Amino Acids, Peptides,

and Proteins.
Classification of Amino Acids
 Fundamentals

While their name implies that amino acids are

compounds that contain an NH2 group and a
CO2H group, these groups are actually
present as NH3+ and CO2 respectively.
They are classified as a, b, g, etc. amino acids
according the carbon that bears the nitrogen.
 Amino Acids

+
NH3 an a-amino acid that is an
intermediate in the biosynthesis
a
CO2
of ethylene

+ a b-amino acid that is one of

the structural units present in
H3NCH2CH2CO2
b coenzyme A

+ a g-amino acid involved in

H3NCH2CH2CH2CO2 the transmission of nerve
g impulses
 The 20 Key Amino Acids

More than 700 amino acids occur naturally, but

20 of them are especially important.
These 20 amino acids are the building blocks of
proteins. All are a-amino acids.
They differ in respect to the group attached to
the a carbon.
These 20 are listed in Table 27.1 (p 1054-1055).
 Table 27.1

H O
+
H3N C C O

The amino acids obtained by hydrolysis of

proteins differ in respect to R (the side chain).
The properties of the amino acid vary as the
structure of R varies.
 Table 27.1

H O
+
Glycine H3N C C O
(Gly or G)
H

Glycine is the simplest amino acid. It is the only

one in the table that is achiral.
In all of the other amino acids in the table the a
carbon is a stereogenic center.
 Table 27.1

H O
+
H3N C C O

CH3

Alanine
(Ala or A)
 Table 27.1

H O
+
H3N C C O

CH(CH3)2

Valine
(Val or V)
 Table 27.1

H O
+
H3N C C O

CH2CH(CH3)2

Leucine
(Leu or L)
 Table 27.1

H O
+
H3N C C O

CH3CHCH2CH3

Isoleucine
(Ile or I)
 Table 27.1

H O
+
H3N C C O

CH3SCH2CH2

Methionine
(Met or M)
 Table 27.1

H O
+
H2N C C O

H2C CH2
C
H2

Proline
(Pro or P)
 Table 27.1

H O
+
H3N C C O

CH2

Phenylalanine
(Phe or F)
 Table 27.1

H O
+
H3N C C O

CH2

Tryptophan
N (Trp or W)
H
 Table 27.1

H O
+
H3N C C O

H2NCCH2

Asparagine
(Asn or N)
 Table 27.1

H O
+
H3N C C O

H2NCCH2CH2

Glutamine
(Gln or Q)
 Table 27.1

H O
+
H3N C C O

CH2OH

Serine
(Ser or S)
 Table 27.1

H O
+
H3N C C O

CH3CHOH

Threonine
(Thr or T)
 Table 27.1

H O
+
H3N C C O

OCCH2

Aspartic Acid
(Asp or D)
 Table 27.1

H O
+
H3N C C O

OCCH2CH2

Glutamic Acid
(Glu or E)
 Table 27.1

H O
+
H3N C C O

CH2

Tyrosine
(Tyr or Y)

OH
 Table 27.1

H O
+
H3N C C O

CH2SH

Cysteine
(Cys or C)
 Table 27.1

H O
+
H3N C C O
+
CH2CH2CH2CH2NH3

Lysine
(Lys or K)
 Table 27.1

H O
+
H3N C C O

CH2CH2CH2NHCNH2
+ NH2

Arginine
(Arg or R)
 Table 27.1

H O
+
H3N C C O

CH2

N NH

Histidine
(His or H)
 27.2
Stereochemistry of Amino Acids
 Configuration of a-Amino Acids

Glycine is achiral. All of the other amino acids

in proteins have the L-configuration at their a
carbon.

CO2
+
H3N H

R
 27.7
Peptides
 Peptides

Peptides are compounds in which an amide

bond links the amino group of one a-amino acid
and the carboxyl group of another.
An amide bond of this type is often referred to
as a peptide bond.
 Alanine and Glycine

H O H O
+ +
H3N C C O H3N C C O

CH3 H
 Alanylglycine

H O H O
+
H3N
C C N C C O

CH3 H H

Two a-amino acids are joined by a peptide bond

in alanylglycine. It is a dipeptide.
 Alanylglycine

H O H O
+
H3N
C C N C C O

CH3 H H
N-terminus C-terminus
AlaGly
AG
 Alanylglycine and glycylalanine are
constitutional isomers

H O H O
+ Alanylglycine
H3N
C C N C C O AlaGly
AG
CH3 H H

H O H O
+ Glycylalanine
H3N GlyAla
C C N C C O
GA
H H CH3
 Alanylglycine

H O H O
+
H3N
C C N C C O

CH3 H H

The peptide bond is

characterized by a
planar geometry.
 Higher Peptides

Peptides are classified according to the number

of amino acids linked together.
dipeptides, tripeptides, tetrapeptides, etc.
Leucine enkephalin is an example of a
pentapeptide.
 Leucine Enkephalin

TyrGlyGlyPheLeu
YGGFL
 Oxytocin

4 5
3
IleGlnAsn C-terminus
2
Tyr CysProLeuGlyNH2
6 7 8 9
1
Cys S S
N-terminus
Oxytocin is a cyclic nonapeptide.
Instead of having its amino acids linked in an
extended chain, two cysteine residues are
joined by an SS bond.
 Oxytocin

SS bond

An SS bond between two cysteines is

often referred to as a disulfide bridge.