the structure and function of macromolecules note sheets... · organic chemistry-the study of...
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Biochemistry
The Structure and Function of
Macromolecules
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Carbon—Backbone of
Biological Molecules
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Organic Chemistry-the study of
carbon compounds
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Carbon Molecules
MolecularFormula
StructuralFormula
Ball-and-StickModel
Space-FillingModel
Methane
Ethane
Ethene (ethylene) NOTE TAKING SHEET ONLY
Carbon Molecules
Hydrogen
(valence = 1)
Oxygen
(valence = 2)
Nitrogen
(valence = 3)
Carbon
(valence = 4)
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Carbon Skeleton Diversity
LengthEthane Propane
Butane 2-methylpropane(commonly called isobutane)
Branching
Double bonds
Rings
1-Butene 2-Butene
Cyclohexane BenzeneNOTE TAKING SHEET ONLY
Isomers
Structural isomers differ in covalent partners, as shown
in this example of two isomers of pentane.
Geometric isomers differ in arrangement about a double
bond. In these diagrams, X represents an atom or group
of atoms attached to a double-bonded carbon.
cis isomer: The two Xsare on the same side.
trans isomer: The two Xsare on opposite sides.
L isomer D isomer
Enantiomers differ in spatial arrangement around an
asymmetric carbon, resulting in molecules that are
mirror images, like left and right hands. The two
isomers are designated the L and D isomers from the
Latin for left and right (levo and dextro). Enantiomers
cannot be superimposed on each other.NOTE TAKING SHEET ONLY
Isomerism
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Structural Isomers
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Geometric Isomers
CisC
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Enantiomers
L-Dopa
(effective against
Parkinson’s disease)
D-Dopa
(biologically
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Functional Groups
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STRUCTURE
(may be written HO—)
NAME OF COMPOUNDS FUNCTIONAL PROPERTIES
.
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STRUCTURE
NAME OF COMPOUNDS
EXAMPLE
Acetone, the simplest ketone
Acetone, the simplest ketone
Propanal, an aldehyde
FUNCTIONAL PROPERTIES
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STRUCTURE
NAME OF COMPOUNDS
EXAMPLE
Acetic acid, which gives vinegar
its sour taste
FUNCTIONAL PROPERTIES
Acetic acid Acetate ion
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STRUCTURE
NAME OF COMPOUNDS
Amine
EXAMPLE
FUNCTIONAL PROPERTIES
(nonionized)
Glycine
(ionized)
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STRUCTURE
(may be written HS—)
NAME OF COMPOUNDS
EXAMPLE
Ethanethiol
FUNCTIONAL PROPERTIES
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STRUCTURE
NAME OF COMPOUNDS
EXAMPLE
Glycerol phosphate
FUNCTIONAL PROPERTIES
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Biochemistry: The Molecules of Life
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Biochemistry
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Macromolecules - Polymers
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Polymers
Short polymer Unlinked monomer
Dehydration removes a water
molecule, forming a new bond
Dehydration reaction in the synthesis of a polymer
Longer polymer
Hydrolysis adds a water
molecule, breaking a bond
Hydrolysis of a polymer
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Carbohydrates
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Sugars
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Monosaccharides
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Triose sugars
(C3H6O3)
Glyceraldehyde
Pentose sugars
(C5H10O5)
Ribose
Hexose sugars
(C5H12O6)
Glucose Galactose
Dihydroxyacetone
Ribulose
Fructose
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Monosaccharides
Glucose Fructose
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Monosaccharides
• In aqueous solutions, monosaccharides form rings
Linear and
ring forms
Abbreviated ring
structure
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Isomers of Glucose:
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33
H H HHH
H
OH OH
OHO
OH H
OHO
CH2OH
RiboseGlyceraldehyde
Triose (3-carbon sugar)
Pentoses
(5-carbon sugars)
Deoxyribose
HH
H
H
H
H
OH
OH
O
C
C
C4
5
1
3 2
4
5
1
3 2
1
3
2
CH2OH
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Disaccharides
Glucose
Maltose
Fructose Sucrose
Glucose Glucose
Dehydration
reaction in the
synthesis of maltose
Dehydration
reaction in the
synthesis of sucrose
1–4glycosidic
linkage
1–2glycosidic
linkage
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Disaccharides
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Polysaccharides
(a) Starch
(b) Glycogen
(c) CelluloseNOTE TAKING SHEET ONLY
Storage Polysaccharides - StarchChloroplast Starch
1 µm
Amylose
Starch: a plant polysaccharide
Amylopectin
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Storage Polysaccharides - Glycogen
Mitochondria Glycogen granules
0.5 µm
Glycogen
Glycogen: an animal polysaccharideNOTE TAKING SHEET ONLY
Structural Polysaccharides
a Glucose
a and b glucose ring structures
b Glucose
Starch: 1–4 linkage of a glucose monomers.
