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Overview:

The Molecules of Life


• All living things are made up of four classes of
large biological molecules: carbohydrates,
lipids, proteins and nucleic acids
• Within cells, small organic molecules are joined
together to form larger molecules
• Macromolecules are large molecules composed
of thousands of covalently connected atoms
• Molecular structure and function are inseparable
Macromolecules are polymers, built from monomers

• Large carbohydrates, proteins and nucleic acids,


also known as macromolecules for their huge
size, are chain-like molecules called polymers.
• A polymer is a long molecule consisting of many
similar or identical building blocks linked by
covalent bonds.
• The repeating units serve as the building blocks
of a polymer are smaller molecules called
monomers
The Synthesis and Breakdown of Polymers
• Although each class of polymer is made up of a different type of
monomer, the chemical mechanisms by which cells make polymers
and break them down are similar for all classes of large biological
molecules. In cells, these processes are supported by enzymes,
specialized macromolecules (usually proteins) that speed up chemical
reactions.
• The reaction connects a monomer to another monomer or a polymer is
a condensation reaction, a reaction in which two molecules are
covalently bonded to each other with the loss of a small molecule. If a
water molecule is lost, it is known as a dehydration reaction.
• For example, carbohydrate and protein polymers are synthesized by
dehydration reactions. Each reactant contributes part of the water
molecule that is released during the reaction: One provides a hydroxyl
group (—OH), while the other provides a hydrogen (—H). This reaction
is repeated as monomers are added to the chain one by one,
lengthening the polymer.
• When polymers are disassembled to monomers by
hydrolysis, a process is the reverse of the dehydration
reaction.
• Hydrolysis means water breakage. The bond between
monomers is broken by the addition of a water molecule,
with a hydrogen from water attaching to one monomer and
the hydroxyl group attaching to the other.
• An example of hydrolysis within our bodies is the process
of digestion. The organic material in our food is in the form
of polymers that are too large to enter our cells. Within the
digestive tract, various enzymes attack the polymers,
speeding up hydrolysis. Released monomers are then
absorbed into the bloodstream for distribution to all body
cells. Those cells can then use dehydration reactions to
assemble the monomers into new, different polymers that
can perform specific functions required by the cell
The Diversity of Polymers

• Each cell has thousands of different kinds of


macromolecules. Macromolecules vary among
cells of an organism, vary more within a
species and vary even more between species
• For example, the inherited differences between
close relatives, such as human siblings, reflect
small variations in polymers, particularly DNA
and proteins.
Carbohydrates serve as fuel and building material

• Carbohydrates include sugars and the polymers of


sugars
• The simplest carbohydrates are monosaccharides,
or single sugars
• Carbohydrate macromolecules are
polysaccharides, polymers composed of many
sugar building blocks by glycosidic bond
Sugars
• Carbohydrates composed of three elements C, H,
O in a ratio of 1: 2: 1, with molecular formulas of
CH2O

• There are 4 kinds of carbohydrates:


monosaccharide, disaccharide, oligosaccharide
and polysaccharide
• Monosaccharide includes glucose, fructose and
galactose. But glucose (C6H12O6) is the most
common monosaccharide, product of
photosynthesis process ->main source of organic
compound in plant body
• Excessive glucose is stored in the form of starch
(polysaccharide) in the chloroplast. When plants
need food, starch is converted (hydrolysed) to
monosaccharides by the plant tissue enzymes
• Monosaccharides are simple sugars made up of
three to seven carbons and they can exist as a
linear chain or as ring-shaped molecules.
Monosaccharides are classified by:

•The location of the carbonyl group (as aldose or ketose). If


the sugar has an aldehyde group, meaning that the
carbonyl C is the last one in the chain, it is known as
an aldose. If the carbonyl C is internal to the chain, so that
there are other carbons on both sides of it, it forms
a ketone group and the sugar is called a ketose.

•The number of carbons in the carbon skeleton. Sugars are


also named according to their number of carbons: some of
the most common types are trioses (three carbons),
pentoses (five carbons), and hexoses (six carbons).
• Glucose, galactose and fructose have the same
chemical formula ( C6H12O6), but they differ in the
organization of their atoms, making them isomers
of one another because of the different
arrangement of functional groups around the
asymmetric carbon.

• Galactose (which forms part of lactose, the sugar


found in milk) and fructose (found in fruit).
- Glucose and galactose
are stereoisomers, their
atoms are bonded
together in the same
order, but they have a
different organization of
atoms around one of
their asymmetric
carbons.
In the diagram, a switch
in the orientation of the
hydroxyl group, marked
in red.

