Lecture 4: Biological Molecules

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 In this lecture…
• Macromolecules
– Monomers and polymers
• The four classes of biological molecules
– Lipids
• Saturated, unsaturated, trans fats
• Phospholipids
• Steroids
– Carbohydrates
• Monosaccharides, disaccharides, polysaccharides
– Proteins
• Amino acids
• Primary, secondary, tertiary, quarternary structure
– Nucleic acids
• Nucleotides
• DNA and RNA
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 The four classes of biological
molecules
• All living things are made up of four classes of large
biological molecules: carbohydrates, lipids, proteins,
and nucleic acids
• These are macromolecules - large molecules
composed of thousands of covalently connected
atoms
• Molecular structure dictates function “Macro”
= “large”
All four classes are organic molecules!

Not all organic molecules are part of one of the

four classes of biological molecules!

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What do macromolecules look like?

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 What do they do?
Type of macromolecule Example Function
Lipids Fat Cell membranes, energy
storage
Carbohydrates Starch, sugar Energy storage,
structure
Nucleic acids DNA, RNA Store genetic material
Proteins Trypsin Cell machinery

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• Polymer - a long molecule consisting of many
similar building blocks
• Monomer – the building block
• Three of the four classes of life’s organic molecules
are polymers
– Carbohydrates
– Proteins
– Nucleic acids

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 Polymers and monomers
(of both nonbiological type)

Monomer

Polymer

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Polymers and monomers
(of the nonbiological type)

Nylon monomer

Nylon polymer A monomer is a single

pattern repeated over
and over. It can be
composed of many
atoms

Nylon polymer

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 Kevlar

Polyethylene

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Creating and breaking down polymers
• Dehydration/condensation reaction - two
monomers bond together through the loss of a water
molecule
• Hydrolysis – two bonded monomers split apart using
a water molecule

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Figure 5.2 (a) Dehydration reaction: synthesizing a polymer

1 2 3
Short polymer Unlinked monomer

Dehydration removes
a water molecule,
forming a new bond.

1 2 3 4
Longer polymer

(b) Hydrolysis: breaking down a polymer

1 2 3 4

Hydrolysis adds
a water molecule,
breaking a bond.

1 2 3
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 Class I: Carbohydrates
• Sugars and the polymers of sugars
• Simplest carbohydrate monomers are
monosaccharides
• More complex carbohydrate polymers are called
polysaccharides
• Purpose: fuel and fuel storage, building material
– Sugar
– Cellulose

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 Examples of carbohydrates
• Sugar, starch, cellulose, glucose

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 Sugars Carbo = carbon,
Hydrate = water

• Monosaccharides have molecular formulas that are

usually multiples of CH2O
• Glucose (C6H12O6) is the most common
monosaccharide
• Monosaccharides are classified by
– The location of the carbonyl group (as aldose or
ketose)
– The number of carbons in the carbon skeleton
• 3, 5, or 6 carbons

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 Structure of carbohydrates
• Composed of carbon, hydrogen, and oxygen
• Though often drawn as linear skeletons, in
aqueous solutions many sugars form rings

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Figure 5.3
Aldoses (Aldehyde Sugars) Ketoses (Ketone Sugars)
Trioses: 3-carbon sugars (C3H6O3)

Glyceraldehyde Dihydroxyacetone

Pentoses: 5-carbon sugars (C5H10O5)

Ribose Ribulose

Hexoses: 6-carbon sugars (C6H12O6)

Glucose Galactose Fructose

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 Figure 5.4

1 6 6
2
5 5
3
4 1 4 1
4
2 2
5 3 3

(a) Linear and ring forms

6
5
4 1
3 2

(c) Chair structure

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(b) Abbreviated ring structure
 Monosaccharides
• Some common carbohydrate monomers…
– Fructose
• Fruit sugar
– Glucose
• Produced by photosynthesis, used as energy storage
– Ribose
• Important in RNA (ribonucleic acid)

Glucose

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 High fructose corn syrup
• Primary sweetener in the U.S. due to corn
subsidies and foreign sugar tariffs
• FDA says GRAS, but still health concerns on the
rise
• Normal corn syrup is all glucose
– Enzymatic processing converts glucose into fructose
• HFCS is 24% water, the rest sugar
– 55% fructose, 45% glucose HFCS used in soda
– Fructose is much sweeter than glucose

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Two forms of glucose: alpha () and beta ()

• Cis-trans isomers

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 2

Disaccharides
• Two monosaccharides bond together using a
dehydration reaction to create a disaccharide
– The bond between two monosaccharides is called a
glycosidic bond
• Examples of disaccharides:
– Sucrose
• Table sugar
– Lactose
• Sugar found in milk
– Maltose
• The enzyme amylase breaks down starch to produce maltose
• “Mashing” is a step in beer fermentation where amylase
produces maltose from the plant starch in barley
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A glycosidic bond/linkage joins a carbohydrate to another group, which may or
may not be another carbohydrate

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 Lactose intolerance

• Inability to digest the sugar in milk

• Caused by a lack of the enzyme lactase, which
hydrolyzes lactose into its monosaccharides glucose
and galactose
• Bacteria in your gut can metabolize it through
fermentation though, which produces hydrogen,
carbon dioxide, and methane
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 Sucrose intolerance is a rare metabolic disorder
characterized by the lack of ability to break down the
disaccharide sucrose

- What sort of diet would someone with sucrose intolerance have to

follow?
- What happens if someone with sucrose intolerance were to eat
something containing sugar?

