Lesson 3 - 1A2-3 Carbohydrates I & II

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Topic 1.

Molecules, Transport and Health


Chapter 1A. Chemistry for Biologists
2. Carbohydrates 1: Monosaccharides and Disaccharides
Lesson 3, Unit 1-IAL Biology
Topic 1 Molecules, Transport and Health
Specification Reference 1.2 i and 1.2 ii, 1.3, 1.4, CP1
(i) know the difference between monosaccharides, disaccharides
and polysaccharides, including glycogen and starch (amylose and
amylopectin)
(ii) be able to relate the structures of monosaccharides,
disaccharides and polysaccharides to their roles in providing and
storing energy
β-glucose and cellulose are not required in this topic.

know how monosaccharides (glucose, fructose and galactose) join


together to form disaccharides (maltose, sucrose and lactose) and
polysaccharides (glycogen, amylose and amylopectin) through
condensation reactions forming glycosidic bonds, and how these
can be split through hydrolysis reactions
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
The nutrients you need
Life on Earth evolved in the water, and all life still depends on water. At least 80% of
the mass of living organisms is water, and almost all the chemical reactions of life take
place in aqueous solution.
The other chemicals that make up living things (dry mass) are mostly organic
macromolecules (macronutrients) belonging to the four groups carbohydrates, lipids,
proteins, or nucleic acids. These macromolecules are polymers, made up from
specific monomers as shown in the table below. Between them these four groups
make up 93% of the dry mass of living organisms, the remaining 7% comprising small
organic molecules (like vitamins) and inorganic ions (micronutrients).
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2

Macronutrients
They form most of our diet and include mostly:
Carbohydrates – used to provide energy, e.g. glucose (monosaccharide) is used in
respiration to release ATP energy. Some of it is converted to glycogen (polysaccharide)
which is stored in liver, muscles and brain. Excess carbohydrate in the diet is converted
and stored as fat.
Lipids – stored as fat they are used mainly to produce energy when carbohydrates run
out. Gram to gram they actually release 2.5 times more energy than carbohydrates. In
some mammals, fat acts as a good insulation layer (blubber)
Proteins – By far the most diverse of all macronutrients. They have many complex
functions that range from enzymes, hormones, antibodies, channels in membranes, to
important cell components. They are digested to their monomers (amino acids) which
are absorbed to the bloodstream in the small intestine, carried to the cells which take
them up to make their own proteins. Essential amino acids need to be taken in our diet
as our cells cannot make them (mainly found in meat)
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Micronutrients
Micronutrients are so called because required by the body in very small amounts but
lack of them from the diet can cause serious conditions, sometimes too much of them
can also cause many problems. It refers to inorganic mineral salts and vitamins. They
are vital to development, disease prevention, and wellbeing. Micronutrients are not
produced in the body and must be derived from the diet.
Deficiencies in micronutrients such as iron, iodine, vitamin A, folate and zinc can have
devastating consequences. At least half of children worldwide ages 6 months to 5
years suffer from one or more micronutrient deficiency, and globally more than 2
billion people are affected.
Example of Minerals: iron is very important in haemoglobin formation and iron
deficiency is linked to anemia, iodine is linked to brain development, zinc promotes
immunity, calcium found in milk is very important in bone, teeth and nervous system,
sodium and potassium are needed in nerve signaling and muscular contractions.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
What are organic compounds
The dry mass of organisms. All the carbon containing macromolecules (lipids,
proteins, carbohydrates, nucleic acids...). Carbon atoms are unusual in that it
readily forms 4 covalent bonds with other carbons forming the backbone where
other atoms such as hydrogen, oxygen and less frequently nitrogen, phosphorus
and sulfur attach to.
Immense number of
molecules of different
sizes, shapes and type.
The variety of life
observed on Earth is due
to this.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
What are organic compounds
Many organic molecules (including
carbohydrates and proteins) are
composed of small molecules
(monomers) which combine to form
branched chains, rings and 3-
dimensional shapes known as
(polymers).
In carbohydrates the basic monomer
unit is a sugar (saccharide). A single
monomer is called monosaccharide. A
pair can be combined to form a
disaccharide. Monosaccharides can
also be combined in much larger
numbers to form polysaccharides.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Carbohydrates
Carbohydrates contain only the elements carbon, hydrogen and oxygen. The group
includes monomers, dimers and polymers, as shown in this diagram:

