Carbohydrates

Outline
• 1 Classes of Carbohydrates

• 2 Functional Groups in Monosaccharides

• 3 Stereochemistry in Monosaccharides

• 4 Reactions of Monosaccharides

• 5 Disaccharides

• 6 Polysaccharides
1 Classes of Carbohydrates
• The simplest carbohydrates are
monosaccharides (mono is Greek for
―one,‖ sakkhari is Greek for ―sugar‖).
• These often sweet-tasting sugars cannot
be broken down into smaller
carbohydrates.
• The common carbohydrate glucose,
C6H12O6, is a monosaccharide.
• Monosaccharides contain C, H, and O and
have the general formula Cn(H2O)n, where
n is a whole number 3 or higher.
 Classes of Carbohydrates

• Disaccharides consist of two

monosaccharide units joined together.
• A disaccharide can be split into two
monosaccharide units. Ordinary table sugar,
sucrose, C12H22O11, is a disaccharide that
can be broken up, through hydrolysis, into
the monosaccharides glucose and fructose.
• Oligosaccharides are carbohydrates
containing 3 to 9 monosaccharide units. The
blood-typing groups known as ABO are
oligosaccharides.
Classes of Carbohydrates

• When 10 or more monosaccharide units

are joined together, the large molecules
that result are polysaccharides (poly is
Greek for ―many‖).
• The sugar units can be connected in
one continuous chain or the chain can
be branched.
• Starch, a polysaccharide in plants,
contains branched chains of glucose
that can be broken down to produce
energy.
Classes of Carbohydrates
 Classes of Carbohydrates
FIBER IN YOUR DIET
• Dietary fibers are carbohydrates that we cannot
digest with our own enzymes.
• Soluble fiber mixes with water, forming a gel-like
substance in the stomach and digestive tract.
• This gives a sense of fullness and slows sugar
and cholesterol absorption into the bloodstream.
• Some foods high in soluble fiber include oatmeal,
legumes (peas, beans, and lentils), apples,
psyllium husk, and carrots.
• Fruit pectins used in making jellies contain
soluble fiber.
 Classes of Carbohydrates
FIBER IN YOUR DIET
• Insoluble fibers do not mix with water,
although they play a critical role in the
digestive tract.
• Insoluble fiber has a laxative effect and
adds bulk to the diet, thus preventing
constipation.
• The polysaccharide cellulose is an insoluble
fiber.
• Sources include whole grains, seeds, brown
rice, cabbage, and vegetable skins.
 Functional Groups in Monosaccharides

• Carbohydrates are
considered
polyhydroxyaldehydes
or polyhydroxy
ketones because they
contain several
hydroxyl (alcohol)
groups and either an
aldehyde or ketone
group.
Functional Groups in Monosaccharides
 Functional Groups in Monosaccharides
• The ketone family of organic compounds is
structurally similar to the aldehydes.
• The difference is that ketones have an alkyl or
aromatic group on both sides of the carbonyl.
• Ketones occur in a wide variety of biologically
relevant compounds.
 Functional Groups in Monosaccharides
• A monosaccharide that contains an aldehyde
functional group is an aldose, and one that
contains a ketone functional group is a ketose.
• A monosaccharide with three carbons is a triose,
one with four carbons is a tetrose, one with five
carbons is a pentose, and one with six carbons is
a hexose.
 The Monosaccharide - Glucose
• The most abundant monosaccharide found in
nature is glucose, also called dextrose, blood
sugar, or grape sugar.
• It is found in fruits, vegetables, and corn
syrup.
• Diabetics have difficulty getting glucose from
the bloodstream into their cells so that
glycolysis can occur. This is why they must
regularly monitor their blood glucose levels.
• Glucose is also a sugar unit in sucrose (table
sugar), lactose (milk sugar), amylase,
amylopectin, glycogen, and cellulose.
 6.3 Stereochemistry
Other Monosaccharides
in Monosaccharides
- Galactose
Important Monosaccharides: Galactose
• Galactose is found combined with glucose in
the disaccharide lactose, which is present in
milk and other dairy products.
• Galactose has a single chiral center (carbon 4)
arranged opposite that of glucose.
• The body can convert galactose into glucose
with an enzyme called an epimerase.
 6.3
Other
Stereochemistry
Monosaccharides
in Monosaccharides
- Mannose
• Mannose is a monosaccharide
found most notably in
cranberries. It is not easily
absorbed by the body.
• Mannose has been shown to be
effective against urinary tract
infections (UTIs). When the
level of mannose builds up in
the bladder, bacteria will attach
themselves to the mannose in
the urine and be eliminated.
• Mannose is an epimer of
glucose.
 6.3
Other
Stereochemistry
Monosaccharides
in Monosaccharides
- Fructose
• The ketose fructose is also
referred to as fruit sugar or
levulose. It is found in fruits,
vegetables, and honey.
• In combination with glucose,
it gives us the disaccharide
sucrose (table sugar).
• Fructose is the sweetest
monosaccharide, one and a
half times sweeter than table
sugar.
• Even though it is not an
epimer of glucose, fructose
can be broken down for
energy production in the body.
 6.3 Stereochemistry
Other in Monosaccharides
Monosaccharides - Ribose
• The pentoses ribose and 2-deoxyribose
are a part of nucleic acids.
• The nucleic acids are distinguished
in their name by the monosaccharide
they contain. Ribonucleic acid (RNA)
contains the sugar ribose, and
deoxyribonucleic acid (DNA) contains the
sugar deoxyribose.
• Structurally, the only difference between
the two pentoses is the absence of an
oxygen atom on carbon 2 of deoxyribose.
• Ribose is also found in the vitamin
riboflavin and other biologically
important molecules.
 Reactions of Monosaccharides: [O] & [R]
• The carbonyl group in aldoses can also
undergo organic oxidation and reduction.