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 Many
Polysaccharides
• Many monosaccharides linked together
through glycosidic bonds
• The structure and function of a polysaccharide
are determined by its sugar monomers and
the positions of glycosidic bonds
• Two types of polysaccharides: storage and
structural

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 Examples of polysaccharides
• Storage
– Starch
• Two types of plant starches: amylopectin and amylose
– Glycogen
• Branched chains of glucose found in animals

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 Storage polysaccharides
• Starch, a storage polysaccharide of plants,
consists entirely of glucose monomers joined
by glycosidic bonds
• Stores energy in the potential chemical energy
in the bonds of carbohydrates
– Plants store surplus starch as granules within
organelles as amylose and amylopectin
– Animals also store starch in the form of glycogen
in liver and muscle cells
• The simplest form of starch is amylose

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Figure 5.6 Amylopectin
Chloroplast Starch granules

Amylose
(a) Starch: 1 m
a plant polysaccharide

Mitochondria Glycogen granules

Glycogen
(b) Glycogen: 0.5 m
an animal polysaccharide BIOL 211 Spring 2012 29
 Structural polysaccharides
• The polysaccharide cellulose is a major component
of the tough wall of plant cells
– Like starch, cellulose is a polymer of glucose, but the
glycosidic linkages differ
• The difference is based on two ring forms for
glucose: alpha () and beta ()

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 Polymers with  Polymers with 
glucose are glucose are
helical straight

• In straight structures, H atoms on one strand can hydrogen

bond with OH groups on other strands
• Parallel cellulose molecules held together this way are
grouped into microfibrils, which form strong building
materials for plants

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Why is  glucose used in cellulose?

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 What is fiber?
• Enzymes that digest starch by hydrolyzing  linkages
can’t hydrolyze  linkages in cellulose
• Cellulose in human food passes through the digestive
tract as insoluble fiber
• Some microbes use enzymes to digest cellulose
• Many herbivores, from cows to termites, have
symbiotic relationships with these microbes

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 Structural polysaccharides
• Chitin is in the
exoskeleton of
arthropods and the
cell walls of many
fungi

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 What are the two main types of
polysaccharides? What are some examples of
each?

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 Class 2:
• The only class that does not form polymers
• Lipids are hydrophobic because they consist
mostly of hydrocarbons, which form nonpolar
covalent bonds
• The most biologically important lipids are fats,
phospholipids, and steroids
• Purpose: fuel storage, cell membranes

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 Examples of lipids
• Oils, fats, phospholipids, steroids

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 Fats
• Two components: glycerol and 3 fatty acids
• The major function of fats is energy storage
Glycerol is a three-
carbon alcohol with a A fatty acid consists of a
hydroxyl group attached carboxyl group attached to a
to each carbon long carbon skeleton

The hydrogen on this hydroxyl group can “pop”

off in water. Since the molecule is donating a
hydrogen, it is classified as an acid

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Synthesis of fats
In a fat, three fatty acids are
joined to glycerol by an ester
linkage

Generic ester functional group form:

=
R’ - C – O – C – R’

This creates a
triacylglycerol, AKA
triglyceride

In cooking, fats break apart into

smaller molecules that produce the
characteristic “deep fried” smell

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• Fatty acids vary in length (number of carbons)
and in the number and locations of double bonds
– Usually 4-35 carbons long
• Saturated fatty acids have the maximum number
of hydrogen atoms possible and no double bonds
– Each carbon ‘saturated’ with hydrogens
• Unsaturated fatty acids have one or more double
bonds

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Saturated fats
The straight hydrocarbon
chains “stack” very closely
together

(Think of
straight
pencils in a
box)

Because they are so

densely packed,
saturated fats tend to be
solid at room temp

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 Unsaturated Fats
• Includes polyunsaturated
and monounsaturated fats
on nutrition labels

The double bond “kinks” the

hydrocarbon chain and forces it to
bend

The hydrocarbon chains

don’t stack so easily, and
so are less dense.
Unsaturated fats tend to
be liquid at room temp

