2 °C

OH

Essential or not:
Molecular formula: C9H11NO3
Molecular weight: 181.19
boiling point: 382.2 °C
 TRYPTOPHAN
O
H2N CH C OH
CH2

HN

Tryptophan
Trp, W
Essential or not: essential
Molecular formula: C11H12N2O2
Molecular weight: 204.23
boiling point: 447.9 °C
 R = aromatic
O O O
H2N CH C OH H2N CH C OH H2N CH C OH
CH2 CH2 CH2

HN
OH

74
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
76
PEPTIDES

77
PEPTIDES

78
79
 PEPTIDES
GLUTATHIONE (GSH)
γ-glutamylcysteinylglycine amide bond

S
H
O O O
H
N
H
O N O
H
H
N
H2 O

glutamic acid cysteine glycine

amide bond
80
INTERESTING PEPTIDES

81
INTERESTING PEPTIDES

82
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent
A.Reaction with ninhydrin

B.Reaction with biuret reagent

84
(+) towards amino acids, peptides and proteins
85
BIURET TEST

86
 O O
H 2O
R NH HN R

Cu2+
O NH HN O

R H 2O R

(+) towards molecules with ≥ 2 peptide bonds

87
 OO

H
N
2 NN
H2
Cu2+
H

biuret

88
I. STRUCTURE AND PROPERTIES OF AMINO ACIDS
A. L-amino acids
B. Zwitterionic form of amino acids
C. Amino acids with R = alkyl group
D. Amino acids with R = OH containing
E. Amino acids with R = S containing
F. Amino acids with R = amide
G. Amino acids with R = acidic
H. Amino acids with R = basic
I. Amino acids with R = aromatic
II. PEPTIDES
A. Simple Peptides
B. Interesting Peptides
III. REACTIONS OF AMINO ACIDS AND PEPTIDES
A. Reaction with ninhydrin
B. Reaction with biuret reagent