chapter 19 tro powerpoint
TRANSCRIPT
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Roy KennedyMassachusetts Bay Community College
Wellesley Hills, MA
Introductory Chemistry, 3rd EditionNivaldo Tro
Chapter 19Biochemistry
2009, Prentice Hall
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Tro's Introductory Chemistry, Chapter 19
2
The Cell• Smallest structural unit in a living
organism.• The nucleus is the part of the cell
that controls cell function.• The outer boundary of the cell is
called the cell membrane.• The region between the nucleus and
the cell membrane is called the cytoplasm.The cytoplasm is filled with a number of
specialized structures that carry out much of the cell’s work.
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Tro's Introductory Chemistry, Chapter 19
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Carbohydrates
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Tro's Introductory Chemistry, Chapter 19
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Carbohydrates, Continued• Carbon, hydrogen, and oxygen.• Ratio of H:O = 2:1.
Same as in water.
• Contain carbonyl groups and alcohol groups.Large number of polar groups leads to high solubility in
water.Dissolve in blood stream.
• Also known as sugars, starches, cellulose, dextrins, and gums.
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5
Classification of Carbohydrates• Hydroxycarbonyls have many OHs and one C=O.• Names of monosaccharides and disaccharides all end in –ose.
• Monosaccharides cannot be broken down into simpler carbohydrates.Triose, tetrose, pentose, and hexose.Aldose contain aldehyde carbonyl.Ketose contain ketone carbonyl.
• Disaccharides are two monosaccharides linked.Lose H from one and OH from other.
• Polysaccharides are three or more monosaccharides linked into complex chains.Starch and cellulose polysaccharides of glucose.
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Tro's Introductory Chemistry, Chapter 19
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Carbohydrate Formula Source
Glucose (mono) C6H12O6 Blood, plants, fruit, honey
Fructose (mono) C6H12O6 Plants, fruit, honey
Galactose (mono) C6H12O6
Sucrose (disac) C12H22O11 Sugar cane and beets, maple
syrup, fruits and veggies
Maltose (disac) C12H22O11 Partial hydrolysis of starch
Lactose (disac) C12H22O11 Milk (5%)
Starch (poly) Potatoes, corn, grains
Cellulose (poly) Cell wall of plants
Saccharides
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Tro's Introductory Chemistry, Chapter 19
7
D-Glyceraldehyde
OH
C
C
C
C
O
HH H
H
OH
OHH
C HOH
COH H
CH2OH
CHOD-Erythrose
OH
C
C
C
C
O
HH OH
H
H
OHH
C OHH
COH H
CH2OH
CHOD-Threose
C OHH
CH2OH
CHO
HOCH2
C
C
O
H OH
H
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8
C
C
C
C
C
OOH
H
H H
H
OH
H
OH
OH H
C
C
C
CH2OH
CHO
OH
OH
OHH
H
H
D-Ribose D-Arabinose
C
C
C
C
C
OOH
H
H OH
H
OH
H
H
OH H
C
C
C
CH2OH
CHO
H
OH
OHH
H
OH
C
C
C
C
C
OOH
H
H OH
H
OH
OH
H
H H
C
C
C
CH2OH
CHO
H
H
OHH
OH
OH
D-Lyxose
C
C
C
C
C
OOH
H
H H
H
OH
OH
OH
H H
C
C
C
CH2OH
CHO
OH
H
OHH
OH
H
D-Xylose
Ald
open
tose
s
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Tro's Introductory Chemistry, Chapter 19
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Ring Structure• In aqueous solution, monosaccharides exist
mainly in the ring form.
C
C
C
C
C
OOH
H
H H
H
OH
H
OH
OH H
OH
OHOH
O
OH CH
CHCH
CHC
H2
Ribose
OH
C
C
C
C
C
CO
H
H
H
OH OHH H H
H OHOH
OH
OHOH
OH
O
OH
CH
CHCH
CH
CH
CH
2
Glucose
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Tro's Introductory Chemistry, Chapter 19
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Cyclic Monosaccharides• Oxygen attached to second last carbon
bonds to carbonyl carbon.Acetal formation.
• Convert carbonyl to OH.Transfer H from original O to carbonyl O.
• New OH group may be same side as CH2OH () or opposite side ().
• Haworth projection.
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11
Formation of Ring Structure
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Tro's Introductory Chemistry, Chapter 19
12
Glucose• A.k.a. blood sugar, grape
sugar, and dextrose.
• Aldohexose = sugar containing aldehyde group and six carbons.
