Amino Acids

*Know how to draw all

20 Amino Acid
structures from pH 0-14
for first midterm

Amino acids are the building blocks of proteins

C-terminus

N-terminus
Peptide:
series of amino
acid residues
(Residue means
its not the full
amino acid)

amino acid residue

peptide bond

H2O

-most of any protein is nonpolar

nonpolar interior

-in an aqueous environment peptides

have evolved to change shaoe

globular protein

Amino acids

C
-pka depends
on R group

L-amino acid

D-amino acid

19/20

pka is the tendency of a weak acid --> H+

1/20

R-groups

asparagine
N

glutamine
Q

serine
S

threonine
T

glycine
G
H

CH2

CH2

CH2

H C OH

C O

CH2

OH

CH3

NH2

C O
NH2

aspartic acid glutamic acid

has 1
D
E more
ch2

lysine
K

arginine
R

group

(CH2)3

Ionizable
acidic

CH2

CH2

CH2

C O

CH2

O-

C O
O-

CH2
CH2

NH3+

(4.2)

CH2 H
N
C

NH

CH2

(3.9)

histidine
H

NH2+

HC

*hydrophobic

CH2
C H
H3C CH3

isoleucine
I

NH2
(12.5)

(6.0)

CH
H3C CH3

CH3

alanine
A
CH3

methionine
M
CH2
CH2
S
CH3

phenylalanine
CH2
F

CH2
C
N
H

cysteine
C
CH2
SH

CH

N
H

valine
V

H C CH3
CH2

CH2

(10.5)

leucine
L

tyrosine
Y

(8.3)
OH

magic
7
either
grab or
donate
proton

(10.1)

proline
P
COO+ CH
H2N
CH2
H2C

CH2

tryptophan
W
predominant form at pH 7, except for histidine

Other amino acid properties:

1. Glycine does not rotate plane
polarized light
2. Three amino acids absorb
UV light

W>Y>F

3. Cysteine side chain reacts with O2

Cystine

disulfide exchange reaction

intermolecular reaction

CH2-SH
HO

1. faster

OH

intramolecular reaction

2. use a smaller concentration

CH2-SH
Dithiothreitol (DTT)

thermodynamically stable

In vivo

electron transport chain

outer membrane

cytosol

plasma membrane

inner membrane
mitochondrion

Cells use glutathione (E-C-G), NADPH and

enzymes to keep SH