galactose
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Monosaccharides
Monosaccharides (from Greek monos: single, sacchar: sugar) are the most basic unit of
carbohydrates. They consist of one sugar and are usually colorless, water soluble,
crystalline solids with formula (CH2O)n , where n can be from 3-7.
Some monosaccharides have a sweet taste. Examples of monosaccharides include the
hexose sugars glucose, fructose, galactose. Common five‐carbon, or pentose sugars (where
n = 5, C5H10O5) include ribose and deoxyribose (found in nucleic acids and ATP) and
ribulose (which occurs in photosynthesis). Three‐carbon, or triose sugars (where n = 3,
C3H6O3) are also found in respiration and photosynthesis
Perhaps the best known monosaccharide is
glucose. It is a hexose (6 Carbon) sugar
C6H12O6. There are many isomers of glucose
where atoms are arranged in many different
ways (isomers are compounds with the same
molecular formula but different structural
formula galactose, fructose)
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Disaccharides
Pairs of monosaccharides can be combined to form
disaccharides
• Glucose linked to glucose forms maltose. It is
formed on digestion of starch by amylase, because
this enzyme breaks starch down into two‐glucose
units. Brewing beer starts with malt, which is a
maltose solution made from germinated barley.
• Glucose linked to fructose forms sucrose. It is
common in plants because it is less reactive than
glucose, and it is their main transport sugar. It is
the common table sugar that you put in your tea.
• Glucose linked to galactose forms lactose. It is
found only in mammalian milk, and is the main
source of energy for infant mammals.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Disaccharides
When the monosaccharides join, a molecule of water is removed and the reaction is
therefore called a condensation reaction (gives out water). The bond that is formed is
known as the glycosidic bond.
When water is added to a disaccharide under
suitable conditions, it breaks the glycosidic
bond releasing the constituent
monosaccharides. This is called hydrolysis
(addition of water that causes the breakdown
/ taking in water)
In general:
• polymerisation reactions are
condensations
• breakdown reactions are hydrolyses
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Polysaccharides
Polysaccharides are polymers formed by combining together many monosaccharide
molecules joined by glycosidic bonds and formed by condensation reactions. When
hydrolysed they break down into disaccharides or monosaccharides.
Polysaccharides are large and insoluble molecules. This feature makes them suitable
for storage (glycogen used in animals, starch used in plants) and for structural support
(cellulose gives support to plant cell walls, chitin forms the exoskeleton of insects)
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Starch
Starch is the plant storage polysaccharide. It is found in plant cells in the form of
small granules or grains. It is formed by the linking of between 200 - 100000 α
glucose molecules joined by glycosidic bonds in a series of condensation reactions
It is insoluble and forms starch granules inside many plant cells (especially seeds and
storage organs). It is well adapted for this because:
• Being insoluble means starch does not change the
water potential of cells, so does not cause the cells
to take up water by osmosis.
• Being insoluble it does not diffuse out of cells and is
not reactive.
• It is compact, because it coils or branches so a lot
can be stored in a small space.
• When hydrolysed it forms α glucose, which is easily
transported and easily used in respiration.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Starch
Starch is not a pure substance, but is a mixture of amylose and amylopectin. Both are
made of α glucose monomers linked by condensation reactions.
Amylose is poly (1-4) glucose, so is a long glucose chain that coils up/spirals into a helix
held together by hydrogen bonds.
Amylopectin is poly (1-4) glucose
with about 4% (1-6) branches. The
branching chains have many terminal
glucose units. Because it has more
ends, it can be broken more quickly
than amylose by amylase enzymes.
Both amylose and amylopectin are
broken down by the enzyme amylase
into maltose, though at different
rates.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Glycogen
Starch is never found in animal cells instead glycogen is the animal storage
polysaccharide (has shorter chains and is more highly branched). It is found mainly
in muscle and liver cells. It is similar in structure to amylopectin: poly (1-4) glucose
with 9% (1-6) branches.
Because it is so highly branched (more 1-6
glycosidic bonds), it can be broken down
to glucose for energy, very quickly. It is
broken down to α glucose by the enzyme
glycogen phosphorylase which act on the
edges of the polymer.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Cellulose
Cellulose is only found in plants, where it is the main component of cell walls. It is
poly (1-4) glucose, but with a different isomer of glucose. Starch and glycogen
contain α glucose, while cellulose contains β glucose, with a different position of the
hydroxyl group (OH group) on carbon 1. This apparently tiny difference makes a
huge difference in structure and properties. The α bond is flexible so starch
molecules can coil up, but the β bond is rigid, so cellulose molecules form
straight/unbranched chains.
In a cellulose chain alternate glucose molecules are inverted. To form glycosidic
bonds each β glucose must rotate 180o compared to its neighbor. The CH2OH group
alternates between being above and below the chain.
For this reason cellulose forms straight, unbranched chains. These run parallel to
one another, allowing H-bonds to form cross linkages between adjacent chains. The
great number of H-bonds strengthens cellulose making it valuable structural
material.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Cellulose
The cellulose molecules are grouped together to form microfibrils, which in turn are
arranged in parallel groups called fibrils.
Cellulose is found in plant cell walls and provides rigidity to the plant cell. The
cellulose cell wall prevents the cells from bursting when water enters the cell by
osmosis. It does this by exerting an inward pressure that stops any further influx of
water. Living plant cells become turgid and push against each other maintaining
stems and leaves in a turgid upright state so that they can provide the maximum
surface area for photosynthesis.
The β glycosidic bond cannot be broken by amylase, but requires a specific cellulase
enzyme. The only organisms that possess a cellulase enzyme are bacteria, so
herbivorous animals, like cows and termites whose diet is mainly cellulose, have
mutualistic bacteria in their guts so that they can digest cellulose. Carnivores and
omnivores cannot digest cellulose, and in humans it is referred to as fiber.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Biochemical Tests
We will cover several tests used to identify the main biologically-important chemical
compounds. Remember that for each test you need to add the reagent to a small sample
of the substance to test and, if this isn’t already a aqueous solution, grind it with some
water to break up the cells and release the cell contents. Many of these compounds are
insoluble, but the tests work just as well on a fine suspension.

