Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1 Amino acid:

acid a compound that contains
both an amino group, -NH2 and a
-amino acid
carboxyl group, -COOH
20 amino acids H
Naming CH3CH2 C COOH
Zwitterion NH2
Isoelectric point -amino acid: an amino acid in which
the amino group is on the carbon
Structures in:
adjacent to the carboxyl group
H
Acidic

NH2 C COOH
Basic
pI CH2CH3
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
20 amino acids Glycine
Naming Gly
Zwitterion
Alanine H3C CH COOH
Isoelectric point
Ala NH2
Structures in: CH3
Valine
Acidic Val HC CH COOH

Basic CH3 NH2

pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
CH3
20 amino acids Leucine
CH COOH
Naming Leu CHCH2

CH3 NH2

Zwitterion
Isoleucine CH3CH2CH CH COOH
Isoelectric point Ile CH3
NH2
Structures in:
Phenylalanine
Acidic Phe CH2 CH COOH
NH2
Basic
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
OH
20 amino acids Threonine
CH3 C CH COOH
Naming Thr
H NH2
Zwitterion CH2 CH2 COOH
Cysteine
Isoelectric point C
Cys CH2 NH
Structures in: H
Methionine HO CH2 CH COOH
Acidic
Met
Basic NH2
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
O
20 amino acids Tryptophan
OH
Naming Trp NH2
NH
Zwitterion CH2 CH2 COOH
Proline
Isoelectric point C
Pro CH2 NH
Structures in: H
Serine HO CH2 CH COOH
Acidic
Ser
Basic NH2
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
Threonine OH
20 amino acids CH3 C CH COOH
Thr
Naming
H NH2
Zwitterion
Cysteine HS CH2 CH COOH
Isoelectric point Cys NH2
Structures in:
Methionine CH S CH CH CH COOH
3 2 2
Acidic
Met NH2
Basic
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
20 amino acids Tyrosine HO CH2 CH COOH
Naming Tyr NH2

Zwitterion
Asparagine NH2─C─CH2─CH ─COOH
Isoelectric point ║ │
Asn O NH2
Structures in:
Glutamine NH2─C─CH2CH2─CH─COOH
Acidic
Gln ║
O
│
NH2
Basic
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
Aspartic HOOC─CH2─CH─COOH
20 amino acids
acid │
Naming NH2
Asp
Zwitterion
Glutamic HOOC─CH2CH2─CH─COOH
Isoelectric point acid │
NH2
Structures in: Glu
Acidic Lysine H2N─CH2CH2CH2CH2─CH ─COOH
Basic Lys │
NH2
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1
Name Structure
-amino acid
Arginine H N─C─NH─(CH2) ─CH─COOH
2 3
20 amino acids │ │
Arg NH NH
Naming 2

Zwitterion Histidine HC─C=CH2─CH ─ COOH

His │ │ │
Isoelectric point N NH NH2
Structures in:
CH
Acidic
Basic
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1 IUPAC Name

i) H
-amino acid
H C COOH 2-amino ethanoic acid
20 amino acids 2 1
NH2
Naming
Zwitterion ii) CH3
3

Isoelectric point H C COOH 2-amino propanoic acid

2 1
Structures in: NH2

iii) CH2OH
Acidic 3
H C COOH 2-amino-3-hydroxy
Basic 2 1
propanoic acid
NH2
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1 IUPAC Name

-amino acid CH2CH2CH2NH2
iv) 3 4 5
20 amino acids H C COOH
2 1
Naming
NH2 2,5-diamino pentanoic acid
Zwitterion
Isoelectric point
v) CH2CH2CH2COOH
Structures in: 3 4 5 6
H C COOH
2 1
Acidic
NH2
Basic 2-amino hexanedioic acid
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1 Zwitterion
-amino acid Amino acids can undergo an
internal acid-base reaction, in which a
20 amino acids proton is transferred from the
Naming carboxyl (-COOH) to the amino group
(-NH2) to form dipolar ion called
Zwitterion
zwitterion.
Isoelectric point
CH2CH2CH3 CH2CH2CH3
Structures in:
H C COOH H C COO-
Acidic NH2 +
NH3
Basic
(neutral) (dipolar ion @
pI zwitterion)
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.1 Isoelectric Point (pI)

-amino acid In general, zwitterion is electrically
20 amino acids neutral and exists at specific pH
Naming This particular pH is called isoelectric
points
Zwitterion
Each amino acid has it’s specific pI
Isoelectric point Lysine H2N─(CH2)4─CH ─COOH 9.7
Example: │
Structures in:
(Lys) NH
Amino Acid Structure2 pI
Acidic
Aspartic HOOC─CH2─CH─COOH 2.9
Glycine
acid 6.1
│
Basic (Gly) NH2
(Asp)
pI
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

