CARBOHYDRATES

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 Objectives
Know the functions of carbohydrates.
Distinguish among monosaccharides,
disaccharides, and polysaccharides.
Describe the structure of a sugar.
Name the different forms of carbohydrate
molecules.
Relate the structure of polysaccharides to their
functions.
Compare storage polysaccharides with structural
polysaccharides.

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 Introduction
• Carbohydrates contain carbon, hydrogen, and
oxygen atoms in a ratio of approximately one
carbon to two hydrogens to one oxygen (CH2O)n
where the n refers to the number of “carbon
hydrate” groups. The value of n can vary from 3,
for the smallest sugar, to well over a thousand for
some of the large polymers.
• The term carbohydrate, meaning “hydrate
(water) of carbon,” refl ects the 2:1 ratio of
hydrogen to oxygen, the same ratio found in
water (H2O).

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• They are molecules with a carbonyl (C=O) and
several hydroxyl (-OH) functional groups, along with
several to many carbon–hydrogen (C-H) bonds.
• The presence of a carbonyl group along with
multiple hydroxyl groups provides sugars with an
array of reactive and hydrophilic functional groups.
• Carbohydrates are either aldehyde (aldoses) or
ketone (ketoses) in nature and they all contain
several hydroxyl (OH) groups.
• Aldoses (with a terminal carbonyl group) are more
easily oxidised than ketoses (with a non-terminal
carbonyl group). Hence, aldoses act as reducing
agents.
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• Carbohydrates are divided into three main
classes:
– Monosaccharides.
– Disaccharides.
– Polysaccharides.
• Their names typically end in a suffix -ose.

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 Functions
• Energy production (immediate energy provision)
• Energy storage
• Building macromolecules
• Structural support
• Sparing protein (Protein-saving action)
• Assisting in lipid metabolism
– “fat-sparing “effect
– Prevention of development of ketosis

• Plays an important role in cellular recognition

processes
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 Monosaccharides
• Monosaccharides typically contain from three to seven
carbon atoms.
• In a monosaccharide, a hydroxyl group is bonded to
each carbon except one; that carbon is double-
bonded to an oxygen atom, forming a carbonyl group.
• If the carbonyl group is at the end of the chain, the
monosaccharide is an aldehyde; if the carbonyl group
is at any other position, the monosaccharide is a
ketone.
• The large number of polar hydroxyl groups, plus the
carbonyl group, gives a monosaccharide hydrophilic
properties.

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• By convention, the numbering of the carbon skeleton
of a sugar begins with the carbon at or nearest the
carbonyl end of the open chain (i.e., the carbons are
conventionally numbered from the more oxidized end).
• The simplest carbohydrates are the three-carbon
sugars (trioses): glyceraldehyde and
dihydroxyacetone.
• Ribose and deoxyribose are common pentoses, sugars
that contain five carbons; they are components of
nucleic acids (DNA, RNA, and related compounds).
• Glucose, fructose, galactose, and other six-carbon
sugars are called hexoses

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• It’s rare for sugars consisting of five or more
carbons to exist in the form of the linear
chains, however. In aqueous solution they
tend to form ring structures. The bond
responsible for ring formation occurs only
between the carbon containing the carbonyl
group and one of the carbons with a hydroxyl
group.

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• Many distinct monosaccharides exist because
so many aspects of their structure are
variable: aldose or ketose placement of the
carbonyl group, variation in carbon number,
different arrangements of hydroxyl groups in
space, and alternative ring forms. Each
monosaccharide has a unique structure and
function.

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Trioses

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Pentose sugars

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The Formation of a ribose furanose
ring

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The formation of the deoxyribose
furanose ring

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Hexose sugars

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 Glucose
• Glucose (C6H12O6), the most abundant
monosaccharide, is used as an energy source in
most organisms.
• During cellular respiration, cells oxidize glucose
molecules, converting the stored energy to a form
that can be readily used for cell work.
• Glucose is also used in the synthesis of other types
of compounds such as amino acids and fatty acids.

