Download Natural Amino Acid CHEM 332. Spring 2014 Organic Chemistry

CHEM 332. Spring 2014
Organic Chemistry
University of Delaware
Prof. Donald Watson
Natural Amino Acid
Hydrophobic or Aliphatic Amino Acids
Me
Me
OH
H 2N
H 2N
O
Alanine
Ala
A
Me
Me
Me
OH
OH
H 2N
O
Me
Me
OH
H 2N
O
Leucine
Leu
L
Valine
Val
V
O
OH
O
OH
H 2N
HN
OH
pK a= 4.3
pK a'= 12.5
NH 2
NH
O
O
Lysine
Lys
K
Histidine
His
H
Polar/ Hydrogen bonding Amino Acids
Me
OH
OH
H 2N
pK a= 13.0
OH
O
O
Glutamine
Gln
Q
Sulfur containing Amino Acids
S Me
OH
H 2N
O
Asparagine
Asn
N
O
Methionine
Met
M
OH
H 2N
O
H 2N
NH 2
NH
O
OH
OH
OH
O
Tyrosine
Tyr
Y
Threonine
Thr
T
NH 2
H 2N
pK a= 10.1
pK a= 13.0
H 2N
O
O
Serine
Ser
S
OH
OH
H 2N
Tryptophan
Try
W
Flexible/inflexible Amino Acids
SH
OH
H 2N
O
Cysteine
Cys
C
pK a= 8.3
OH
H 2N
O
Glycine
Gly
G
N
OH
H 2N
OH
H 2N
O
Arginine
Arg
R
Glutamic acid
Glu
E
NH
pK a'= 10.5
OH
H 2N
O
Aspartic acid
Asp
D
NH 2
OH
H 2N
Phenylalanine
Phe
F
Basic Amino Acids
pK a= 3.7
O
O
O
Isoleucine
Ile
I
Acidic Amino Acids
OH
H 2N
OH
N
H
O
Proline
Pro
P
X
pK a'= 6.1