amino acids

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1
Glycine
GLY
Aliphatic, hydrophobic
R= H
Prefer an environment within a protein shielded from water
2
Alanine
ALA
Aliphatic, hydrophobic
R= -CH3
Prefer an environment within a protein shielded from water
3
Valine
VAL
Aliphatic, hydrophobic

CH3
|
R= -CH3
|
CH3
Prefer an environment within a protein shielded from water
4
Leucine
LEU
Aliphatic, hydrophobic

CH3
|
R= -CH2-CH3
|
CH3
Prefer an environment within a protein shielded from water
5
Isoleucine
ILE
Aliphatic, hydrophobic

CH3
|
R= CH-CH2-CH2-CH3
Prefer an environment within a protein shielded from water
6
Proline
PRO
Aliphatic, hydrophobic

CH2
/ \
CH2 CH2
| |
R= +H3N --- C-COO-
|
H
Mainly aliphatic but difficult to fit into category, mainly hydrophobic
Prefer an environment within a protein shielded from water
7
Serine
SER
Hydroyl
R=CH2OH
Hard to ionize (very high Pka)
Relevant to enzyme mechanism
8
Threonine
THR
Hydroyl
OH
|
R= -CHCH3
9
Cysteine
CYS
Sulfur R groups
R= CH2SH
Weakly polar, generally hydrophilic
Sulfhydryl group is ionizable
10
Methionine
MET
Sulfur R groups
R= -CH2-CH2-S-CH3
Weakly polar, generally hydrophilic
11
Phenylalanine
PHE
Aromatic
R= benzene
Hydrophobic
12
Tyrosine
TYR
Aromatic
R= benzene - OH
Some hydrophobic character but tempered by polar OH groups in side chain
Can be ionized at high pH
13
Tryptophan
TRP
Aromatic
R= SEE NOTES
14
UV abs.
TRP, TYP & PHE conjugated rings exhibit strong UV abs.
A280 (TYR, TRP) + A260 (PHE)
(A280 responsible for most UV absorbance in proteins)
15
Lysine
LYS
Basic
R= -CH2CH2CH2-NH3+
pKa2 ~9
Positively charged at physiological pH
16
Arginine
ARG
Basic
R= -CH2CH2CH2-NH-C-NH2
||
NH2+
pKa2 ~9
Positively charged at physiological pH
17
Histidine
HIS
Basic (less basic than LYS and ARG)
R= SEE NOTES
pKa imidazole = 6.5-7.4
pKa free a.a. ~6
pKa in proteins ~7
Side chain can exchange protons near physiological pH. Often it plays role in enzymatic mechanisms
18
Basic a.a. properties
strongly polar. Found on exterior surfaces of proteins. They are hydrated with surround aqueous environment
19
Aspartic Acid
ASP
Acidic
O
||
R= -CH2C-O-
pKa2 ~4
Carry negative charge @pH 7
Only if pH < pKa, carboxyl groups neutralized, becomes aspartate
Tend toward protein surface + in contact with water
20
Asparginine
ASN
Acidic
O
||
R= -CH2-C-NH2
Unlike acidic analog, have uncharged side chains though decidedly polar
Like acidic analog tend toward protein surface + in contact with water
21
Glutamic Acid
GLU
Acidic
O
||
R= -CH2-C-O-
pKa2 ~4
Carry negative charge @pH 7
Only if pH < pKa, carboxyl groups neutralized, becomes glutamate
Tend toward protein surface + in contact with water
22
Glutamine
GLN
O
||
R= -CH2-C-NH2
Unlike acidic analog, have uncharged side chains though decidedly polar
Like acidic analog tend toward protein surface + in contact with water
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