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D and L glucose

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The formation of the glucose pyranose
ring

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 Galactose
• Galactose is a water soluble monosaccharide (aldose
sugar). It is a stereoisomer of glucose. While on OH
group on C4 of glucose is below the plane, the OH
group on C4 of galactose is above the plane i.e., It
forms a pyranose ring which differs from glucose at
C4 where the OH group is above the plane in
galactose and below the plane in glucose.
• Galactose combines with glucose to form a dimer
called lactose (milk sugar) which is present in milk.
• Galactose is a powerful reducing sugar because its
open chain has an aldehyde group.
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The formation of the galactose
pyranose ring

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 Fructose
• Fructose (fruit sugar) is a water-soluble monosaccharide
found in honey, fruits, flowers, berries, and in root crops.
• The open chain of fructose is a ketone (ketose) whose
carbon 2 combines with the OH group of carbon 5 to form
a five-membered furanose ring. Like glucose, fructose is
used as a source of energy in cellular respiration.
• Fructose is a weak reducing sugar because its open chain
structure is able to isomerise into an aldose (glucose).
• Carbon 2 of fructose is asymmetric leading to the
formation of the α- and β- isomers like in glucose.
• Fructose is a structural isomer of glucose.

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The formation of the fructose furanose
ring

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The formation of the fructose furanose
ring

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 DISACCHARIDES
• A disaccharide (two sugars) contains two
monosaccharide rings joined by a glycosidic
linkage, consisting of a central oxygen
covalently bonded to two carbons, one in
each ring.
• They are formed by the condensation
(dehydration) reaction between two
monosaccharides which are joined together
through a glycosidic bond.

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• Disaccharides serve as transport molecules in plants and
provide nutrition in animals.
• They are temporary energy stores which are broken down
by hydrolysis into their different monomers which are then
used to produce energy through cellular respiration.
• The most common disaccharides are sucrose, lactose and
maltose.
• Sucrose, common table sugar, consists of a glucose unit
combined with a fructose unit.
• Lactose (the sugar present in milk) consists of one molecule
of glucose and one of galactose.
• The disaccharide maltose (malt sugar) consists of two
covalently linked α-glucose units.
• Disaccharides are crystalline, sweet to taste and readily
dissolve in water.
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 Sucrose
• Sucrose (cane sugar) is composed of glucose
and fructose which are linked through a 1,2
glycosidic bond between C1 of α-glucose and
C2 of β-fructose.
• Its molecular formula is C12H22O11

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• It is most abundant in plants where it is
translocated in large quantities through the
phloem tissue.
• Sucrose is a non reducing sugar because it is
joined through carbon 1 of glucose and
carbon 2 of fructose that contain the
aldehyde and keto groups which have the
reducing properties in the individual open
chain structures.
• In industry, it is used as a sweetener, for
baking, confectionery and as a food
preservative. MILIMO JIGSAW
The formation and breakdown of
sucrose

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 Lactose
• Lactose (milk sugar) is composed of galactose
and glucose which are linked through a β–(1, 4)
glycosidic bond between C1 of β-galactose and
C4 of either α-glucose or β-glucose.
• It has a formula of C12H22O11 and is water soluble.
• Lactose is a reducing sugar because carbon 1 of
its glucose is free and can form an open chain to
expose the aldehyde which has the reducing
properties
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The formation and breakdown of
lactose

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Lactose and sucrose

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 Maltose
• Maltose (malt sugar) is water soluble and is
composed of two glucose molecules which
are linked through an α 1→4 glycosidic
linkage.
• It is a reducing sugar because carbon 1 on one
of its glucose monomers is free and can form
an open chain to expose the aldehyde which
has the reducing properties.

