Chapter

Outline

Structures of Galactose and Fructose

Ga actose has
Galactose
as the
t e same
sa e structure
st uctu e as glucose
g ucose except
e cept the
t e
configuration at carbon four is reversed as shown here.

Chapter
Outline

Structures of Galactose and Fructose

Galactose is an aldohexose like glucose, and like glucose
it also exists in the - and -cyclic pyranose forms.

Chapter
Outline

Structures of Galactose and Fructose

Fructose is a ketohexose and like glucose it also exists in
the open-chain and cyclic forms as shown here. Notice
that fructose is a furanose (a five-membered ring). The
five-membered ring results because of the position of
the keto group in the open chain form.

Chapter
Outline

Pentoses
D-Ribose
Ribose and its derivative D-

2-deoxyribose are the most

important
p
ppentoses because
they are found in the nucleic
acids RNA and DNA.
The 2-deoxy in D-2deoxyribose means an
oxygen is omitted from the
D-ribose molecule at carbon
#2.

Chapter
Outline

Disaccharides
Disaccharides are carbohydrates consisting of two
monosaccharide units.
The two monosaccharides are connected by a glycosidic
linkage as shown here for the disaccharide lactose .

Chapter
Outline

Disaccharides
Sucrose and lactose are important disaccharides found in
the free state in nature.
Sucrose is known as table sugar while lactose is known as
milk sugar. Both undergo hydrolysis in the presence of
an acid
id or the
h enzymes sucrase or lactase,
l
respectively.
i l

Chapter
Outline

Disaccharides
Maltose is not found in the free state but is the product
when a polysaccharide is degraded during the sprouting
of grain.
Maltose undergoes hydrolysis in the presence of acid or
maltase
lt
to
t produce
d
two
t molecules
l l off glucose.
l

Chapter
Outline

Structures and Properties of Disaccharides

Maltose is derived from two glucose molecules by the
elimination of a molecule of water between the OH
group on carbon 1 of one glucose unit and the OH
group of carbon 4 on the other glucose unit.
This is
Thi
i an -1,4-glycosidic
14 l
idi linkage
li k
since
i
the
th glucose
l
units
it
have the -configuration and are joined at carbons 1 and
4.
The structure of maltose is on the followingg slide . . .

Chapter
Outline

Structures and Properties of Disaccharides

Chapter
Outline

Structures and Properties of Disaccharides

Lactose consists of a
-D-galactopyranose
galactopyranose unit linked to
an -D-glucopyranose unit.
These are joined by a -1,4-glycosidic linkage from
carbon 1 on galactose to carbon 4 on glucose.
There are two ways that the -glycosidic linkage in
lactose can be drawn (bent or stacked) . . .

Chapter
Outline

Structures and Properties of Disaccharides

Stacked structure

Bent structure

Chapter
Outline

Polysaccharides Derived from Glucose

There are three types of naturally occurring
polysaccharides. They are cellulose, glycogen, and starch
that are of major importance.

98

Chapter
Outline

Polysaccharides Derived from Glucose

Starch, glycogen, and cellulose all yield D-glucose
glucose
when hydrolyzed.

Chapter
Outline

Polysaccharides Derived from Glucose

Starch is a polysaccharide found in plants composed of
amylose and amylopectin.
Amylose is a large molecule consisting of unbranched
chains composed of about 25-1300 -D-glucose units
j i d by
joined
b -1,4-glycosidic
14 l
idi linkages.
li k
Amylopectin is a large molecule with branched chains
composed of -1,4-glycosidic linkages in the main chain
and -1,6-glycosidic
, gy
linkages
g at branch ppoints.

Chapter
Outline

Polysaccharides Derived from Glucose

The unbranched structure of amylose.

Chapter
Outline

Polysaccharides Derived from Glucose

The branched structure of amylopectin.

102

Chapter
Outline

Polysaccharides Derived from Glucose

An important reaction during digestion is the hydrolysis
of starchy foods as shown below.

Starch is not soluble in cold water due to its large size and
will form a colloidal dispersion in hot water.
Starch solutions form a blue
blue-black
black color in the presence of
free iodine.

Chapter
Outline

Polysaccharides Derived from Glucose

Glycogen is a carbohydrate polymer that is stored in the
liver and muscle tissues in animals. It is the energystorage carbohydrate in animals.
Glycogen
y g has a structure similar to amylopectin
y p
except
p
that it is more highly branched with the -1,6glycosidic linkages occurring more frequently along
the polymer chain.

Chapter
Outline

Polysaccharides Derived from Glucose

Cellulose, like starch and glycogen, is a glucose
glucose-based
based
polymer.
The glucose units in cellulose are join by -1,4-glycosidic
linkages instead of -1,4-glycosidic linkages.
This difference in stereochemistry at the anomeric carbon
allows for extensive hydrogen bonding in cellulose
cellulose.

Chapter
Outline

Haworth formula
Figure 27.9 Two
representations of
cellulose.
ll l
In
I the
th threeth
dimensional model note
the hydrogen bonding
that links the extended
cellulose polymers to
form cellulose fibers
fibers.
Three-dimensional model of cellulose

Chapter
Outline

Polysaccharides Derived from Glucose

Cellulose is the most abundant organic substance found in
nature and it is the chief structural component of plants
and wood.