- Fructose is a structural isomer of glucose and galactose, meaning


that its atoms are bonded together in a different order
• Five- and six-carbon sugars can exist either as a
linear chain or in one or more ring-shaped forms
in equilibrium
• Equilibrium favors the ring forms
• Glucose is in a six-membered ring which can
occur in two different forms. The O from the
carbonyl is converted to a hydroxyl group and is
trapped either “above” the ring (on the same side
as CH2OH group) or “below” the ring (on the
opposite side from CH2OH group). When the
hydroxyl is down, glucose is in alpha (α) form
and when it’s up, glucose is in beta (β) form.
• A disaccharide is formed when a dehydration reaction joins
two monosaccharides
• The hydroxyl group of one monosaccharide combines with the
hydrogen of another, releasing a molecule of water and
forming a covalent bond known as a glycosidic linkage (next
figure)
• Each carbon atom in a monosaccharide is given a number.
• In a maltose molecule, the 1 carbon of glucose is connected
to the 4 carbon of another glucose, this bond is called a 1,4
glycosidic linkage.
• In a sucrose molecule, the 1 carbon of glucose is connected
to the 2 carbon of fructose, this bond is called a 1,2 glycosidic
linkage.
• Common disaccharides include lactose, maltose and sucrose.
• Lactose consists of glucose and galactose, found naturally in
milk. Maltose, or malt sugar made up of two glucose
molecules. The most common disaccharide is sucrose (table
sugar), made of glucose and fructose.
6 6

5 5
4 1 4 1

3 2 3 2

6 1
5
4 1 2 5

3 2 3 4 6

The diagram shows (a) 2 glucose monomers combining via a dehydration


reaction to form maltose, (b) glucose and fructose monomers form sucrose, a
disaccharide known as table sugar. (Both the reactions release a water
molecule)
Oligosaccharides and polysaccharides

• An oligosaccharide contains a small number of


monosaccharides and has functions in cell
recognition and cell adhesion.
• Polysaccharides, the polymers of sugars, have
the function as storage and structural roles
• Polysaccharide chain can be branched or
unbranched. Starch, glycogen, cellulose, and
chitin are some major examples of
polysaccharides important in living organisms
• Starch is the stored form of sugars in plants and is
made up of a mixture of two polysaccharides, amylose
and amylopectin.
• Plants synthesize glucose using light energy in
photosynthesis, and the excess glucose is stored as
starch in different plant parts, including roots and
seeds.
• The starch in the seeds provides food for the embryo as
it germinates and can also serve as a food source for
humans and animals, who will break it down into
glucose monomers using digestive enzymes
- In starch, the glucose monomers are in the alpha form and they are
connected primarily by 1,4 glycosidic linkages
•Amylose consists entirely of unbranched chains of glucose monomers
connected by 1,4 glycosidic linkages.
•Amylopectin is a branched polysaccharide. Although most of its
monomers are connected by 1,4 glycosidic linkages, additional 1,6
glycosidic linkages occur periodically and result in branch points.
- Glucose chains in amylose and amylopectin have a helical structure

Amylose
Amylopectin
• What about us? Glycogen is the storage form of
glucose in humans and other vertebrates.
Glycogen is a polymer of glucose monomers with
highly branched polymers

• Glycogen is stored in liver and muscle cells.


Whenever blood glucose levels decrease,
glycogen is broken down via hydrolysis to release
glucose monomers that cells can absorb and use
Chloroplast Starch Mitochondria Glycogen granules

0.5 µm

1 µm

Amylose Glycogen

Amylopectin

(a) Starch: a plant polysaccharide (b) Glycogen: an animal polysaccharide


Structural Polysaccharides

• Storage function is one important role for


polysaccharides, polysaccharides are essential
for another purpose: providing structure.
• Cellulose is a major component of plant cell
walls, which are rigid structures that enclose the
cells.
• Wood and paper are made of cellulose and
cellulose consist of unbranched chains of glucose
monomers linked by 1,4 glycosidic bonds
• Cellulose is made of glucose monomers in their β form
and this gives it very different properties
• The β glycosidic linkages in cellulose can't be broken
by human digestive enzymes, so humans are not
able to digest cellulose.
In the figure, every glucose monomer in the chain is flipped over
in relation to its neighbors, leading to the long, straight, non-
helical chains of cellulose. These chains cluster together to form
parallel bundles and are held together by hydrogen bonds
between hydroxyl groups, giving cellulose its rigidity and high
tensile strength, which are important to plant cells
• Polysaccharides also play an important
structural role in animal species.
• For instance, arthropods (such as insects and
crustaceans) have a hard external skeleton,
called the exoskeleton, which protects their
softer internal body parts. This exoskeleton is
made of the macromolecule chitin, which
resembles cellulose but is made out of modified
glucose units that bear a nitrogen-containing
functional group.
• Chitin is also a major component of the cell walls
of fungi
Polysaccharide Structure Function
sugar

Starch Composed of hundreds to It is a form of energy


thousands of glucose monomers, stored in plants
with little branching.
Glycogen Composed of glucose molecules A form of energy
linked together to form very stored in animals and
strong branched chains. some fungi.

