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Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Functional
Group
Structural
Formula
OH
Hydroxyl
Found
In
Example
H
H
C
C
H
carbohydrates,
proteins,
nucleic
acids,
lipids
OH
H H
Ethanol
O
Carbonyl
H
C
C
C
carbohydrates,
nucleic
acids
H
H
C
H
proteins,
lipids
C
OH
H
Acetic acid
H
N
O
C
OH
Amino
O
H
Acetaldehyde
O
Carboxyl
H
HO
O
H
C
C
H
H
proteins,
nucleic
acids
N
H
CH3
Alanine
COOH
Sulfhydryl
S
H
H
C
CH2
S
H
proteins
NH2
Cysteine
O–
Phosphate
O
OH OH H
O– H
P
O
C
C
C
H
H
H
O
O
P
O–
nucleic
acids
O–
Glycerol phosphate
H
Methyl
C
H
H
HO
O
H
C
C
NH2
H
C
H
H
Alanine
proteins
1
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
X
W
X
C
Z
W
C
Y
Y
Z
Mirror
2
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Cellular Structure
Polymer
Monomer
Carbohydrate
CH2OH
O
H
H
OH
HO
H
Starch grains in a chloroplast
Starch
OH
Monosaccharide
P
P
Nucleic Acid
G
P
T
A
P
Nitrogenous base
P
T
G
A
C
P
P
P
P
C
p
A
P
P
A
T
C
P
Chromosome
P
P
P
O
Phosphate
group
5-carbon sugar
OH
DNA strand
Nucleotide
CH3
Protein
H
Ala
Val
Val
Intermediate filament
Sel
Polypeptide
N
Ala
H
C C
H
OH
O
Amino acid
Lipid
O H H H H H H H H H H H
HO C C C C C C C C C C C C H
H H H H H H H H H H H
Adipose cell with fat droplets
Triglyceride
Fatty acid
3
4
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
H 2O
H 2O
HO
H
HO
HO
H
H
a. Dehydration reaction
HO
HO
H
H
HO
H
b. Hydrolysis reaction
5
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
3-carbon Sugar
H
O
5-carbon Sugars
5
CH2OH
C
O
1
H
H
C
2
OH
C
OH
3
5
H
Glyceraldehyde
4
H
H
H
3
H
2
OH
CH2OH
OH
Ribose
4
H
H
5
OH
1
H
3
H
2
OH
CH2OH
6
O
OH
1
6-carbon Sugars
H
Deoxyribose
H
H
OH
4
HO
3
H
6
O
1
OH
2
OH
6
O
H
H
Glucose
CH2OH
5
HO
H
4
OH
5
H
OH
3
H
Fructose
OH
2
CH2OH
1
CH2OH
4
H
H
OH
3
H
O
OH
1
H
H
2
OH
Galactose
6
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
CH2OH
5
H
O
C
OH
H
H
1
H
C
OH
C
H
2
HO
H
C
OH
C
OH
C
OH
4
H
H
5
6
H
OH
H
C
3
H
OH
C
C2
H
OH
4
OH
H
5
C
3
H
6
C
C
O
H
O
3
O
H
OH
C
H
C2
H
OH
H
C
1
OH
α-glucose
or
β-glucose
C
1
4
C
H
5
CH2OH
C
H
C
OH
4
OH
C
3
H
H
O
H
C2
OH
C
1
H
OH
7
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
H
H
H
H
C
OH
C
O
HO
C
H
H
C
H
H
C
O
H
C
OH
H
HO
C
H
C
OH
HO
C
H
H
C
OH
H
C
OH
H
C
OH
H
C
OH
C
O
H
C
OH
HO
C
OH
H
C
OH
C
OH
H
Fructose
Structural
isomer
H
Glucose
Stereoisomer
H
Galactose
8
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
CH2OH
H
HO
H
OH
H
+
OH
CH2OH
O
O H
H
OH
α-glucose
a.
CH2OH
HO
H
H
OH
OH
H
Fructose
H
CH2OH
HO
H 2O
CH2OH
O
H
OH
H
H
CH2OH
O
H
O
OH
Sucrose
H
H
OH CH OH
2
OH
H
H
HO
O
H
OH
H
H
CH2OH
H
H
O
O
H
OH
H
OH
H
OH
H
OH
Maltose
b.
