Chapter 19 Tro Powerpoint

Roy Kennedy
Massachusetts Bay Community College

Wellesley Hills, MA
Introductory Chemistry, 3
rd
Edition
Nivaldo Tro
Chapter 19
Biochemistry
2009, Prentice Hall
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 cells work.
Carbohydrates
19
4
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.
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.
19
6
Carbohydrate Formula Source
Glucose (mono) C
6
H
12
O
6
Blood, plants, fruit, honey
Fructose (mono) C
6
H
12
O
6
Plants, fruit, honey
Galactose (mono) C
6
H
12
O
6

Sucrose (disac) C
12
H
22
O
11
Sugar cane and beets, maple
syrup, fruits and veggies
Maltose (disac) C
12
H
22
O
11
Partial hydrolysis of starch
Lactose (disac) C
12
H
22
O
11
Milk (5%)
Starch (poly) Potatoes, corn, grains
Cellulose (poly) Cell wall of plants

Saccharides
19
7
D-Glyceraldehyde
O H
C
C
C
C
O
H H H
H
OH
O H
H
C H O H
C O H H
CH
2
OH
CHO
D-Erythrose
O H
C
C
C
C
O
H
H O H
H
H
O H
H
C OH H
C O H H
CH
2
OH
CHO
D-Threose
C OH H
CH
2
OH
CHO
HOCH
2
C
C
O
H OH
H
8
C
C
C
C
C
O
O H
H
H
H
H
O H
H
O H
OH
H
C
C
C
CH
2
OH
CHO
OH
OH
OH H
H
H
D-Ribose D-Arabinose
C
C
C
C
C
O
O H
H
H
OH
H
O H
H
H
OH
H
C
C
C
CH
2
OH
CHO
H
OH
OH H
H
O H
C
C
C
C
C
O
O H
H
H
OH
H
O H
O H
H
H
H
C
C
C
CH
2
OH
CHO
H
H
OH H
O H
O H
D-Lyxose
C
C
C
C
C
O
O H
H
H
H
H
O H
O H
O H
H
H
C
C
C
CH
2
OH
CHO
OH
H
OH H
O H
H
D-Xylose
A
l
d
o
p
e
n
t
o
s
e
s

19
9
Ring Structure
In aqueous solution, monosaccharides exist mainly
in the ring form.
C
C
C
C
C
O
O H
H
H
H
H
O H
H
O H
OH
H
OH
OH
O H
O
O H
C
H
CH
C H
C
H
C
H
2
Ribose
O H
C
C
C
C
C
C
O
H
H
H
O H
O H
H
H
H
H OH
O H
OH
OH O H
O H
O
O H
C H
CH C H
CH
C H
C
H
2
Glucose
19
10
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
CH
2
OH (b) or opposite side (a).
Haworth projection.
11
Formation of Ring Structure
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
O
C
OH
H
H
OH
O H
H
H
O H
H
CH
2
OH
CH
2
OH
C
C
C
C
C
O
O H
O H
O H
OH
H
H
H
H
H
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
CH
2
OH
H
HOH
2
C
C
C
C
C
CH
2
OH
O
O H
O H
OH
H
H
H
HOH
2
C
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
O H
O
O H
C
H
C
H
C
H
C
H
C
H
C
H
2
HOCH
2
C
C
C
C
C
O
OH H
H
H
O H
O H
OH H
H
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.