• In monosaccharides, oxidation produces

sugar acid and reduction produces sugar
alcohol.
Disaccharides

Condensation and Hydrolysis—Forming

and Breaking Glycosidic Bonds
•In a monosaccharide in ring form, the anomeric
carbon has the most reactive –OH in the
molecule (C1 in an aldose).
•When this hydroxyl reacts with a hydroxyl on
another monosaccharide, a glycosidic bond
forms.
•Glycosidic bonds join monosaccharides to each
other and connect monosaccharides to any
alcohol.
 Disaccharides: Formation of Maltose

Figure 6.10 Formation of the disaccharide maltose.

Two molecules of glucose are joined forming a
glycosidic bond. The loss of H and OH from the
glucose molecules produces a molecule of water in
this condensation reaction.
 Disaccharides – 1. Maltose
• Maltose, or malt sugar, is a disaccharide formed in
the breakdown of starch.
• Malted barley contains high levels of maltose. The
glucose in the maltose of malted barley can be
converted to alcohol by yeast.
• The glycosidic bond in maltose is a(1→4).
• Maltose is a reducing sugar.

Figure 6.12
 Disaccharides – 2. Lactose
• Lactose, or milk sugar, is found in mammalian milk.
• Intolerance to lactose occurs in people w/o lactase.
• When lactose remains undigested, intestinal bacteria
break it down, producing abdominal gas and cramping.
• Because the anomeric carbon on the glucose unit is
free (not in a glycosidic bond), lactose is a reducing
sugar.

Figure 6.13
 Disaccharides – 3. Sucrose

• Sucrose is the most abundant disaccharide in nature:

sucrose is found in sugar cane and sugar beets.

Figure 6.14
 6.6 Polysaccharides
Storage Polysaccharides: Amylose and Amylopectin
• Starch is a glucose storage polysaccharide that
accumulates in small granules in plant cells.
• Starch is a mixture of amylose and amylopectin.
– Amylose, which makes up about 20% of starch, is made
up of 250 to 4000 D-glucose units a(1→4) bonded in a
continuous chain. Long chains of amylose tend to coil.
– Amylopectin makes up about 80% of plant starch. It also
contains D-glucose units connected by a(1→4)
glycosidic bonds. About every 25 glucose units along a
linear glucose chain, a second glucose chain branches
off through an a(1→6) glycosidic bond.
• When we eat starch, our digestive system breaks
it down into glucose units for use by our bodies.
Polysaccharides
 Polysaccharides
Storage Polysaccharides: Glycogen
• Glycogen is the storage polysaccharide found in
animals. Most glycogen stores are located in the
liver and in muscles.
• Glycogen is identical in structure to amylopectin
except that a(1→6) branching occurs about every
12 glucose units.
• Glycogen is in the liver to maintain constant
glucose levels in the blood when sugars are not
being consumed.
• The large amount of branching in this molecule
allows for quick hydrolysis when glucose is
needed.
 Polysaccharides
Structural Polysaccharides: Cellulose
• We cannot digest cellulose, but it is still an
important part of our diet because it assists with
digestive movement in the small and large
intestine.
 Polysaccharides
Structural Polysaccharides: Chitin
• Like cellulose, chitin is a strong material with many
uses, one of which is a surgical thread that
biodegrades as a wound heals.
• Chitin is present in many insects’ exoskeletons and
serves to protect them from water. Because of this
property, chitin can be used to waterproof paper.
• When ground, chitin becomes a powder that holds in
moisture, and it can be added to cosmetics and
lotions.