MCAT
Biochem
Ch.
1
(
Amino
Acids)
All
Amino
Acids
have?
-
ANS1.
Amino
group
(NH2)
2.
Carboxyl
group
(COOH)
3.
H
group
4.
R
group
*
the
r
group
determines
the
chemical
property
of
the
AA
and
therefore
its
function.
y-aminobuteric
acid
(GABA)
-
ANS-
neurotransmitter
-
the
amino
group
is
on
the
gamma
carbon,
3
carbons
away
from
the
carboxyl
group.
Proteinogenic
amino
acids
-
ANS20
alpha
amino
acids
encoded
by
the
human
genetic
code
Stereochemistry
of
AA
-
ANS-
all
aa
are
chiral
(optically
active)
EXCEPT
for
glycine.
-
all
aa
in
eukaryotes
are
L-amino
acid,
meaning
the
amino
group
is
on
the
left
side
of
the
fisher
projection.
-
therefore,
all
AA
have
S
absolute
config.
EXCEPT
for
cysteine
which
has
an
R
config.
b/c
the
-CH
₂
SH
has
priority
over
the
-COOH
group.
Nonpolar,
Nonaromatic
Side
Chains
(7)
-
ANS-
hydrophobic,
found
in
the
interior
of
proteins
-
Glycine,
Gly,
G
-
Alanine,
Ala,
A
-
Valine,
Val,
V
-
Leucine,
Leu,
L
-
Isoleucine,
Ile,
I
-
Methionine,
Met,
M
-
Proline,
Pro,
P
Glycine,
Gly,
G
-
ANS
Alanine,
Ala,
A
-
ANS
Valine,
Val,
V
-
ANS
Leucine,
Leu,
L
-
ANS
Isoleucine,
Ile,
I
-
ANS
Methionine,
Met,
M
-
ANSSulfur
atom,
but
the
methyl
group
makes
it
nonpolar
Proline,
Pro,
P
-
ANS-
the
ring
constraints
flexibility
of
proline.
Polar
Uncharged
R
Groups
(
5)
-
ANS-
hydrophillic
-
OH
group
in
serine
(Ser,
S)
and
threonine
(Thr,
T)
makes
them
highly
polar
and
able
to
participate
in
H
bonding -
cysteine
(Cys,
C)
has
thiol
(-SH)
group.
Sulfur
is
less
electronegative
than
O,
and
so
S-H
is
weaker
than
O-H,
leaving
the
S-H
prone
to
oxidation.
-
Asparagine
(Asn,
A)
and
glutamine
(
Gln,
Q)
have
amide
side
chains
(O=C-NH
₂
),
in
which
the
N
group
does
not
gain
or
lose
protons
with
changes
to
pH
as
does
the
amide
group.
Serine,
Ser,
S
-
ANS
Threonine,
Thr,
T
-
ANS
Cysteine,
Cys,
C
-
ANSR
config.
since
since
S
has
higher
priority
than
O
in
.
pKa
of
R
group=
8.18
Asparagine,
Asn,
N
-
ANS
Glutamine,
Gln,
Q
-
ANS
Aromatic
Side
Chains,
Uncharged
(3)
-
ANS-
Phenylalanine,
Phe,
F
-
Tyrosine,
Tyr,
Y
-
Tryptophan,
Trp,
W
Phenylalanine,
Phe,
F
-
ANSnonpolar,
benzyl
side
chain,
smallest
Tyrosine,
Tyr,
Y
-
ANSrelatively
polar
due
to
OH
-
pKa
of
R
group
10.07
Tryptophan,
Trp,
W
-
ANSlargest,
double-ring
with
N.
Positively
charged
R
groups
(Basic)
(3)
-
ANSLysine,
Lys,
K
Arginine,
Arg,
R
Hisitidine,
His,
H
Lysine,
Lys,
K
-
ANS-terminal
primary
amino
group
-
pKa
of
R
group
10.53
Arginine,
Arg,
R
-
ANS3
N
atoms
in
side
chain.
the
positive
charged
is
delocalized
over
all
3
N
atoms.
-
pKa
of
R
group
=
12.48
Histidine,
His,
H
-
ANS-
aromatic
ring
w/
2
N
atoms.
Ring
is
called
imidazole.
pKa
of
side
chain
is
relatively
close
to
6,
while
the
pka
itself
is
7.4
so
at
physiological
pH,
1
N
is
protonated
while
the
other
isn't.
-
under
acidic
conditions,
the
second
N
atom
is
protonated,
giving
side
chain
a
+
charge.
-
pKa
of
R
group
6.00