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Polyunsaturated and Monounsaturated Fats
• Monounsaturated fats have only one carbon-carbon double
bond
• Polyunsaturated fats have two more more carbon-carbon
double bonds
• Certain unsaturated fatty acids are not synthesized in the
human body, and must be supplied in the diet
• These essential fatty acids include the omega-3 fatty acids,
required for normal growth, and thought to provide
protection against cardiovascular disease

Poly = many
Mono = one
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 Saturated fat

The fatty acid tails can

freely rotate around
the glycerol head

Monounsaturated fat

Polyunsaturated fat

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 Trans fats
• Produced by artificially saturating unsaturated fats by adding
hydrogen – “hydrogenation”
– Nickel is added to unsaturated liquid oil as a catalyst
– The mix is exposed to high temperature and pressure as hydrogen gas
is pumped through
– Nickel is filtered out
• Hydrogenation also straightens the kinks in unsaturated fats,
isomerizing from cis to trans form
CH3
Cis form

Pentene
CH3
Trans form

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 Why hydrogenate fats?
• Saturated fats tend to be solid at room temp
– In baked goods, saturated fats produce a much better
“mouth feel” and texture than unsaturated fats
– Cheaper to hydrogenate the polyunsaturated fats in
vegetable oil than acquire natural saturated fats from
animal sources
• Saturated fats are more stable than unsaturated fats
– Beef has a longer shelf life than pork or chicken because it
has a larger proportion of saturated fats
• Partially hydrogenated vegetable oil: some of the
carbon-carbon double bonds are hydrogenated, but
not all

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 Why so bad for you?

Why are saturated fats so bad for you vs.

unsaturated fats? Why are trans fats
particularly unhealthy?

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 Why so bad for you?
“A group of identical and regular molecules fits together more neatly than
different and irregular molecules”

Triglycerides circulate in your blood. Saturated and trans fats

clump together much more easily in your blood vessels, forming
plaque that blocks arteries

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 Phospholipids
• Phospholipids are the major component of all
cell membranes
• Four components: glycerol, phosphate group,
choline, 2 fatty acids
• The two fatty acid tails are hydrophobic, but
the phosphate, glycerol, and choline form a
hydrophilic head
– The entirety of a fat molecule is hydrophobic

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 The smell of bruised
leaves and cucumbers
both come from
phospholipid fragments

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Phospholipids: the secrets of cell membranes

• When added to water, phospholipids self-assemble

into a bilayer, with the hydrophobic tails pointing
toward the interior

• The structure of phospholipids results in a bilayer

arrangement found in cell membranes
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 The notothenoids are a type of bony fish living in
Antarctica. The waters they inhabit range from -2C to
4C. What would you expect the composition of their
cell membranes to be like?

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Phospholipids in drug delivery
• A big problem in medicine is
how to get drugs inside cells
Outside the cell where they can then act

• Phospholipids can be coaxed to

form a hollow droplet called a
“liposome”

• Liposomes are filled with a drug

of interest

• Phospholipid liposomes merge

smoothly with the phospholipid
cell wall, depositing their
Inside the cell contents into the interior of the
cell
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 Phospholipids in food
• The smell of bruised leaves and cut cucumbers
comes from phospholipid fragments
• Eggs are an abundant source of the phospholipid
lecithin
– Eggs are used to produce stable mixtures of fats and
water
• Mayonnaise
• Custards
• Hollandaise sauce

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Eggs are an abundant source of the phospholipid
lecithin, and also a crucial ingredient in
mayonnaise, a smooth blend of fat and water.
How do eggs contribute to the smooth blending
of fat and water?

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 Steroids
• Steroids are lipids characterized by a carbon
skeleton consisting of four fused rings
• Cholesterol, an important steroid, is a
component in animal cell membranes

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 Cholesterol: not such a bad guy?
• Too much cholesterol can damage cell walls
and cause atherosclerosis
• Cholesterol stiffens animal cell membranes
– OH group interacts with polar region, cyclic rings
embed within nonpolar region
– Cholesterol draws fatty acid chains together, more
densely packing phospholipids and stiffening cell
membranes

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Cholesterol as a chemical precursor

Cholesterol

Enzymatic reactions

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 Birth control pills

If an egg has been fertilized, estrogen and progesterone levels remain high

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 Steroids in medicine
• Corticosteroids: used to treat a huge array of
diseases and symptoms
• Anabolic steroids: mimic the effect of testosterone
– Increase the rate of protein synthesis in cells
– Result in increased muscle mass and secondary sex
characteristics
– Excess testosterone converted to estradiol, which
causes gynomastia in men
– Natural testosterone synthesis is suppressed, resulting
in testicular atrophy and reduced sperm production

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Describe/draw the structure and function of the
three main types of lipids
Fats Phospholipids Steroids

Structure

Function

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 Looking back at this picture, what sorts of
carbohydrates and lipids would you expect to find in
strawberries?

Keep in mind:
- Plant cell wall composition
- Presence of lipids in seeds and cell walls
- Presence of sugars

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Questions?

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