19
16
Sucrose
19
17
Sucrose, Continued
Also known as table sugar, cane
sugar, beet sugar.
Glucose + fructose = sucrose.
a1:2-linkage involves
aldehyde group from glucose
and ketone group from fructose.
Gyclosidic link.
Nonreducing sugar.
Negative Benedicts test.
19
18
O
C
C C
C
C
CH
2
OH
H
OH
OH
H
OH
H H
O H
C C
C
O
C
HOCH
2
O H
H
OH
O H
H
OH
CH
2
OH
C
3
C
4
C
5
O
C
2
HOCH
2
1
H
OH
O H
H
OH
CH
2
OH
6
O
C
1
C
2
C
3
C
4
C
H
5
CH
2
OH
6
H
OH
OH
H
O
H H
O H
Sucrose, Continued
Glucose Fructose
a 1:2 Glycosidic Linkage
19
Lactose
Milk sugar.
Glucose + galactose.
b-glycosidic linkage.
Reducing sugar.
Gives positive Benedicts test.
O
C
C C
C
C
CH
2
OH
H
OH
OH
H
H
O H
H
O
C
C C
C
C
CH
2
OH
H
OH
OH
H
OH
H H
O
Galactose
Glucose
b-1:4 glycosidic link
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.
19
21
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.
19
22
PolysaccharidesStarch 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.
1:4a link.
Cellulose.
Not digestible.
Fibrous, plant structural material.
1:4b link.
Glycogen.
Structure similar to glucose, except highly branched.
Used for excess glucose storage in animal bloodstreams.
19
23
a and b Glycosidic Links
19
24
Starch
a1:4 linkage
25
PracticeWhich of the Following Molecules
Are Carbohydrates?
O
OH
H
O H
HOH
2
C
H
CH
2
OH
O H
H
O
H
O H
OH
H
H
CH
2
OH
HOH
2
C
O
O
H
H
OH
O H
H
H
O H
H
CH
2
OH
C H
2
C H
C H
2
OH
OH
OH
CH
2
OH
C
C
C
C
HOH
2
C
O
H
H
H
OH
O H
OH
N H
2
C
H
C
N
H
C
H
C
N
H
C
H
C
O
O
CH
3
O
OH
C H
CH
3
C H
3
CH
2
SH
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
PracticeWhich of the Following Molecules
Are Carbohydrates?, Continued
O
OH
H
O H
HOH
2
C
H
CH
2
OH
O H
H
O
H
O H
OH
H
H
CH
2
OH
HOH
2
C
O
O
H
H
OH
O H
H
H
O H
H
CH
2
OH
C H
2
C H
C H
2
OH
OH
OH
CH
2
OH
C
C
C
C
HOH
2
C
O
H
H
H
OH
O H
OH
N H
2
C
H
C
N
H
C
H
C
N
H
C
H
C
O
O
CH
3
O
OH
C H
CH
3
C H
3
CH
2
SH
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
Carbohydrates
have multiple OH
groups and either
C=O or two Os
attached to the
same C.
Lipids
19
28
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 dont dissolve in water.
Long-term energy storage.
Insulation.
19
29
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.
CH
3
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
C
O
OH
Head
Tail
19
30
Fatty Acids, Continued
Stearic acidC
18
H
36
O
2
a saturated fatty acid.
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
C
O
OH CH
2
CH
2
CH
2
CH
2
CH
2
CH
3
Oleic acidC
18
H
36
O
2
a monounsaturated fatty acid.
CH
2
CH
2
CH CH CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
C
O
OH CH
2
CH
2
CH
2
CH
2
CH
2
CH
3
31
Fatty Acids, Continued
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
CH
2
CH
2
CH
2
OH
OH
OH
CH
2
CH
2
CH
2
O
O
O
C
C
C
O
O
O
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
3
CH
3
CH
3
ester linkage
33
Tristearin
34
PracticeWhich of the Following Molecules Are
Triglycerides? Classify as Saturated or Unsaturated.
O
OH
H
O H
HOH
2
C
H
CH
2
OH
O H
H
O
H
O H
OH
H
H
CH
2
OH
HOH
2
C
O
O
H
H
OH
O H
H
H
O H
H
CH
2
OH
C H
2
C H
C H
2
OH
OH
OH
CH
2
OH
C
C
C
C
HOH
2
C
O
H
H
H
OH
O H
OH
N H
2
C
H
C
N
H
C
H
C
N
H
C
H
C
O
O
CH
3
O
OH
C H
CH
3
C H
3
CH
2
SH
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
35
PracticeWhich of the Following Molecules Are Triglycerides?
