Amino acids

Amino acids: Compounds

C
that contain both an amino
group and a carboxyl
group.
-amino acid consists of:
Central carbon atom (
carbon)
Amino group
Carboxylic acid group
Hydrogen atom
Distinctive R group
(side chain).

Amino acids 1
 Chirality of Amino Acids
the natural
occurring f
Most -amino acids are COO- COO-
chiral; with two mirror- H NH3 + +
H3N H

image forms (L and D CH3 CH3

isomer) exist D-Alanine L-Alanine

 Gly has no chiral center

CHO CHO
 Ile and Thr has twothe naturally
H OH HO H
occurring form
centers CH2 OH CH2 OH
 Only the L amino acids D-Glyceraldehyde L-Glyceraldehyde
are constituents of
proteins.

Amino acids 2
 Polarity of R groups (side chains)

Amino acids 3
 Non Polar aliphatic Amino acids

Amino acids 4
 Nonpolar Aromatic amino acids

Indole ring

Amino acids 5
 Aromatic Amino Acids Absorb UV Light

Light absorption is
maximum at 280 nm for
Tryptophan and at 276
nm for Tyrosine, while
Phenylalanine absorbs
light less strongly and at
shorter wavelengths.
The absorption of light
at 280 nm can be used to
estimate concentration of
protein in solution.

Amino acids 6
 Polar Neutral Side Chains

Functions related to AA with Polar

Neutral Side Chains:
Types of Polar
Neutral Side Chains  Participate in H bonding

OH containing Form phosphate esters

Amid containing Site of carbohydrate attachment

Sulfur - containing Bond with Metal ions

Amino acids 7
 OH containing amino acids (Ser, Thr)

• OH group can be
Phosphorylated (mechanism for regulation of
activity)
• Is site for attachment of carbohydrates

Amino acids 8
 Sulfur containing R groups: Cysteine

The sulfhydryl group

is very reactive
 Oxidation of Cys
form disulfide bridge
with a covalent bond.
this is important in
stabilizing structure of
proteins

Amino acids 9
 Amid containing R groups

Very polar but non ionic

Form H bonding with
other amino acid side
chains of proteins and
contribute to its stability

Amino acids 10
 Acidic side chains: aspartic and glutamic acid

Have COOH in side chain

Called Aspartate and
Glutamate (emphasize side
chains are negatively charged
at physiological pH).
Forms ionic bonds with other
basic amino acids such as Arg
and Lys or metal ions of
proteins at physiological pH
(contribute stability)

Amino acids 11
 Polar and Basic Side Chain Amino Acids

 Highly hydrophilic (Polar)

 Positively charged at neutral pH
Examples:
Arginine has a guanidinium group.
Histidine has imidazole group (an
aromatic ring that can be positively
charged).
 Histidine often found in active
sites of enzymes,(where the
imidazole ring can bind and release
protons in the course of enzymatic
reactions).

Amino acids 12
 Uncommon amino acids

HO I I
OH
+
H3 N COO- HO O COO-
+
+ N COO-
N H3 N H3 +
H H I I
Hydroxylysine Hydroxyproline Thyroxine

•OH lysine and OH proline found in connective

tissues such as collagen.
•Thyroxine found in thyroid gland

Amino acids 13
 Uncommon amino acids and their functions

• Phosphorylation of OH groups of Ser, Thr, Tyr (Are

important in regulation of activity of proteins)
• Addition of carbohydrate or lipid (Ser, Thr, Asn)
-carboxyglutamic acid in prothrombin (binds Ca++ )
• D-alaine (bacterial cell walls)
• L-ornithine (urea cycle)
• Adrenalin (phenylalanine precursor) is neurotransmitter

• Taurine in bile salts

Amino acids 14