• Source of energy for cells.5 to 6 grams in blood stream.Supplies energy for about 15
minutes.
C
C C
C
OC OH
HH
OH
OH
H
H
OH H
CH2OH
CH2OHC
C
C
CC
O
OH
OH
OH
OH
H
H
H
HH
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Tro's Introductory Chemistry, Chapter 19
13
Fructose• A.k.a. levulose, fruit
sugar.
• Ketohexose = sugar containing ketone group and six carbons.
• Sweetest known natural sugar.
C
C C
C
O
H
OH
OH
H
OH
CH2OHH
HOH2C
CC
CC
CH2OH
O
OH
OH
OHH H
H
HOH2C
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Tro's Introductory Chemistry, Chapter 19
Galactose
• Occurs in brain and nervous system.
• Only difference between glucose and galactose is spatial orientation of groups on C4.
Glucose
OH
OH
OH
OH
O
OH CH
CHC
HCH
CHC
H2
HOCH2
CC
CC
CO
OH H
H
H
OH
OH
OH H H
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Tro's Introductory Chemistry, Chapter 19
15
Disaccharides
• Disaccharides are two monosaccharides linked together.
• When monosaccharides react together, a molecule of water is released.
• The bond between the monosaccharide units is called a glycosidic link.
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Tro's Introductory Chemistry, Chapter 19
16
Sucrose
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Tro's Introductory Chemistry, Chapter 19
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Sucrose, Continued
• Also known as table sugar, cane sugar, beet sugar.
• Glucose + fructose = sucrose. —1:2-linkage involves
aldehyde group from glucose and ketone group from fructose. Gyclosidic link.
• Nonreducing sugar.Negative Benedict’s test.
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Tro's Introductory Chemistry, Chapter 19
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O
C
CC
C
C
CH2OH
H
OH
OH
H
OH
HH
OH C C
C
O
C
HOCH2
OH
H
OH
OH
H
OH
CH2OHC
3C
4
C5
O
C2
HOCH2
1
H
OH
OH
H
OH
CH2OH6
O
C1
C 2C 3
C4
CH
5
CH2OH6
H
OH
OH
H
O
HH
OH
Sucrose, Continued
Glucose Fructose
– 1:2 Glycosidic Linkage
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19
Lactose• Milk sugar.
• Glucose + galactose. -glycosidic linkage.
• Reducing sugar.Gives positive Benedict’s test.
O
C
CC
C
C
CH2OH
H
OH
OH
H
H
OH
H
O
C
CC
C
C
CH2OH
H
OH
OH
H
OH
HH
O
Galactose
Glucose
-1:4 glycosidic link
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Digestion and Hydrolysis• Digestion breaks polysaccharides and
disaccharides into monosaccharides.• Hydrolysis is the addition of water to break the
glycosidic link.Under acidic or basic conditions.
• Monosaccharides can pass through intestinal walls into the blood stream.
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Tro's Introductory Chemistry, Chapter 19
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Simple or Complex
• Monosaccharides and disaccharides are called simple sugars because they contain only two saccharide units.Also known as simple carbohydrates.
• Polysaccharides are called complex sugars because they are polymers of many saccharide units linked in chains.
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Tro's Introductory Chemistry, Chapter 19
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Polysaccharides—Starch and Cellulose• Both are made of glucose rings linked together in long
chains. The only difference is the way the rings are linked.Give only glucose on hydrolysis.The differences in the way the rings are linked results in the
different properties of starch and cellulose.• Starch.
Digestible, soft, and chewy. 1:4— link.
• Cellulose. Not digestible. Fibrous, plant structural material.1:4—link.
• Glycogen. Structure similar to glucose, except highly branched.Used for excess glucose storage in animal bloodstreams.
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Tro's Introductory Chemistry, Chapter 19
23
and Glycosidic Links
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Tro's Introductory Chemistry, Chapter 19
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Starch
—1:4 linkage
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25
Practice—Which of the Following Molecules Are Carbohydrates?