Biochemical Test Used for identifying the presence of


Benedict’s test Reducing Sugars (all monosaccharides, most
disaccharides but not sucrose
Benedict’s test with Non-reducing sugars
acidification
Iodine test Starch
Biuret test Proteins
Emulsion test Lipids
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Practical Skills
The Benedict’s solution is a chemical reagent for testing reducing sugars. It a blue
solution that contains copper (II) ions. All monosaccharides and most disaccharides
(except sucrose) are called reducing sugars because they will reduce ions like Cu2+. Add a
few mL of Benedict’s reagent to the sample. Shake, and heat for a few minutes at 95°C in
a water bath.
The solution copper (II) ions in Benedict’s
reduce to copper (I) ions, forming a precipitate
and a colour change from blue to orange. The
colour and density of the precipitate gives an
indication of the amount of reducing sugar
present, so this test is semi-quantitative. The
original pale blue colour means no reducing
sugar, a green precipitate means relatively little
sugar; a brown or red precipitate means
progressively more sugar is present.
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Practical Skills
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Practical Skills
Sucrose is a non-reducing sugar, so there is no direct test for sucrose. However, if it is first
hydrolysed to its constituent monosaccharides (glucose and fructose), it will then give a
positive Benedict's test. So sucrose is the only sugar that will give a negative Benedict's
test before hydrolysis and a positive test afterwards. First test a sample for reducing
sugars, to see if there are any present before hydrolysis. Then, using a separate sample,
boil the test solution with dilute hydrochloric acid for a few minutes to hydrolyse the
glycosidic bond. Neutralise the solution by gently adding small amounts of solid sodium
hydrogen carbonate until it stops fizzing, then test as before for reducing sugars.

Sucrose will hydrolyse to


fructose and glucose after
the addition of HCl
Topic 1 Molecules, Transport and Health
Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
Practical Skills

Test for
non-reducing sugars
Topic 1 Molecules, Transport and Health
Practical Skills Chapter 1A Chemistry for Biologists - Carbohydrates 1 & 2
The presence of starch is detected with the iodine test. Add a few drops of
iodine/potassium iodide solution to the sample. A blue-black colour indicates the
presence of starch as a starch-polyiodide complex is formed.
HOMEWORK

Read Book and Revision Guides

Read 1A THINKING BIGGER, Trehalose: A sugar for dry


eyes. Be able to answer questions and prepare
presentation

Exam Practice Questions 1-4


Topic 1. Molecules, Transport and Health
Chapter 1A. Chemistry for Biologists
1. The Chemistry of Life
END OF Lesson 3, Unit 1-IAL Biology

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