Cellulose: 1–4 linkage of b glucose monomers.NOTE TAKING SHEET ONLY
Cellulose
Cellulose
molecules
Cellulose microfibrils
in a plant cell wall
Cell walls Microfibril
Plant cells
0.5 µm
b Glucose
monomer
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Chitin
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Lipids
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Fats
Dehydration reaction in the synthesis of a fat
Glycerol
Fatty acid
(palmitic acid)
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Fatty Acids
Stearate OleateNOTE TAKING SHEET ONLY
Fats
Ester linkage
Fat molecule (triacylglycerol)NOTE TAKING SHEET ONLY
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Glycerides
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Saturated Fats
Saturated fat and fatty acid.
Stearic acid
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Unsaturated Fats
Unsaturated fat and fatty acid.
Oleic acid
cis double bondcauses bending
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Fat Sources
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Phospholipids
Structural formula Space-filling model Phospholipid symbol
Hydrophilic
head
Hydrophobictails
Fatty acids
Choline
Phosphate
Glycerol
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Micelle
Phospholipid bilayerWater
Water
Water Lipid head (hydrophilic)
Lipid tail (hydrophobic)
Phospholipids
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Phospholipids
WATERHydrophilic
head
Hydrophobic
tailsWATER
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Steroids
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Proteins
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Proteins
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Amino Acids
Amino
group
Carboxyl
group
a carbon
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O
O–
H
H3N+ C C
O
O–
H
CH3
H3N+ C
H
C
O
O–
CH3 CH3
CH3
C C
O
O–
H
H3N+
CH
CH3
CH2
C
H
H3N+
CH3
CH3
CH2
CH
C
H
H3N+ C
CH3
CH2
CH2
CH3N+
H
C
O
O–
CH2
CH3N+
H
C
O
O–
CH2
NH
H
C
O
O–
H3N+ C
CH2
H2C
H2N C
CH2
H
C
Nonpolar
Glycine (Gly) Alanine (Ala) Valine (Val) Leucine (Leu) Isoleucine (Ile)
Methionine (Met) Phenylalanine (Phe)
C
O
O–
Tryptophan (Trp) Proline (Pro)
H3C
Figure 5.17
S
O
O–
Amino Acids
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O–
OH
CH2
C C
H
H3N+
O
O–
H3N+
OH CH3
CH
C C
HO–
O
SH
CH2
C
H
H3N+ C
O
O–
H3N+ C C
CH2
OH
H H H
H3N+
NH2
CH2
O
C
C C
O
O–
NH2 O
C
CH2
CH2
C CH3N+
O
O–
O
Polar
Electrically
charged
–O O
C
CH2
C CH3N+
H
O
O–
O– O
C
CH2
C CH3N+
H
O
O–
CH2
CH2
CH2
CH2
NH3+
CH2
C CH3N+
H
O
O–
NH2
C NH2+
CH2
CH2
CH2
C CH3N+
H
O
O–
CH2
NH+
NH
CH2
C CH3N+
H
O
O–
Serine (Ser) Threonine (Thr)Cysteine
(Cys)
Tyrosine
(Tyr)Asparagine
(Asn)
Glutamine
(Gln)
Acidic Basic
Aspartic acid
(Asp)
Glutamic acid
(Glu)
Lysine (Lys) Arginine (Arg) Histidine (His)
Amino Acids
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Amino Acids and Peptide Bonds
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Protein Conformation and Function
A ribbon model
Groove
Groove
A space-filling modelNOTE TAKING SHEET ONLY
Four Levels of Protein Structure
Amino acidsubunits
b pleated sheet
a helix
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Primary Structure
Amino acidsubunits
Carboxyl end
Amino end
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Secondary Structure
Amino acid
subunits
b pleated sheet
a helix
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Tertiary Structure
Hydrophobic
interactions and
van der Waals
interactions
Polypeptide
backbone
Disulfide bridge
Ionic bond
Hydrogen
bond
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Quaternary Structure
b Chains
a ChainsHemoglobin
Iron
Heme
CollagenPolypeptide chain
Polypeptidechain
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72
Interactions that Contribute to a Protein’s Shape
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Sickle-Cell Disease: A Simple Change in
Primary Structure
Red blood
cell shapeNormal cells are
full of individual
hemoglobin
molecules, each
carrying oxygen.