OOH
H
OH
HOH2C
H
CH2OH
OH
H
O
H
OH
OH
H
H
CH2OH
HOH2C
OO
HH
OH
OH
H
H
OH H
CH2OHCH2
CH
CH2
OH
OH
OH
CH2OH
C
C
C
C
HOH2C
O
H
H
H
OH
OH
OH
NH2
CH C
NH
CH C
NH
CH C
O
O
CH3 O
OH
CH
CH3CH3
CH2SH
O
CCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
C
OCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH
C
O
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
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Practice—Which of the Following Molecules Are Carbohydrates?, Continued
OOH
H
OH
HOH2C
H
CH2OH
OH
H
O
H
OH
OH
H
H
CH2OH
HOH2C
OO
HH
OH
OH
H
H
OH H
CH2OHCH2
CH
CH2
OH
OH
OH
CH2OH
C
C
C
C
HOH2C
O
H
H
H
OH
OH
OH
NH2
CH C
NH
CH C
NH
CH C
O
O
CH3 O
OH
CH
CH3CH3
CH2SH
O
CCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
C
OCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH
C
O
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
Carbohydrates have multiple OH groups and either C=O or two Os attached to the same C.
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Tro's Introductory Chemistry, Chapter 19
27
Lipids
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Tro's Introductory Chemistry, Chapter 19
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Lipids, Continued• Chemicals of the cell that are insoluble in water,
but soluble in nonpolar solvents.• Fatty acids, fats, oils, phospholipids, glycolipids,
some vitamins, steroids, and waxes.• Structural components of cell membrane.
Because they don’t dissolve in water.
• Long-term energy storage.• Insulation.
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Tro's Introductory Chemistry, Chapter 19
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Fatty Acids• Carboxylic acid (head) with a very long
hydrocarbon side chain (tail).• Saturated fatty acids contain no C=C double bonds
in the hydrocarbon side chain.• Unsaturated fatty acids have C=C double bonds.
Monounsaturated have one C=C. Polyunsaturated have more than one C=C.
CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 C
O
OH
HeadTail
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Tro's Introductory Chemistry, Chapter 19
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Fatty Acids, ContinuedStearic acid—C18H36O2 a saturated fatty acid.
CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 C
O
OHCH2CH2CH2CH2CH2CH3
Oleic acid—C18H36O2 a monounsaturated fatty acid.
CH2 CH2 CH CH CH2 CH2 CH2 CH2 CH2 CH2 CH2 C
O
OHCH2CH2CH2CH2CH2CH3
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Fatty Acids, Continued
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32
Fats and Oils: Triglycerides• Fats are solid at room
temperature; oils are liquids.• Trigylcerides are triesters of
glycerol with fatty acids. The bonds that join glycerol to the
fatty acids are called ester linkages.
Glycerol
CH2
CH2
CH2
OH
OH
OH
CH2
CH2
CH2
O
O
O
C
C
C
O
O
O
CH2
CH2
CH2
CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2
CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2
CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2
CH3
CH3
CH3
ester linkage
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33
Tristearin
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34
Practice—Which of the Following Molecules Are Triglycerides? Classify as Saturated or Unsaturated.
OOH
H
OH
HOH2C
H
CH2OH
OH
H
O
H
OH
OH
H
H
CH2OH
HOH2C
OO
HH
OH
OH
H
H
OH H
CH2OHCH2
CH
CH2
OH
OH
OH
CH2OH
C
C
C
C
HOH2C
O
H
H
H
OH
OH
OH
NH2
CH C
NH
CH C
NH
CH C
O
O
CH3 O
OH
CH
CH3CH3
CH2SH
O
CCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
C
OCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH
C
O
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
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35
Practice—Which of the Following Molecules Are Triglycerides? Classify as Saturated or Unsaturated, Continued.
OOH
H
OH
HOH2C
H
CH2OH
OH
H
O
H
OH
OH
H
H
CH2OH
HOH2C
OO
HH
OH
OH
H
H
OH H
CH2OHCH2
CH
CH2
OH
OH
OH
CH2OH
C
C
C
C
HOH2C
O
H
H
H
OH
OH
OH
NH2
CH C
NH
CH C
NH
CH C
O
O
CH3 O
OH
CH
CH3CH3
CH2SH
O
CCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
C
OCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH
C
O
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3OCH2
Saturated
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Tro's Introductory Chemistry, Chapter 19
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Triglycerides• Triglycerides differ in the length of the fatty acid
side chains and in the degree of unsaturation.Side chains range from 12 to 20 C.Most natural triglycerides have different fatty acid chains
in the triglyceride; simple triglycerides have three identical chains.
• Saturated fat = all saturated fatty acid chains.Warm-blooded animal fat.Solids.
• Unsaturated fats = some unsaturated fatty acid chains.Cold-blooded animal fat or vegetable oils.Liquids.
