128

PANEL 31: The 20 Amino Acids Found in Proteins

THE AMINO ACID

The a-carbon atom is asymmetric, which

allows for two mirror image (or stereo-)
isomers, L and D.

OPTICAL ISOMERS

The general formula of an amino acid is

a-carbon atom

H
amino
group H2N

carboxyl

COOH group

H
COO

NH3+

side-chain group
L

R is commonly one of 20 different side chains.

At pH 7 both the amino and carboxyl groups
are ionized.
H
+
H3N C COO
R

COO

NH3+

Ca

Ca

Proteins consist exclusively of L-amino acids.

FAMILIES OF
AMINO ACIDS

BASIC SIDE CHAINS

The common amino acids

are grouped according to
whether their side chains
are
acidic
basic
uncharged polar
nonpolar

lysine

arginine

histidine

(Lys, or K)

(Arg, or R)

(His, or H)

CH2

CH2

CH2

CH2
C

CH2

CH2

These 20 amino acids

are given both three-letter
and one-letter abbreviations.

CH2
+
NH3

Thus: alanine = Ala = A

This group is
very basic
because its
positive charge
is stabilized by
resonance.

HN

CH2

HC

NH

NH+

These nitrogens have a

relatively weak affinity for an
H+ and are only partly positive
at neutral pH.

C
+H N
2

CH

NH2

PEPTIDE BONDS
Amino acids are commonly joined together by an amide linkage,
called a peptide bond.
H

H
N
H

C
R

O
C

N
OH

H2O

C
H

Peptide bond: The four atoms in each gray box form a rigid
planar unit. There is no rotation around the CN bond.

N
OH

R
N

O
C
OH

SH
Proteins are long polymers
of amino acids linked by
peptide bonds, and they
are always written with the
N-terminus toward the left.
The sequence of this tripeptide
is histidine-cysteine-valine.

amino- or
N-terminus

+H N
3

CH2

HC

N
H

C
O

CH
NH+

carboxyl- or
C-terminus

COO

CH
CH3

C
HN

CH2

CH3

These two single bonds allow rotation, so that long chains of

amino acids are very flexible.

THE SHAPE AND STRUCTURE OF PROTEINS

129

ACIDIC SIDE CHAINS

NONPOLAR SIDE CHAINS

alanine

valine

aspartic acid

glutamic acid

(Ala, or A)

(Val, or V)

(Asp, or D)

(Glu, or E)

O
C

CH2

CH3

CH2

CH

CH3

CH3

CH2

C
O

leucine

C
O

(Leu, or L)
H

CH2

CH3

CH

CH3

CH

UNCHARGED POLAR SIDE CHAINS

CH3

CH2
CH3

asparagine

glutamine

proline

phenylalanine

(Asn, or N)

(Gln, or Q)

(Pro, or P)

(Phe, or F)

CH2

CH2

NH2

C
CH2

CH2

CH2

C
O

CH2

CH2

(actually an
imino acid)

C
O

NH2

Although the amide N is not charged at

neutral pH, it is polar.

methionine

tryptophan

(Met, or M)

(Trp, or W)

CH2

CH2

CH2
S

serine

threonine

tyrosine

(Ser, or S)

(Thr, or T)

(Tyr, or Y)

CH2
OH

CH

CH3

CH3

N
H

glycine

cysteine

(Gly, or G)

(Cys, or C)

CH2

OH

OH
The OH group is polar.

CH2
SH

Disulfide bonds can form between two cysteine side chains

in proteins.
CH2

CH2