Cellulose - Cellulose molecules are made - Is the main component


up of glucose molecules linked that makes up the cell
together to form straight, walls of plants.
unbranched chains.
- In humans, cellulose
- Many cellulose molecules bond helps digest food by
together to form long, parallel stimulating intestinal
fiber bundles with a solid mucosa cells to secrete
structure. mucus and wash away
waste that sticks to the
outer intestinal wall.
Chitin Made from glucose or galactose Is a component of the
molecules that have been exoskeleton of many
attached with an amino functional species such as
group to form glucosamine or shrimp, crabs, spiders
galactosamine. and the cell walls of
many fungi.
Lipids are a diverse group of hydrophobic molecules
• Fats are little molecules, ade of three long hydrocarbon tails
attached to a little molecule called glycerol. They play essential
roles in the biology of humans and other organisms.
Composed of three main elements: C, H, O.
• Have the common characteristic of being hydrophobic but
soluble in organic solvents such as ether and acetone.
• Sources of fat for humans: fatty tissue of animals, vegetable
oils from many different types of seeds and fruits such as
peanuts and sesame

Sources of fat for humans


• The feature of lipids is having little or no affinity for
water
• Lipids are hydrophobic becausethey consist mostly
of hydrocarbon chains, which form nonpolar covalent
bonds
• The function of lipids is to store energy, provide
insulation, make up cell membranes
• The most biologically important lipids are fats,
phospholipids and steroids
• Fats are constructed from two types of smaller
molecules: glycerol and fatty acids
• Glycerol is a three-carbon alcohol with a hydroxyl
group attached to each carbon
• A fatty acid consists of a carboxyl group attached to a
long carbon skeleton
Fats and oils

A fat molecule consists of two kinds of parts: a glycerol backbone


and three fatty acid tails. Glycerol is a small organic molecule with
three hydroxyl (OH) groups, while a fatty acid consists of a long
hydrocarbon chain attached to a carboxyl group.
To make a fat molecule, the hydroxyl groups on the glycerol
backbone react with the carboxyl groups of fatty acids in a
dehydration synthesis reaction. This produces a fat molecule
with three fatty acid tails bound to the glycerol backbone via
ester linkages.
Three fatty acids
are joined to
glycerol by an
ester linkage,
creating a
triacylglycerol,
or triglyceride
Saturated and unsaturated fatty acids
• Fatty acids differ in length and in their degree of
unsaturation
• If only single bonds between neighboring carbons
in the hydrocarbon chain, a fatty acid is saturated.
When the hydrocarbon chain has a double bond,
the fatty acid is unsaturated. If there is just one
double bond in a fatty acid, it’s monounsaturated,
while if there are multiple double bonds, it’s
polyunsaturated.
• Most animal fats are saturated

• Plant fats and fish fats are usually unsaturated


Saturated fatty acid

The double bonds in


unsaturated fatty acids Cis unsaturated fatty acid
can exist in either a cis
or a trans configuration.
In the cis configuration,
the two hydrogens
associated with the bond
are on the same side,
while in a trans Trans unsaturated fatty acid
configuration, they are
on opposite sides. A cis
double bond generates a
bend in the fatty acid
• The major function of fats is energy storage

• Humans and other mammals store their fat in


adipose cells
• Adipose tissue also cushions vital organs and
insulates the body

Copyright © 2008 Pearson Education, Inc., publishing as Pearson Benjamin Cummings


Phospholipids

• What keeps the watery goo (cytosol) inside of


your cells from spilling out? Cells are
surrounded by a structure called the plasma
membrane, which serves as a barrier between
the inside of the cell and its surroundings.
• Specialized lipids called phospholipids are
major components of the plasma membrane.
They are composed of fatty acid chains
attached to a backbone of glycerol.

Copyright © 2008 Pearson Education, Inc., publishing as Pearson Benjamin Cummings


• A phospholipid is an amphipathic molecule, having a
hydrophobic part and a hydrophilic part. The fatty
acid chains are hydrophobic and do not interact with
water, whereas the phosphate-containing group is
hydrophilic and interacts with water.
• In a membrane, phospholipids are arranged into a
structure called a bilayer, with their phosphate heads
facing the water and their tails pointing towards the
inside. The organization prevents the hydrophobic
tails from contacting with the water
• If a drop of phospholipids is placed in water, it form a
sphere-shaped structure known as a micelle where
the hydrophilic phosphate heads face the outside
and the fatty acids face the interior of the structure.
Hydrophilic head

Choline

Phosphate

Glycerol
Hydrophobic tails

Fatty acids

Hydrophilic
head

Hydrophobic
tails

(a) Structural formula (b) Space-filling model (c) Phospholipid symbol


Hydrophilic WATER
head

Hydrophobic
WATER
tail
Steroids
• Steroids are another class of lipid molecules, identifiable by
their structure of four fused rings. Steroids are hydrophobic
and insoluble in water.
• Cholesterol, the main steroid, is mainly synthesized in the
liver, including the sex hormones testosterone and estradiol,
which are secreted by the gonads (testes and ovaries).
• Cholesterol also serves as the starting material for other
important molecules in the body, including vitamin D and
bile acids, which aid in the digestion and absorption of fats
from dietary sources. It’s also a key component of cell
membranes, altering their fluidity and dynamics.
• Although cholesterol is essential in animals, high levels in
the blood may contribute to cardiovascular disease

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