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Tro's Introductory Chemistry, Chapter 19
37
Tristearin: A Simple Triglyceride Found in
Lard
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Tro's Introductory Chemistry, Chapter 19
38
Triolein:A Simple Triglyceride Found in Olive Oil
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Tro's Introductory Chemistry, Chapter 19
39
Structure and Melting Point
Name MP °C
Class
Myristic acid 58 Sat., 14 C
Palmitic acid 63 Sat, 16 C
Stearic acid 71 Sat, 18 C
Oleic acid 16 1 DB, 18 C
Linoleic acid -5 2 DB, 18 C
Linolenic acid -11 3 DB, 18 C
• Larger fatty acid = higher melting point.
• Double bonds decrease the melting point.More DB = lower MP.
• Saturated = no DB.• Monounsaturated = 1 DB.• Polyunsaturated = many
DB.
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Tro's Introductory Chemistry, Chapter 19
40
Cis Fats and Trans Fats
• Naturally unsaturated fatty acids contain cis double bonds.
• Processed fats come from polyunsaturated fats that have been partially hydrogenated, resulting in trans double bonds.
• Trans fats seem to increase the risk of coronary disease.
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Tro's Introductory Chemistry, Chapter 19
41
Practice—Would the Following Triglyceride Be Most Likely Found in Lard or Vegetable Oil?
CH2
CH2
CH2
CH2
CH3
OC
CH2
CH2
CH2
CH2
CH2
CH
CH
CH2
O
CH2
CH2
CH2
CH
OC
CH2
CH2
CH2
CH2
CH2
CH
CH
CH2
O
CH
CH3CH
CH2
CH2
CH
OC
CH2
CH2
CH2
CH2
CH2
CH
CH
CH2
O
CH
CH3CH2
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Tro's Introductory Chemistry, Chapter 19
42
Practice—Would the Following Triglyceride Be Most Likely Found in Lard or Vegetable Oil?,
Continued
CH2
CH2
CH2
CH2
CH3
OC
CH2
CH2
CH2
CH2
CH2
CH
CH
CH2
O
CH2
CH2
CH2
CH
OC
CH2
CH2
CH2
CH2
CH2
CH
CH
CH2
O
CH
CH3CH
CH2
CH2
CH
OC C
H2CH2
CH
CH
CH2
O
CH
CH3CH2
Many unsaturations, vegetable oil
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Tro's Introductory Chemistry, Chapter 19
45
Soaps• Triglycerides can be broken down into fatty acid salts and
glycerol by treatment with a strong hydroxide solution. The reaction is called saponifcation.
• Fatty acid salts have a very polar “head” because it is ionic and a very non-polar “tail” because it is all C and H.Hydrophilic head and hydrophobic tail.
• This unique structure allows the fatty acid salts, called soaps, to help oily substances be attracted to water. Micelle formation.
Emulsification.
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Tro's Introductory Chemistry, Chapter 19
46
Micelle
Oily particle
Hydrophilic head
Hydrophobic tail
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Tro's Introductory Chemistry, Chapter 19
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Phospholipids• Esters of glycerol.• Glycerol attached to two fatty
acids and one phosphate group.• Phospholipids have hydrophilic
heads due to phosphate group, and hydrophobic tails from the fatty acid hydrocarbon chain.
• Part of lipid bilayer found in animal cell membranes.
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Tro's Introductory Chemistry, Chapter 19
48
Lipid Bilayer
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Tro's Introductory Chemistry, Chapter 19
49
Steroids• Characterized by four linked carbon
rings.• Mostly hydrocarbon-like.
Dissolve in animal fat.• Mostly have hormonal effects.• Serum cholesterol levels linked to
heart disease and stroke.Levels depend on diet, exercise,
emotional stress, genetics, etc.• Cholesterol synthesized in the liver
from saturated fats.
C
CC
CC
CC
C
CC
CC C
CC
C
C
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Tro's Introductory Chemistry, Chapter 19
50
Steroids, Continued
cholesterol
HO
CH3
CH3
CH3
CH3
CH3
O
CH3
CH3OHtestosterone
HO
CH3OH
estrogen-estradiol
O
CH3
CH3 O
OCH3C
progesterone
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Tro's Introductory Chemistry, Chapter 19
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Practice—Which of the Hormones on the Previous Slide Does the Synthetic Hormone Below Mimic?
CH3O
CH3
OH
C CH
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Tro's Introductory Chemistry, Chapter 19
52
Practice—Which of the Hormones on the Previous Slide Does the Synthetic Hormone Below Mimic?,
Continued
CH3O
CH3
OH
C CH
Mestranol—a synthetic estrogen.