9
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
CH2OH
H
4
HO
O
H
OH
H
H
CH2OH
O
H
1
OH
H
OH
a-glucose
H
OH
H
H
OH
OH
O
H
α-1
H
H
H
OH
OH
H
H
OH
H
b.
+
Amylopectin
7.5 µm
6 linkage
α-1
H
OH
H
H
H
OH
α-1
O
CH2OH
O
Amylose
CH2OH
O H
H
H
OH
H
O
OH
H
OH
4 linkages
CH2OH
O H
H
OH
H
O
H
a.
CH2OH
O
CH2
O H
Glycogen
4 linkage
c.
3.3 µm
b: © Asa Thoresen/Photo Researchers, Inc.; c: © J.Carson/Custom Medical Stock Photo
10
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
CH2OH
H
4
HO
CH2OH
O
H
OH
H
H
OH
OH
H
1
H
O
H
O
H
OH
H
H
OH
O
H
H
OH
H
H
O
H
H
O
CH2OH
β-1
β-glucose
CH2OH
OH
O
H
OH
H
H
OH
O
H
4 linkages
a.
b.
500 µm
b: © J.D. Litvay/Visuals Unlimited
11
12
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Nitrogenous base
NH2
7N
1
O
9
P
O
5
5
8
Phosphate group
-O
6
N
4
2
N
3
CH2
O-
O
1
4
3
2
OH in RNA
OH
Sugar
H in DNA
13
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
O
NH2
5΄
5΄
1΄
4΄
3΄
P
H
C
N C C
N
N C
C H
Phosphodiester bonds
O
4΄
1΄
3΄
P
2΄
5΄
C
N C C
N
H
N C
C
NH 2
H
H
C
H
C
C
N
N
Guanine
O
NH2
2΄
5΄
N
H
H
Adenine
O
Pyrimidines
P
Purines
Phosphate group
H 3C
N
C
O
H
Cytosine
(both DNA and RNA)
H
C
C
C
N
O
N
H
H
C
C
O
H
C
H
Thymine
(DNA only)
C
N
N
H
C
O
H
Uracil
(RNA only)
b.
O
1΄
4΄
3΄
5-carbon sugar
2΄
Nitrogenous base
P
5΄
O
1΄
4΄
3΄
OH
a.
2΄
3΄
14
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Sugar–phosphate
“backbone”
P
A
P
T
G
C
Phosphodiester
bonds
T
P
OH
3΄ end
A
P
Hydrogen bonds
between
nitrogenous bases
P
5΄ end
15
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
P
P
P
G
P
T
T
P
A
Deoxyribosephosphate
backbone
G
A
C
P
P
A
C
P
P
Bases
P
P
P
C
A
P
P
Hydrogen bonding
P
occurs between base-pairs
P
G
A
T
P
DNA
P
P
Ribose-phosphate
backbone
G
P
U
A
Bases
U
P
P
RNA
G
16
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Nitrogenous base
(adenine)
NH2
O
–O
P
O–
O
O
P
O–
P
5
N1
8
O
O
6
7 N
Triphosphate group
O
5
CH2
9
N
4
N
2
3
O–
O
1
4
3
2
OH
OH
5-carbon sugar
17
18
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H
H
R
N
C
C
H
O
OH
H
H
R
N
C
C
H
O
Amino acid
OH
Amino acid
H 2O
H
H
R
N
C
C
H
O
H
R
N
C
C
H
O
OH
Dipeptide
19
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Nonpolar
Polar uncharged
CH3
H3
N+
C
C
CH3
Nonaromatic
H 3N +
CH2
H3
C
C
C
H
O
CH2
H3
CH3
C
OH
H 3N +
C
C
O–
O
H O
Threonine
(Thr)
CH3
H3
CH
H
C
C
O–
N+
C
H
O
O–
O–
N+
C
C
H
O
O–
CH2
C
CH2
H 3N +
CH2
H 3N +
H O
Glycine
(Gly)
C
C
H
O
CH2
Aromatic
H 3N +
C
C
H
O
Phenylalanine
(Phe)
Special function
H 3N +
CH2
CH2
H 3N +
C
C
O–
C
H 3N +
H O
Tryptophan
(Trp)
C
H O
Tyrosine
( Tyr)
H
O
O–
NH2
C
C
H
O
C
O–
NH2+
NH
CH2
Lysine
( Lys)
C
O–
C
CH2
CH2
NH
C
NH3+
CH2
CH2
CH
N
H
Histidine
(His)
O–
Glutamine
(Gln)
OH
NH+
HC
Aspartic acid
(Asp)
C
Asparagine
(Asn)
H O
Leucine
(Leu)
O–
NH2
O
O–
CH2
H3
C
C
C
CH2
CH3
C
N+
H O
Glutamic acid
(Glu)
C
H 3N +
C