Classify as Saturated or Unsaturated, Continued.
O
OH
H
O H
HOH
2
C
H
CH
2
OH
O H
H
O
H
O H
OH
H
H
CH
2
OH
HOH
2
C
O
O
H
H
OH
O H
H
H
O H
H
CH
2
OH
C H
2
C H
C H
2
OH
OH
OH
CH
2
OH
C
C
C
C
HOH
2
C
O
H
H
H
OH
O H
OH
N H
2
C
H
C
N
H
C
H
C
N
H
C
H
C
O
O
CH
3
O
OH
C H
CH
3
C H
3
CH
2
SH
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
C
O
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O C H
2
Saturated
19
36
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.
19
37
Tristearin:
A Simple Triglyceride Found in
Lard
19
38
Triolein:
A Simple Triglyceride Found in Olive Oil
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.
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.
19
41
PracticeWould the Following Triglyceride Be
Most Likely Found in Lard or Vegetable Oil?
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
C
H
C
H
2
O
C H
2
C
H
2
C
H
2
C
H
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
C
H
C
H
2
O
C
H
CH
3
C H
C
H
2
C
H
2
C
H
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
C
H
C
H
2
O
C
H
CH
3
C H
2
19
42
PracticeWould the Following Triglyceride Be
Most Likely Found in Lard or Vegetable Oil?,
Continued
C
H
2
C
H
2
C
H
2
C
H
2
CH
3
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
C
H
C
H
2
O
C H
2
C
H
2
C
H
2
C
H
O
C
C
H
2
C
H
2
C
H
2
C
H
2
C
H
2
C
H
C
H
C
H
2
O
C
H
CH
3
C H
C
H
2
C
H
2
C
H
O
C C
H
2
C
H
2
C
H
C
H
C
H
2
O
C
H
CH
3
C H
2
Many unsaturations, vegetable oil
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.
19
46
Micelle
Oily particle
Hydrophilic head
Hydrophobic tail
19
47
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.
19
48
Lipid Bilayer
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
C
C
C
C
C
C
C
C
C
C
C C
C
C
C
C
19
50
Steroids, Continued
cholesterol
HO
CH
3
CH
3
CH
3
CH
3
CH
3
O
CH
3
CH
3
OH
testosterone
HO
CH
3
OH
estrogen
b-estradiol
O
CH
3
CH
3 O
O C
H
3
C
progesterone
19
51
PracticeWhich of the Hormones on the Previous
Slide Does the Synthetic Hormone Below Mimic?
CH
3
O
CH
3
OH
C CH
19
52
PracticeWhich of the Hormones on the Previous
Slide Does the Synthetic Hormone Below Mimic?,
Continued
CH
3
O
CH
3
OH
C CH
Mestranola synthetic estrogen.
Proteins
and
Amino Acids
19
54
Proteins
Involved in practically all facets of cell function.
Polymers of amino acids.
19
55
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.
Fibrous & Globular Proteins
19
57
Amino Acids
NH
2
group on carbon adjacent to COOH.
a-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.
19
58
Basic Structure of Amino Acids
19
59
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.
19
Amino Acid Sidechains
61
Amino Acid Sidechains, Continued
19
62
N H
2
C
H
C
O
CH
3
OH
NH
2
C
H
C
O
C
H
2
C
H
2
C
H
2
N
H
C
NH
N H
2
OH
NH
2
C
H
O
C
H
2
C
O
NH
2
OH
NH
2
C
H
O
C
H
2
C
O
OH
OH
Alanine
Ala
Arginine
Arg
Asparagine
Asn
Aspartic Acid
Asp
19
63
NH
2
C
H
C
O
C
H
2
S H
OH
NH
2
C
H C
O
C
H
2
C
H
2
C
O
N H
2 OH
NH
2
C H
2
C
O
OH
NH
2
C
H C
O
C
H
2
C
H
2
C
O
O H
OH
Cysteine
Cys
Glutamine
Gln
Glycine
Gly
Glutamic Acid
Glu
19
64
NH
2
C
H
C
O
C
H
2
C
N
CH
C H
N
H
OH
NH
2
C
H
C
H
C
H
2
O
C
C H
3
CH
3
OH
NH
2
C
H
C
H
2
C
H
O
C
C H
3
CH
3
OH
NH
2
C
H C
O
C
H
2
C
H
2
C
H
2
C
H
2
N H
2
OH
Histidine
His
Isoleucine
Ile
Leucine
Leu
Lysine
Lys
19
65
NH