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Tro's Introductory Chemistry, Chapter 19
53
Proteinsand
Amino Acids
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Tro's Introductory Chemistry, Chapter 19
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Proteins• Involved in practically all facets of cell function.• Polymers of amino acids.
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Tro's Introductory Chemistry, Chapter 19
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Protein Structure• Proteins are polymers of amino acids.• The structure of a protein is key to its function.• Enzymes are proteins that act as catalysts.• Most proteins are classified as either fibrous or globular.• Fibrous proteins have linear, simple structure.
Insoluble in water.Used in structural features of the cell.
• Globular proteins have complex, three-dimensional structure.Generally have polar R groups of the amino acids pointing
out, so they are somewhat soluble, but also maintain an area that is nonpolar in the interior.
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Fibrous & Globular Proteins
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Tro's Introductory Chemistry, Chapter 19
57
Amino Acids• NH2 group on carbon adjacent to COOH.
-amino acids.• About 20 amino acids found in proteins.
10 synthesized by humans, 10 “essential.”• Each amino acid has three-letter abbreviation.
Glycine = Gly.• High melting points.
Generally decompose at temperature > 200 °C.• Good solubility in water.• Less acidic than most carboxylic acids and less
basic than most amines.
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Tro's Introductory Chemistry, Chapter 19
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Basic Structure of Amino Acids
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Tro's Introductory Chemistry, Chapter 19
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Amino Acids• Main difference between amino acids is the side chain.
R group.
• Some R groups are polar, others are nonpolar.• Some polar R groups are acidic, others are basic.• Some R groups contain O, others N and others S.• Some R groups are rings, others are chains. • The differences in the R groups give the amino acids
their different properties.
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Tro's Introductory Chemistry, Chapter 19
Amino Acid Sidechains
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61
Amino Acid Sidechains, Continued
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Tro's Introductory Chemistry, Chapter 19
62
NH2
CH C
O
CH3
OH NH2
CH C
O
CH2
CH2
CH2
NH
C
NH
NH2 OH
NH2
CH
O
CH2
CO
NH2
OH
NH2
CH
O
CH2
CO
OH
OH
AlanineAla
ArginineArg
AsparagineAsn
Aspartic AcidAsp
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Tro's Introductory Chemistry, Chapter 19
63
NH2
CH C
O
CH2
SH OH
NH2
CH C
O
CH2
CH2
C
O
NH2 OH
NH2
CH2C
O
OH
NH2
CH C
O
CH2
CH2
C
O
OH OH
CysteineCys
GlutamineGln
GlycineGly
Glutamic AcidGlu
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Tro's Introductory Chemistry, Chapter 19
64
NH2
CH C
O
CH2
CN
CHCH
NH
OH
NH2
CHC
HCH2
O
CCH3
CH3
OH
NH2
CHC
H2
CH
O
CCH3
CH3
OH
NH2
CH C
O
CH2
CH2
CH2
CH2
NH2OH
HistidineHis
IsoleucineIle
LeucineLeu
LysineLys
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Tro's Introductory Chemistry, Chapter 19
65
NH
CH
CH2
CH2
CH2
C
O
OH
NH2
CHC
H2
OH
O
COH
NH2
CH C
O
CH2
CH2
S
CH3 OH
NH2
CHC
H2 O
CC
CHCH
CH
CHCH
OH
ProlinePro
SerineSer
MethionineMet
PhenylalaninePhe
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Tro's Introductory Chemistry, Chapter 19
66
CHC
H C
NH2
CH3
OH O
OHNH2
CHC
H2O
CCC
CHC
NH
CH
CH
CH
CH
OH
NH2
CHC
H2 O
CC
CHCH
C
CHCH
OH
OH
NH2
CHC
HCH3
O
C
CH3
OH
ThreonineThr
TryptophanTrp
TyrosineTyr
ValineVal
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67
Practice—Classify the R Group of Each Amino Acid as Acidic, Basic, Polar, or
Nonpolar.
NH2
CC
O
CH
2
CH2
C
O
OH
OH
H NH2
CCH
2
CH
O
CCH3
CH3
OH
H
NH2
CC
O
CH
2
CN
CHCH
NH
OH
HNH2
C
CH
2O
C
OHH
OH
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68
Practice—Classify the R Group of Each Amino Acid as Acidic, Basic, Polar, or
Nonpolar, Continued.
