05 Lecture
05 Lecture
05 Lecture
Chapter 5
Carbohydrates: Life’s
Sweet Molecules
Alcohols
• Alcohol is an organic compound containing the
–OH group.
• Ethanol is one of the simplest alcohols and is
prepared from the fermentation of simple sugars
in grains and fruits. Ethanol is present in beer
and liquors, and is used as an alternative fuel
blend, such as gasohol and E85 (85% ethanol
and 15% gasoline).
Alcohols
• Alcohols are classified by the number of alkyl
groups attached to the carbon atom containing
the hydroxyl group. The number of alkyl groups
impacts the reactivity of the alcohol.
• Primary (1o) alcohols have one alkyl group
attached to the alcoholic carbon.
• Secondary (2o) alcohols have two alkyl groups
attached to the alcoholic carbon.
• Tertiary (3o) alcohols have three alkyl groups
attached to the alcoholic carbon.
Alcohols
• Monosaccharides contain both primary and
secondary alcohols.
Aldehydes
• An aldehyde is an organic compound containing
the carbonyl group.
• Benzaldehyde, a compound responsible for the
aroma of almonds and cherries, is one example.
Aldehydes
• Members of this family always
contain a carbonyl group with
a hydrogen atom bonded to
one side and an alkyl or
aromatic bonded to the other.
An exception is formaldehyde
(a preservative), which has
two hydrogens bonded to the
carbonyl group.
Aldehydes
• Monosaccharides can
contain an aldehyde group
on one end of the molecule
in addition to multiple
hydroxyl groups.
Ketones
• A ketone also contains the carbonyl group, but
has an alkyl or aromatic group on both sides of
the carbonyl group.
• Acetone is the simplest ketone. It is the main
component of fingernail polish remover.
Ketones
• A wide variety of biologically important compounds
contain a ketone group.
• Pyruvate is a ketone-containing compound formed
during the breakdown of glucose.
• Butanedione, the flavor of butter, contains two ketone
groups.
Stereochemistry in Monosaccharides
Representing stereoisomers—the
Fischer projection
• Enantiomers are written as if there is a
mirror placed between the two molecules.
• Enantiomers of D- and L-glucose are:
Maltose
• Maltose is known as malt sugar.
• It is formed by the breakdown of starch.
• Malted barley, a key ingredient in beer,
contains high levels of maltose.
• During germination of barley seeds, the starch
goes through hydrolysis to form maltose. This
process is halted by drying and roasting
barley seeds prior to their germination.
• One of the anomeric carbons is free, so
maltose is a reducing sugar.
© 2011 Pearson Education, Inc. Chapter 5 64
5.5 Disaccharides, Continued
Maltose, Continued
• The glycosidic bond is α(1→4).
Lactose
• Lactose is known as milk sugar.
• It is found in milk and milk products.
• An intolerance to lactose can occur in people
who inherit or lose the ability to produce the
enzyme lactase that hydrolyzes lactose into
its monosaccharide units.
• The glycosidic bond is (1→4).
• One of the anomeric carbons is free, so
lactose is a reducing sugar.
Sucrose
• Sucrose is known as table sugar.
• It is the most abundant disaccharide found in
nature.
• Sucrose is found in sugar cane and sugar
beets.
• The glycosidic bond is (1→2).
• Both anomeric carbons of the
monosaccharides in sucrose are bonded,
therefore, sucrose is not a reducing sugar. It
will not react with Benedict’s reagent.
© 2011 Pearson Education, Inc. Chapter 5 68
5.5 Disaccharides, Continued
Glycogen
• Glycogen is a storage polysaccharide found in
animals.
• Glycogen is stored in the liver and muscles.
• Its structure is identical to amylopectin, except
that α(1→6) branching occurs about every
12 glucose units.
• When glucose is needed, glycogen is
hydrolyzed in the liver to glucose.
Structural Polysaccharides
Cellulose
• Cellulose contains glucose units bonded
(1→4).
• This glycosidic bond configuration changes the
three-dimensional shape of cellulose compared
with that of amylose.
• The chain of glucose units is straight. This
allows chains to align next to each other to form
a strong rigid structure.
© 2011 Pearson Education, Inc. Chapter 5 77
5.6 Polysaccharides, Continued
Cellulose
• Cellulose is an insoluble fiber in our diet
because we lack the enzyme cellulase to
hydrolyze the (1→4) glycosidic bond.
• Whole grains are a good source of cellulose.
• Cellulose is important in our diet because it
assists with digestive movement in the small and
large intestine.
• Some animals and insects can digest cellulose
because they contain bacteria that produce
cellulase.
© 2011 Pearson Education, Inc. Chapter 5 79
5.6 Polysaccharides, Continued
Chitin
• Chitin makes up the exoskeleton of insects and
crustaceans and cell walls of some fungi.
• It is made up of N-acetylglucosamine containing
(1→4) glycosidic bonds.
• It is structurally strong.
• Chitin is used as surgical thread that
biodegrades as a wound heals.
• It serves as a protection from water in insects.
• Chitin is also used to waterproof paper, and in
cosmetics and lotions to retain moisture.
© 2011 Pearson Education, Inc. Chapter 5 80
5.6 Polysaccharides, Continued
Heparin
5.2 Monosaccharides
5.5 Disaccharides
5.6 Polysaccharides