C
H
C
H
2
C
H
2
C H
2
C
O
OH
NH
2
C
H
C
H
2
O H
O
C
OH
NH
2
C
H
C
O
C
H
2
C
H
2
S
C H
3
OH
NH
2
C
H
C
H
2
O
C
C
CH
C
H
C H
C H
C
H
OH
Proline
Pro
Serine
Ser
Methionine
Met
Phenylalanine
Phe
19
66
C
H
C
H
C
NH
2
C H
3
OH
O
OH
NH
2
C
H
C
H
2
O
C
C
C
CH
C
N
H
C
H
C H
C
H
C
H
OH
NH
2
C
H
C
H
2
O
C
C
CH
C
H
C
C H
C
H
O H
OH
NH
2
C
H
C
H
C H
3
O
C
CH
3
OH
Threonine
Thr
Tryptophan
Trp
Tyrosine
Tyr
Valine
Val
67
PracticeClassify the R Group of Each
Amino Acid as Acidic, Basic, Polar, or
Nonpolar.
NH
2
C
C
O
C
H
2
C
H
2
C
O
O H
OH
H
NH
2
C
C
H
2
C
H
O
C
C H
3
CH
3
OH
H
NH
2
C
C
O
C
H
2
C
N
CH
C H
N
H
OH
H
NH
2
C
C
H
2
O
C
O H
H
OH
68
PracticeClassify the R Group of Each
Amino Acid as Acidic, Basic, Polar, or
Nonpolar, Continued.
NH
2
C
C
O
C
H
2
C
H
2
C
O
O H
OH
H
NH
2
C
C
H
2
C
H
O
C
C H
3
CH
3
OH
H
NH
2
C
C
O
C
H
2
C
N
CH
C H
N
H
OH
H
NH
2
C
C
H
2
O
C
O H
H
OH
Acidic
Nonpolar
Polar Basic
19
69 69
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 NH
2
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.
19
71
Peptide Bond Formation
19
72
PracticeDraw the Structure of the
Tripeptide Glu-Leu-His (Where Glu Is on the
C-Terminus).
19
73
PracticeDraw the Structure of the
Tripeptide Glu-Leu-His (Where Glu Is on the
C-Terminus), Continued.
N
H
C
H
C
O H
C H
2
CH
2
C
O
OH
O
N
H
CH
C H
2
C H
C
C H
3
CH
3
O
NH
2
CH
C
O
C H
2
C
N
CH
C
H
NH
19
74
Primary Structure
Sickle-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.
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.
a-helix.
Most common.
b-pleated sheet.
Many proteins have sections that are a-helix, other
sections are b-sheets, and others are random coils.
19
76
a-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.
19
77
a-Helix, Continued
19
78
b-Pleated Sheet
Extended chain forms a
zig-zag pattern.
Chains linked together
by H bonds.
Silk.
79
PracticeThe Amino Acids Shown Are on Two Different Peptide
Strands that Show b-Pleated Sheet Secondary Structure. Show the
H-Bonds that Form Between Them with Dashed Bonds.
N
C
H
C
C H
2
CH
2
C
O
OH
O
N
CH
C H
2
C H
C
C H
3
CH
3
O
N
CH
C
O
C H
2
C
N
CH
C
H
NH
H
H H
N
C
H
C
CH
2
C H
2
C
O
O H
O
N
C H
CH
2
CH
C
CH
3
C H
3
O
N
C H
C
O
CH
2
C
N
C H
C
H
N H
H
H H
80
PracticeThe Amino Acids Shown Are on Two Different Peptide
Strands that Show b-Pleated Sheet Secondary Structure. Show the
H-Bonds that Form Between Them with Dashed Bonds,
Continued.
N
C
H
C
C H
2
CH
2
C
O
OH
O
N
CH
C H
2
C H
C
C H
3
CH
3
O
N
CH
C
O
C H
2
C
N
CH
C
H
NH
H
H H
N
C
H
C
CH
2
C H
2
C
O
O H
O
N
C H
CH
2
CH
C
CH
3
C H
3
O
N
C H
C
O
CH
2
C
N
C H
C
H
N H
H
H H
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.
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
NH
2
O
O H
H
C
H
2
S H
19
83
Interactions that Create
Tertiary Structure
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.
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.
Fibrous & Globular Proteins
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.
Nucleic Acids
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.
19
90
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
H
H
H
H
OH
H
CH
2
P O
OH
OH
O N
N O NH
2
19
91
Sugars
C
C C
C
O
OH
H
OH
H
OH
H
H
HOH
2
C
C
C C
C
O
H
H
OH
H
OH
H
H
HOH
2
C
Deoxyribose Ribose
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.