NH2
CC
O
CH
2
CH2
C
O
OH
OH
H NH2
CCH
2
CH
O
CCH3
CH3
OH
H
NH2
CC
O
CH
2
CN
CHCH
NH
OH
HNH2
C
CH
2O
C
OHH
OH
Acidic Nonpolar
PolarBasic
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Tro's Introductory Chemistry, Chapter 19
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Tro's Introductory Chemistry, Chapter 19
70
Primary Protein Structure• The primary structure is determined by the order of
amino acids in the polypeptide.
• Link COOH group of first to NH2 of second.Loss of water, condensation.Form an amide structure.Peptide bond.
• Linked amino acids are called peptides.Dipeptide = 2 amino acids, tripeptide = 3, etc.Polypeptides = many linked amino acids in a long chain.
• Changing one amino acid in the chain can alter the biochemical behavior of the protein.
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Tro's Introductory Chemistry, Chapter 19
71
Peptide Bond Formation
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Tro's Introductory Chemistry, Chapter 19
72
Practice—Draw the Structure of the Tripeptide Glu-Leu-His (Where Glu Is on the
C-Terminus).
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Tro's Introductory Chemistry, Chapter 19
73
Practice—Draw the Structure of the Tripeptide Glu-Leu-His (Where Glu Is on the
C-Terminus), Continued.
NH
CH
COH
CH2
CH2
CO
OH
O
NH
CH
CH2
CH
C
CH3
CH3
O
NH2CH
C
O
CH2
C
NCH
CH
NH
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Tro's Introductory Chemistry, Chapter 19
74
Primary StructureSickle-Cell Anemia
• Changing one amino acid in the protein can vastly alter the biochemical behavior.
• Sickle-cell anemia. Replace one Val amino acid with Glu on two of the four
chains.Red blood cells take on sickle shape that can damage organs.
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Tro's Introductory Chemistry, Chapter 19
75
Secondary Structure
• Short range repeating patterns found in protein chains.
• Maintained by interactions between amino acids that are near each other in the chain.
• Formed and held by H bonds between NH and C=O. -helix.
Most common. -pleated sheet.• Many proteins have sections that are -helix, other
sections are -sheets, and others are random coils.
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Tro's Introductory Chemistry, Chapter 19
76
-Helix
• Amino acid chain wrapped in a tight coil with the R groups pointing outward from the coil.
• The pitch is the distance between the coils.
• The pitch and helix diameter ensure bond angles are not strained and H bonds are as strong as possible.
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Tro's Introductory Chemistry, Chapter 19
77
-Helix, Continued
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Tro's Introductory Chemistry, Chapter 19
78
-Pleated Sheet
• Extended chain forms a zig-zag pattern.
• Chains linked together by H bonds.
• Silk.
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79
Practice—The Amino Acids Shown Are on Two Different Peptide Strands that Show -Pleated Sheet Secondary Structure. Show the
H-Bonds that Form Between Them with Dashed “Bonds.”
N
CH
C
CH2
CH2
CO
OH
O
N
CH
CH2
CH
C
CH3
CH3
O
N
CH
C
O
CH2
C
NCH
CH
NH
H H H
N
CH
C
CH2
CH2
C O
OH
O
N
CH
CH2
CH
C
CH3CH3
O
N
CH
C
O
CH2
C
NCH
CH
NH
HHH
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80
Practice—The Amino Acids Shown Are on Two Different Peptide Strands that Show -Pleated Sheet Secondary Structure. Show the
H-Bonds that Form Between Them with Dashed “Bonds,” Continued.
N
CH
C
CH2
CH2
CO
OH
O
N
CH
CH2
CH
C
CH3
CH3
O
N
CH
C
O
CH2
C
NCH
CH
NH
H H H
N
CH
C
CH2
CH2
C O
OH
O
N
CH
CH2
CH
C
CH3CH3
O
N
CH
C
O
CH2
C
NCH
CH
NH
HHH
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Tro's Introductory Chemistry, Chapter 19
81
Tertiary Structure• Large-scale bends and folds due to interactions
between R groups separated by large distances on the chains.
• Types of interactions include:H bonds.Disulfide linkages.
Between cysteine amino acids.Hydrophobic interactions.
Between large, nonpolar R groups.Salt bridges.
Between acidic and basic R groups.
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Tro's Introductory Chemistry, Chapter 19
82
Cysteine• The amino acid cysteine performs a
unique function in protein structure.• Cysteine units on remote parts of the
peptide chain can react together, forming a disulfide bond.