H
NH2
O
O–
CH2
C
CH2
O–
O–
CH3
Isoleucine
(Ile)
H 3N +
C
C
H O
Serine
(Ser)
CH3
C
C
H O
Valine
(Val)
CH3
C
O–
CH2
H 3N +
CH
N+
O
OH
O–
H O
Alanine
(Ala)
H
Charged
CH2
CH2
O–
H 3N +
C
C
O–
H O
Arginine
(Arg)
CH3
CH2
CH2
CH2
CH
NH2+
S
H
CH2
S
CH2
C
O
Proline
(Pro)
O–
H3
N+
CH2
C
C
H
O
Methionine
(Met)
O–
H 3N +
C
C
H
O
Cysteine
(Cys)
O–
20
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O
C
C
N
O
H
O
O
C
N
(CH2)4
C
H
C
C
N
C
R
R
C
C
H
R
H
S S
C
N
H
H
C
NH3+
Lonic bond
C
N
C
C
O
O–
O
O
C
Hydrogen bond
N
CH3
CH3
N
C
C
C
C
O
van der Waals
attraction
CH2
Disulfide bridge
N
C
C
O
a.
b.
CH 3
c.
d.
CH 3
H
Hydrophobic
exclusion
CH 3 CH 3
C
CH 3
CH 3
CH 2
C
CH 3
e.
21
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Primary Structure
R
C
C
H
O
H
H
O
N
C
C
R
R
N
C
C
H
H
O
H
H
N
C
R
The primary structure can fold
into a pleated sheet, or turn into a helix
Secondary Structure
Secondary Structure
β-pleated sheet
Tertiary Structure
α-helix
Quaternary Structure
22
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Misfolded
protein
Cap
Chaperone
protein
ATP
ATP + P
Correctly
folded
protein
Chance for protein to refold
23
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Properly folded protein
Denaturation
Denatured
protein
24
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Structural Formula
H
Structural Formula
H
O H H H H H H H H H H H H H H H H H
H C O C C C C C C C C C C C C C C C C C C H
O H H H H H H H
H H H H H H H H H H H H H H H H H
O H H H H H H H
O H H H H H H H H H H H H H H H H H
H
H
H H
H C O C C C C C C C C C C C C C C C C C C H
H
H H H H H H H H H H H H H H H H H
Space-Filling Model
a.
H H H H H H H H
H C O C C C C C C C C C C C C C C C C C C H
H H H H H H H H H H H H H H H H H
H
H H H H H
H H H H H H H H H H H H H H H H H
O H H H H H H H H H H H H H H H H H
H C O C C C C C C C C C C C C C C C C C C H
H
H C O C C C C C C C C C C C C C C C C C C H
H H H H H H H H H H H H H H H H H
H C O C C C C C C C C C C C C C C C C C C H
O H H H H H H H
H H H H H H H H H H H H H H H H H
Space-Filling Model
b.
25
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CH3
H 3C
CH
H 3C
CH
CH2
CH
CH2
a. Terpene (citronellol)
CH2
CH2
CH2
CH2
H 3C
CH3
OH
CH
CH2
CH3
CH
CH3
CH3
HO
b. Steroid (cholesterol)
26
Nonpolar Hydrophobic Tails
Polar Hydrophilic Heads
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CH2
N+(CH3)3
CH2
O
O P O–
Choline
Phosphate
Glycerol
F
a
t
t
y
a
c
i
d
a.
H
H 2C
C
O
O
O
CH2
C OC O
CH CH
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH
CH2 CH
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH2
CH2 CH2
CH3 CH3
F
a
t
t
y
a
c
i
d
b.
c.
d.
27
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Water
Lipid head
(hydrophilic)
Lipid tail
(hydrophobic)
a.
Water
Water
b.
28
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