19
93
Organic Bases
N H
C
N
H
CH
CH
C
O
O
N H
C
N
H
CH
C
C
O
O
CH
3
N
C
N
H
CH
CH
C
NH
2
O
N
C H
N
C
NH
2
N
C
C
N
H
CH
N
C
N
C
OH
N
C
C
N
H
CH
N H
2
Uracil Thymine Cytosine
Adenine Guanine
Purines
Pyrimidines
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.
Purine
Bases
Pyrimidine
Bases
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.
19
96
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.
19
97
Nucleotide Formation
O
H
H
OH
H
OH
H
H
HOH
2
C
N
N
NH
2
N
N
H
O
H
H
OH
H
H
H
HOH
2
C
N
N
NH
2
N
N
+ H
2
O
+
O
H
H
OH
H
H
H
HOH
2
C
N
N
NH
2
N
N
+
H
2
O
O H P OH
OH
O
+
O H P O
OH
O
O
H
H
OH
H
H
H
N
N
NH
2
N
N
C
H
2
19
98
N
CH
C
C
H
CH
O
C
N
N
C H
OH
C
H
C
C
H
O H
C H
2
N
NH
2
O
P O O H
OH
PracticeWould the Nucleotide Shown Below Be
Found in DNA or RNA? Is the Base a Purine or
Pyrimidine? What Is the Name of the Base?
19
99
PracticeWould 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
N
CH
C
C
H
CH
O
C
N
N
C H
OH
C
H
C
C
H
O H
C H
2
N
NH
2
O
P O O H
OH
Ribose
RNA
Adenine,
a purine.
19
100
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.
C H
3
CH
2
C
1
O
C
4
Base
H
H OH
H
C H
2
5
O P O
O
O
C H
3
CH
2
C
1
O
C
4
Base
H
H OH
H
C H
2
5
O P O
O
O
C
H
3
CH
2
C
1
O
C
4
Base
H
H
O
H
C H
2
5
O P O
O
O
C H
3
CH
2
C
1
O
C
4
Base
H
H OH
H
C H
2
5
O P O
O
19
101
Linking Nucleotides
O
H
H
H
H
OH
H
CH
2
P O
OH
OH
O N
N O NH
2
O
H
H
H
H
OH
H
CH
2
P O
OH
OH
O N
N O NH
2
+
O
H
H
H
H
H
CH
2
P O
OH
OH
O N
N O NH
2
O
H
H
H
H
OH
H
CH
2
O
P O OH
O N
N O NH
2
+ H
2
O
19
102
Nucleotide Chain
19
103
PracticeDraw a Linked Pair of Nucleotides
Having Cytosine and Thymine as the Bases.
19
104
PracticeDraw a Linked Pair of Nucleotides
Having Cytosine and Thymine as the Bases,
Continued.
O
C H C
H
2
C C
O
O
N
C
NH
C
C
C H
O
O
CH
3
P OH O H
O
O H
C H C
H
2
C C
O
C H
2
O
N
C
N
C
H
C H NH
2
O
H
H
P OH O
H H
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.
19
106
Base Pairing
N
N
H
C H
O
O
C H
3
H
N
N
N
N
NH
H
H
Adenine Thymine
Base pairing generates
the helical structure.
In DNA, the two
strands have
complementary bases.
Hold strands
together.
Allow replication of
strand.
19
107
AdenineThymine Base Pair
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.
19
109
DNA Replication, Continued
19
110
DNA Replication, Continued
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.
19
112
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.
19
113
Protein Synthesis, Continued
19
114
Organization of Genetic Material

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Massachusetts Bay Community College

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