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The formation and breakdown of
maltose

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 POLYSACCHARIDES
• Polysaccharides are longer polymers made up of
monosaccharides that have been joined through
dehydration reactions.
• The polysaccharides are the most abundant
carbohydrates and include starches, glycogen, and
cellulose.
• Starch, a storage polysaccharide, consists entirely of α-
glucose molecules linked in long chains.
• Cellulose, a structural polysaccharide, also consists of
glucose molecules linked in chains, but these molecules
are β-glucose.
• Because starch is built from α-glucose we call the
linkages α linkages; cellulose has β linkages.
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• Polysaccharides are used either as:
– Food and energy stores
• Starch
• Glycogen
or as
– Structural and protective materials
• Cellulose
• Chitin
• Other functions of polysaccharides include:
– Can lubricate skeletal joints and provide adhesion
between molecules
– Complex sugar chains attached to lipids and proteins
can act as signals that determine the intracellular
location or the metabolic fate of these glycoconjugates.
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• Starch and glycogen are suitable as energy storage
molecules because they:
– Are insoluble in water.
– Don’t affect the osmotic potential of the cell.
– Are highly branched and fold into compact shapes within
limited space.
– Are easily converted to disaccharides and monosaccharides
by hydrolysis (digestion).

• Cellulose and chitin are suitable as structural materials

because they:
– Are insoluble in water.
– Are made of long thread (fibres).
– Have very high tensile strength.
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 Starch
• This is the typical form of carbohydrate used for energy
storage in plants, is a polymer consisting of α-glucose
subunits. These monomers are joined by a 14
linkages, which means that carbon 1 of one glucose is
linked to carbon 4 of the next glucose in the chain.
• This is a polymer of α-glucose monomers which first
join to form maltose. The maltose units then join to
form starch.
• Starch occurs in two forms:
– Amylose
– Amylopectin

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 Amylose
• Amylose, the simpler form, is unbranched.
• It is composed of many hundreds of α-glucose molecules
linked together in long, unbranched chains.
• Each linkage occurs between the carbon 1 (C-1) of one
glucose molecule and the C-4 of another, making them α-
(1→4) linkages (contains only α-1,4-glycosidic linkages).
• The long chains of amylose tend to coil up in water, a
property that renders amylose insoluble.
• A suspension of amylose in water gives a blue-black colour
with iodine solution because the iodide complex slips into
the α-helix coil.
• Starch is about 20% - 30% amylose

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The synthesis and breakdown of
amylose (straight chain starch)

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 Amylopectin
• Amylopectin, the more common form, usually consists of
about 1000 glucose units in a branched chain.
• The branching in amylopectin occurs when glycosidic linkages
form between the C-1 carbon of a glucose monomer on one
strand and the C-6 carbon of a glucose monomer on another
strand.
• A suspension of amylopectin in water gives a red-violet
colour with iodine solution because there is little interaction
between the iodide complex and the amylopectin.
• In amylopectin, branches occur at about one out of every 30
monomers.
• It constitutes 70-80% of starch.

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The synthesis and breakdown of
amylopectin (branched starch)

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 Glycogen
• The comparable molecule to starch in animals is glycogen.
• Like amylopectin, glycogen is an insoluble polysaccharide containing
branched amylose chains.
• Glycogen has a much longer average chain length and more branches than
plant starch.
• Glycogen is a polymer of α-glucose and is nearly identical to the branched
form of starch. However, instead of an α-1,6-glycosidic linkage occurring in
about 1 out of every 30 monomers, a branch occurs in about 1 out of
every 10 glucose subunits (its branches are shorter and more frequent).
• It is water insoluble because of the numerous α(1-4) and α(1-6) bonds
between its glucose monomers and its compact structure.
• It exists in form of granules in the cytoplasm of many types of cells but is
stored mainly in the liver and muscle cells of vertebrates.
• Glycogen is hydrolysed into glucose for use in respiration when need
arises.

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 Cellulose
• Cellulose is a structural carbohydrate. Wood
is about half cellulose, and cotton is at least
90% cellulose. Plant cells are surrounded by
strong supporting cell walls consisting mainly
of cellulose.

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• Cellulose is a polymer of β-glucose monomers,
joined by β-1,4- glycosidic linkages. The geometry
of the linkage is such that each glucose monomer
in the chain is flipped in relation to the adjacent
monomer i.e., each residue is turned 180 relative
to the preceding residue. The flipped orientation is
important because:
– It generates a linear molecule, rather than the helix
seen in starch.
– It permits multiple hydrogen bonds to form between
adjacent, parallel strands of cellulose.