10 µm 10 µm
Red blood
cell shape
Fibers of abnormal
hemoglobin deform
cell into sickle
shape.
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Sickle Cell Anemia
Primary
structure
Secondary
and tertiary
structures
1 2 3
Normal hemoglobin
Val His Leu
4
Thr
5
Pro
6
Glu Glu
7Primary
structure
Secondary
and tertiary
structures
1 2 3
Sickle-cell hemoglobin
Val His Leu
4
Thr
5
Pro
6
Val Glu
7
Quaternary
structure
Normal
hemoglobin
(top view)
a
b
b
b
b
a
a
a
Function Molecules do
not associate
with one
another; each
carries oxygen.
Quaternary
structure
Sickle-cell
hemoglobin
Function Molecules
interact with
one another to
crystallize into
a fiber; capacity
to carry oxygen
is greatly reduced.
Exposed
hydrophobic
regionb subunit b subunit
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Conformation
Denaturation
Renaturation
Denatured proteinNormal protein
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Nucleic Acids
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The Roles of Nucleic Acids
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NUCLEUS
DNA
CYTOPLASM
mRNA
mRNA
Ribosome
Amino
acids
Synthesis of
mRNA in the nucleus
Movement of
mRNA into cytoplasm
via nuclear pore
Synthesis
of protein
PolypeptideNOTE TAKING SHEET ONLY
The Structure of Nucleic Acids
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5 end
3 end
Nucleoside
Nitrogenous
base
Phosphate
group
Nucleotide
Polynucleotide, or
nucleic acid
Pentose
sugar
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Phosphate group
Sugar
Nitrogenous base
N
N
O
4’
5’
1’
3’ 2’
28
7 6
39 4
5
P CH2
O
–O
O–
OH R
OH in RNA
H in DNA
O
N
NH2
N1
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Nucleotide MonomersNitrogenous bases
Pyrimidines
Purines
Pentose sugars
Cytosine
C
Thymine (in DNA)
T
Uracil (in RNA)
U
Adenine
A
Guanine
G
Deoxyribose (in DNA)
Nucleoside components
Ribose (in RNA)
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Nitrogenous bases
Adenine
Guanine
CC
NN
N
C
H
N
C
CH
O
H
Cytosine (both DNA and RNA)
Thymine (DNA only)
Uracil (RNA only)
HCC
NC
H
N
C
NH2
N
N
CHOCC
NC
H
N
CH
H
OCC
NC
H
N
C
O
HH3C
H
OCC
NC
H
N
C
O
HH
H
P U R I N E S
P Y R I M I D I N E S
NH2
NH2
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Nucleotide Polymers
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The DNA Double Helix
Sugar-phosphate
backbone
3 end5 end
Base pair (joined by
hydrogen bonding)
Old strands
Nucleotide
about to be
added to a
new strand
5 end
New strands
3 end
5 end3 end
5 end
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ATP
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