• The disulfide bond ties parts of the chain together, contributing to the tertiary structure.
C
C
NH2
O
OH
HCH
2SH
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Tro's Introductory Chemistry, Chapter 19
83
Interactions that Create Tertiary Structure
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Tro's Introductory Chemistry, Chapter 19
84
Tertiary Structure and Protein Type
• Fibrous proteins generally lack tertiary structure.Extend as long, straight chains with some secondary
structure.Generally are the structural proteins.
• Globular proteins fold in on themselves, forming complex shapes due to the tertiary interactions.Generally function as nonstructural proteins such as
enzymes.
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Tro's Introductory Chemistry, Chapter 19
85
Types of Proteins
• Tertiary structure determines the type of protein.• Globular:
Folds into a fairly compact, spherical shape.Water soluble.Mobile.
• Fibrous:Long coils aligned in stacks like pipes.Water insoluble.Provides strength to tissues.
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Fibrous & Globular Proteins
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Tro's Introductory Chemistry, Chapter 19
87
Quaternary Structure• Many proteins are composed of multiple amino
acid chains.• The way the chains are linked together is called
quaternary structure.• Interactions between chains are the same as in
tertiary structure.
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Tro's Introductory Chemistry, Chapter 19
88
Nucleic Acids
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Tro's Introductory Chemistry, Chapter 19
89
Nucleic Acids, Continued• Carry genetic information.• DNA molar mass = 6 to 16 million amu.• RNA molar mass = 20K to 40K amu.• Made of nucleotides.
Phosphoric acid unit.Five carbon sugar.Cyclic amine (base).
• Nucleotide joined by phosphate linkages.
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Tro's Introductory Chemistry, Chapter 19
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Nucleotide Structure• Each nucleotide has three parts: a cyclic pentose, a phosphate
group, and an organic aromatic base.• The pentoses are ribose or deoxyribose.• The pentoses are the central backbone of the nucleotide.• The pentose is attached to the organic base at C1 and to the
phosphate group at C5.
O
HH
H
H
OH
H
CH2
PO
OH
OH
O N
NO NH2
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Tro's Introductory Chemistry, Chapter 19
91
Sugars
C
C C
C
O
OH
H
OH
H
OH
HH
HOH2CC
C C
C
O
H
H
OH
H
OH
HH
HOH2C
Deoxyribose Ribose
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Tro's Introductory Chemistry, Chapter 19
92
Bases• The bases are organic amines that are aromatic.
Like benzene, except containing N in the ring.Means the rings are flat rather than puckered like the sugar rings.
• Two general structures: two of the bases are similar in structure to the organic base purine; the other two bases are similar in structure to the organic base pyrimidine.
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Tro's Introductory Chemistry, Chapter 19
93
Organic Bases
NH
CNH
CH
CHC
O
O
NH
CNH
CH
CC
O
O
CH3N
CNH
CH
CHC
NH2
O
N
CHN
C
NH2
NC
C NH
CHN
CN
C
OH
NC
C NH
CH
NH2
UracilThymineCytosine
Adenine Guanine
Purines
Pyrimidines
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Tro's Introductory Chemistry, Chapter 19
94
Bases• The structures of the base are complementary,
meaning that a purine and pyrimidine will precisely align to H-bond with each other.Adenine matches thymine or uracil.Guanine matches cytosine.
PurineBases
PyrimidineBases
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Tro's Introductory Chemistry, Chapter 19
95
DNA• Deoxyribonucleic acid.• Sugar is deoxyribose.• One of the following amine bases:
Adenine (A).Guanine (G).Cytosine (C).Thymine (T).
• Two DNA strands wound together in double helix.
• Each cell has entire DNA structure.
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Tro's Introductory Chemistry, Chapter 19
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RNA• Ribonucleic acid.• Sugar is ribose.• One of the following amine bases:
Adenine (A).Guanine (G).Cytosine (C).Uracil (U).
• Single strands wound in helix.
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Tro's Introductory Chemistry, Chapter 19
97
Nucleotide FormationO
H
H
OH
H
OH
HH
HOH2C
N
N
NH2
N
NH O
H
H
OH
HHH
HOH2C
N
N
NH2
N
N+ H2O
+
O
H
H
OH
HHH
HOH2C
N
N
NH2
N
N
+ H2OOH P OH
OH
O
+OH P O
OH
O
O
H
H
OH
HHH
N
N
NH2
N
NCH2
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Tro's Introductory Chemistry, Chapter 19
98
NCH C
CH
CH
O C
N
N
CH
OH
CH
C
CHOH
CH2
N
NH2
O
P OOH
OH
Practice—Would the Nucleotide Shown Below Be Found in DNA or RNA? Is the Base a Purine or
Pyrimidine? What Is the Name of the Base?