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• As a result, cellulose forms long, parallel strands
that are joined by hydrogen bonds. The linked
cellulose fibers are strong and give the cell
structural support.
• It is chemically similar to amylose, with one
important difference:
– The starch-hydrolyzing enzymes that occur in most
organisms cannot break the bond between two β-
glucose units (These bonds cannot be split by the
enzymes that hydrolyze the α linkages in starch)
because they only recognize α linkages.

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• Because cellulose cannot be broken down readily
by most creatures, it works well as a biological
structural material. Some microorganisms digest
cellulose to glucose.
• In fact, cellulose-digesting bacteria (symbiotic
bacteria) and protists live in the digestive systems
of cows and sheep, enabling these grass-eating
animals to obtain nourishment from cellulose.
Similarly, the digestive systems of termites contain
microorganisms that digest cellulose. These
organisms provide the necessary enzymes for
cleaving the β-(1→4) linkages, thus enabling
access to a rich source of energy.
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• Because humans, like other animals, lack
enzymes that digest cellulose, we cannot use
it as a nutrient.
• The cellulose found in whole grains and
vegetables remains fibrous and provides bulk
that helps keep our digestive tract
functioning properly. Thus, cellulose is
important in human diets as dietary fibre.
• In industry, cellulose is used to produce paper
and cotton thread. There is some research
aimed at converting cellulose into biofuels.
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 Chitin
• Chitin, the structural material found in arthropods and
many fungi, is a polymer of N-acetylglucosamine, a
substituted version of glucose.
• It is similar to cellulose, but the hydroxyl group of
carbon 2 of each glucose unit has been replaced with
an acetamido (NH(C=O) CH3) group.
• When cross-linked by proteins, it forms a tough,
resistant surface material that serves as the hard
exoskeleton of insects and crustaceans (It is the most
important component of the external skeletons of
insects and crustaceans).
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• N-acetyl glucosamine (NAG) subunits, joined by glycosidic
bonds (β-1,4-glycosidic linkages), compose chitin, a main
component of the cell walls of fungi (stiffens the cell walls of
fungi), a few types of protists and of the external skeletons
of insects, crayfish, and other arthropods.
• Chitin forms very tough structures because, as in cellulose,
the geometry of these bonds results in every other residue
being flipped in orientation.
• Its molecules interact through multiple hydrogen bonds
(The NAG subunits in chitin form hydrogen bonds between
adjacent strands).
• The result is a tough sheet that provides stiffness and
protection.
• Some chitinous structures, such as the shell of a lobster, are
further hardened by the addition of calcium carbonate
(CaCO3), an inorganic form of carbon.
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 Peptidoglycan: A Structural
Polysaccharide in Bacteria
• Most bacteria, like all plants, have cell walls. But unlike plants, in
bacteria the ability to produce cellulose is extremely rare. Instead, a
polysaccharide called peptidoglycan gives bacterial cell walls
strength and firmness.
• Peptidoglycan is the most complex of the polysaccharides discussed
thus far. It has a long backbone formed by two types of
monosaccharides that alternate with each other and are linked by
β-1,4-glycosidic linkages. In addition, a short chain of amino acids
is attached to one of the two sugar types.
• When molecules of peptidoglycan align, peptide bonds link the
amino acid chains on adjacent strands. These links serve the same
purpose as the hydrogen bonds between the parallel strands of
cellulose and chitin in the cell walls of other organisms.

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 Glycoproteins and glycolipids
• Carbohydrates may also combine with proteins to form
glycoproteins, compounds present on the outer surface of
cells other than bacteria.
• Some of these carbohydrate chains allow cells to adhere to
one another, whereas others provide protection.
• Most proteins secreted by cells are glycoproteins. These
include the major components of mucus, a protective
material secreted by the mucous membranes of the
respiratory and digestive systems.
• Carbohydrates combine with lipids to form glycolipids,
compounds on the surfaces of animal cells that allow cells to
recognize and interact with one another.
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Metabolism of Carbohydrates

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