In Acidic
20.1 The cation, H3N+— CH2 — COOH
-amino acid predominates (Amino acids as base)
c
In Basi
20 amino acids The anion, H2N— CH2 — COO-
Naming predominates (Amino acids as acid)
In pI
Zwitterion The zwitterion, H3N+—CH2—COO-
Isoelectric point predominates (Amino acids as
amphoteric)
Structures in: NH2CH2COOH
Gly (pI = 6.1)
Acidic + - -
+
NH3CH2COOH ↔NH3CH2COO ↔ NH 2 CH 2 COO
Basic
pI at pH < 6.1 at pH = 6.1 at pH > 6.1
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 a) Reaction with HCl

Reactions of R' R' _
+
–NH2 group: R C NH2 + HCl R C NH3Cl
COOH COOH
HCl
HNO2
Example:
Reactions of CH2CH3 CH2CH3
-COOH group: + _
H C NH2 + HCl H C NH3Cl
NaOH COOH COOH
ROH
Peptide bond
Importance
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 b) With Nitrous Acid (HNO2)

R' R'
Reactions of NaNO2 / HCl +
R C NH2 R C N N
–NH2 group: -5 to 0 C o
COOH COOH
HCl diazonium ion
HNO2 elimination of N2(g)

Observation: Bubbling R'

Reactions of
of gas (N2)
-COOH group: R C+

NaOH COOH
carbocation
ROH H 2O - +
+ Cl -H
Peptide bond 2-hydroxy halocarboxylic Alkenoic
carboxylic acid acid acid
Importance
Chapter 20 : Amino Acids and Proteins

Example: CH3 CH3

NaNO2 / HCl +
H C NH2 H C N N
COOH COOH
diazonium ion
elimination of N2(g)
CH3
H C+
COOH
carbocation
+
H 2O - -H
+ Cl
CH3
CH3 CH2
H C OH
H C Cl H C
COOH
COOH COOH
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 c) Reaction with NaOH

Reactions of R' R'
–NH2 group: R C NH 2 + NaOH R C NH2
_
COOH COO Na+
HCl
HNO2
Example:
Reactions of
CH2CH3 CH2CH3
-COOH group:
H C NH2 + NaOH H C NH2
NaOH _
COOH COO Na+
ROH
Peptide bond
Importance
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 d) Reaction with ROH + HCl (catalyst)

Reactions of R' R'
–NH2 group: R C NH 2 + R''OH R C NH2 + H 2O
COOH COOR''
HCl
HNO2
Example:
Reactions of
CH2CH3 R'
-COOH group: HCl
H C NH 2 + CH3OH R C NH2 + H 2O
NaOH
COOH COOR''
ROH
Peptide bond
Importance
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 Peptide Bond

Reactions of 2 amino acids react together, H2O
–NH2 group: is eliminated.
This is condensation reaction.
HCl
Peptides are amino acid polymers
HNO2 in which the individual amino acid
Reactions of units, are linked together by amide
-COOH group: bonds, or peptide bonds
NaOH •2 amino acids form dipeptide
ROH •3 amino acids form tripeptide
•15 – 30 amino acids form oligopeptide
Peptide bond •> 30 amino acids form polypeptide
Importance
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 Formation of dipeptide bond:

O H
Reactions of
–NH2 group: H2N CH2 C OH + H N C COOH
H CH3
HCl
HNO2 Notes:
O H

Reactions of H2N CH2 C N C COOH + H O

N-terminal (with free –NH2) 2is
-COOH group: H CH3
always written on the left and C-
NaOH terminal
amide (with
bond /free –COOH) at the
right side bond
peptide
ROH
Peptide bond A dipeptide

Importance
Chapter 20 : Amino Acids and Proteins

Formation of tripeptide bond:

O H CH2 OH
H2N CH2 C OH H N C COOH H N C COOH
H CH3 H H
Gly Ala Tyr

Write the structural formula of tripeptide with the following

sequence Gly-Ala-Tyr :

O H O CH2 OH
H2N CH2 C N C C N C COOH
H CH3 H H

A tripeptide
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 Importance of amino acids :

Reactions of  Human beings can synthesize about half
–NH2 group: of the amino acids needed to make
proteins.
HCl
 Other amino acids, called the essential
HNO2 amino acids,
acids must be provided in the diet.
Reactions of
-COOH group:  The ten essential amino acids are :
NaOH
arginine (Arg) valine (val) methionine (Met)
ROH threonine (Thr) leucine (Leu) phenylalanine (Phe)
histidine (His) isoleucine (Ile) lysine (Lys)
Peptide bond trypthophan (Trp)
Importance
Chapter 20 : Amino Acids and Proteins

20.1 : Introduction 20.2 : Chemical Properties

20.2 Importance of proteins :

Reactions of  Proteins are the most abundant organic
–NH2 group: molecules in animals, playing important
roles in all aspects of cell structure and
HCl function.
HNO2  Examples of protein functions :
Reactions of
Class of protein Examples Functions
-COOH group:
structural protein collagen, keratin tendons, skin
NaOH
hair, nails
ROH
enzymes DNA polymerase repair DNA
Peptide bond
transport protein hemoglobin transport O2
Importance