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Tro's Introductory Chemistry, Chapter 19
99
Practice—Would the Nucleotide Shown Below Be Found in DNA or RNA? Is the Base a Purine or
Pyrimidine? What Is the Name of the Base?, Continued
NCH C
CH
CH
O C
N
N
CH
OH
CH
C
CHOH
CH2
N
NH2
O
P OOH
OH
RiboseRNA
Adenine,a purine.
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Tro's Introductory Chemistry, Chapter 19
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Primary Structure of Nucleic Acids
• Nucleotides are linked together by attaching the phosphate group of one to the sugar of another at the O of C3.
• The attachment is called a phosphate ester bond.
• The phosphate group attaches to C3 of the sugar on the next nucleotide.
CH3
CH2
C1
O
C4
Base
H
HOH
H
CH25
OPO
O
O
CH3
CH2
C1
O
C4
Base
H
HOH
H
CH25
OPO
O
O
CH
3
CH2
C1
O
C4
Base
H
HO
H
CH25
OPO
O
O
CH3
CH2
C1
O
C4
Base
H
HOH
H
CH25
OPO
O
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Tro's Introductory Chemistry, Chapter 19
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Linking Nucleotides
O
HH
H
H
OH
H
CH2
PO
OH
OH
O N
NO NH2
O
HH
H
H
OH
H
CH2
PO
OH
OH
O N
NO NH2
+
O
HH
H
HH
CH2
PO
OH
OH
O N
NO NH2
O
HH
H
H
OH
H
CH2
O
PO OH
O N
NO NH2
+ H2O
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Tro's Introductory Chemistry, Chapter 19
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Nucleotide Chain
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Tro's Introductory Chemistry, Chapter 19
103
Practice—Draw a Linked Pair of Nucleotides Having Cytosine and Thymine as the Bases.
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Tro's Introductory Chemistry, Chapter 19
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Practice—Draw a Linked Pair of Nucleotides Having Cytosine and Thymine as the Bases,
Continued.
O
CH CH2
C C
O
O
N
CNH
C
CCH
O
O
CH3P OHOH
O
OH
CH CH2
C C
OCH2
O
N
CN
CH
CH NH2
OHH
P OHO
HH
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Tro's Introductory Chemistry, Chapter 19
105
DNA Structure
• DNA made of two strands linked together by H bonds between bases.
• Bases are complementary.A pairs with T, C
with G.
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Tro's Introductory Chemistry, Chapter 19
106
Base Pairing
N
NH
CH
O
O
CH3
HN
N
N N
NHH
H AdenineThymine• Base pairing generates
the helical structure.• In DNA, the two
strands have complementary bases.Hold strands
together.Allow replication
of strand.
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Tro's Introductory Chemistry, Chapter 19
107
Adenine–Thymine Base Pair
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Tro's Introductory Chemistry, Chapter 19
108
DNA Replication
• When the DNA is to be replicated, the region to be replicated uncoils.
• This H bond between the base pairs is broken, separating the two strands.
• With the aid of enzymes, new strands of DNA are constructed by linking the complementary nucleotides to the original strand together.
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Tro's Introductory Chemistry, Chapter 19
109
DNA Replication, Continued
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Tro's Introductory Chemistry, Chapter 19
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DNA Replication, Continued
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111
Nucleic Acid → Polypeptide• Nucleic acids code for the production of proteins.• The order of bases in the nucleic acid determines the
order of amino acids in the polypeptide.• Three nucleic acids are required to code for each amino
acid.Codon.The three nucleotide sequences that code for a particular amino
acid are the same in all living organisms.
• A gene is a set of codons that code for a single protein.
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Tro's Introductory Chemistry, Chapter 19
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Protein Synthesis• Transcription → translation.• In nucleus, DNA strand at gene separates and a
complementary copy of the gene is made in RNA.Messenger RNA = mRNA.
• The mRNA travels into the cytoplasm where it links with a ribosome.
• At the ribosome, each codon on the RNA codes for a single amino acid. They are joined together to form the polypeptide chain.
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Tro's Introductory Chemistry, Chapter 19
113
Protein Synthesis, Continued
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Tro's Introductory Chemistry, Chapter 19
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Organization of Genetic Material