Frederick A.

Bettelheim
William H. Brown
Mary K. Campbell
Shawn O. Farrell
www.cengage.com/chemistry/bettelheim

Chapter 22
Proteins
Amino Acids

William H. Brown • Beloit College

Amino Acids
Amino acid: A compound that contains both an amino
group and a carboxyl group.
• -Amino acid: An amino acid in which the amino group
is on the carbon adjacent to the carboxyl group.
• Although -amino acids are commonly written in the
un-ionized form, they are more properly written in the
zwitterion (internal salt) form.
O O
-
R-CH-COH R-CH-CO
+
NH2 NH3
Un-ionized Zwitterion
form

22-2
Chirality of -Amino Acids
With the exception of glycine, all protein-derived amino
acids have at least one stereocenter (the -carbon) and
are chiral.
• The vast majority of -amino acids have the L-
configuration at the -carbon.

COO- COO-
H N H3 + +
H 3N H
CH3 CH3
D-Alanine L-Alanine
(Fischer projections)

22-3
Chirality of -Amino Acids
A comparison of the configuration of L-alanine and D-
glyceraldehyde (as Fischer projections):
the n aturally
occu rring form
COO- COO-
H NH3 + +
H3 N H
CH3 CH3
D-A lanine L-Alan ine

CHO CHO
the n aturally
H OH HO H
occu rring form
CH2 OH CH2 OH
D -Glycerald ehyde L-Glycerald ehyde

22-4
Protein-Derived -Amino Acids
Nonpolar side chains (at pH 7.0)
COO- A lanine -
COO Phen ylalan ine
+ (A la, A) (Phe, F)
NH3 NH3 +

COO- Glycine
+ (Gly, G) COO
- Prolin e
NH3 N
H H (Pro, P)
- -
COO Isoleucin e COO Tryptoph an
(Ile, I) (Trp , W)
NH3 + NH3 +
N
-
COO Leucin e H
(Leu, L)
NH3 + -
COO Valine
-
S COO Meth ion in e (Val, V)
+
+ (Met, M) NH3
NH3
22-5
Protein-Derived -Amino Acids
• Polar side chains (at pH 7.0)
- -
H2 N COO COO
As paragine HS Cysteine
O NH3 + (As n, N ) NH3 + (Cys, C)

O
- COO-
COO Glutamine HO Serine
H2 N (Ser, S)
NH3 + (Gln, Q) NH3 +

- OH
COO
Tyrosine COO- Threon in e
NH3 + (Tyr, Y) (Thr, T)
HO NH3 +

22-6
Protein-Derived -Amino Acids
Acidic and basic side chains (at pH 7.0)
-
O COO- NH2 +
As partic acid COO-
+
O NH3 (As p, D ) H2 N N Arginin e
H NH3
+ (Arg, R)
O
-
- COO Glutamic acid
O -
COO
NH + (Glu, E)
3 N
+
Histidine
NH3 (His , H)
N
H
+
H3 N COO-
Lysine
+
NH3 (Lys, K)

22-7
Protein-Derived -Amino Acids

1. For 19 of the 20, the -amino group is primary; for

proline, it is secondary.
2. With the exception of glycine, the -carbon of each is a
stereocenter.
3. Isoleucine (left) and threonine (right) contain a second
stereocenter.

22-8
Cysteine
The -SH (sulfhydryl) group of cysteine is easily oxidized to
an -S-S- (disulfide).
+ -
H3 N-CH-COO
CH2 a disulfide
+ oxidation bon d
2 H3 N-CH-COO- S
CH2 reduction S
SH CH2
+ -
Cysteine H3 N-CH-COO
Cystine

22-9
Phe, Trp, and Tyr
The amino acids phenylalanine, tryptophan, and tyrosine
have aromatic rings on their side chains.
Tryptophan is the precursor to the neurotransmitter
serotonin.

22-10
Tyr and Phe
Phenylalanine and tyrosine are precursors to
norepinephrine and epinephrine, both of which are
stimulatory.

22-11
Other Amino Acids
Hydroxylation (oxidation) of proline, lysine, and tyrosine,
respectively and iodination for tyrosine, give these
uncommon amino acids.
O
HO
C-O -
COO- H 3N C H
N
H H
Hydroxyproline
I I
O
+ OH
H 3N COO-
I I
N H3 +
OH
Hydroxylysine
Thyroxine
22-12