Carbohydrates: Classification and Importance

Chapter
Outline
Carbohydrates
Green plants
turn
H2O, CO2, and
sunlight
into
carbohydrates.
Chapter
Outline
Carbohydrates: A First Class of

Biochemicals
Carbohydrates are polyhydroxy aldehydes or ketones
(aldehydes and ketones with many hydroxyl groups).
are a principal class of energy-yielding nutrients
that are in great abundance.
Act as storehouse of chemical energy (glucose,
starch, glycogen)
Are components of supportive tissues in
plants(cellulose), crustacean shells (chitin), and
connective tissues in animals (acidic
polysaccharides)
2
Chapter
Outline

Biochemicals
Essential components of nucleic acids (D-ribose and

2-deoxy-D-ribose)
Means hydrates of carbon and has an empirical
formula Cn(H2O)m
Simplest members are often referred to as
saccharides because of their sweet taste (latin:
saccharum, sugar
The simplest
carbohydrates are
glyceraldehyde and
dihydroxyacetone.
Chapter
Outline

Biochemicals
Carbohydrates are important in society because they provide:

(1) basic diets in the form of starch and sugar and
(2) clothing and shelter.
Many of the chemical properties of carbohydrates are
determined by the chemistry of the hydroxyl and carbonyl
functional groups in the molecules.
4
Chapter
Outline
Classification of Carbohydrates
The four major types of carbohydrates are:
1) Monosaccharides
2) Disaccharides
3) Oligosaccharides
4) Polysaccharides
These classifications are based on the units

(monosaccharides) in the molecules.
5
Chapter
Outline
A monosaccharide is the smallest unit of a carbohydrate
that cannot be hydrolyzed to a simpler carbohydrate
unit. It is the basic carbohydrate unit of cellular
metabolism.
Monosaccharides have the general formula CnH2nOn,
where n varies from 3 to 8.
Glucose is a monosaccharide. Monosaccharides like
glucose are important sources of cellular energy.
6
Chapter
Outline
A disaccharide yields two monosaccharideseither the
same or differentwhen hydrolyzed.
Disaccharides are often used by plants and animals to

transport monosaccharides from one cell to another.
Chapter
Outline
The monosaccharides and disaccharides generally have
names ending in ose like glucose, sucrose, and lactose.
Monosaccharides and disaccharides are water-soluble
carbohydrates, have a characteristically sweet taste, and
are often called sugars.
Chapter
Outline
An oligosaccharide contain from 3 to about 12
monosaccharide units.
A polysaccharide is a macromolecular substance that can
be hydrolyzed to yield many monosaccharide units.
Polysacch contain > 12 monosacch units, can be 100s of
sugar units
Chapter
Outline
Polysaccharides are important structural materials in
plants and animals.
These carbohydrates also serve as a storage depot for

monosaccharides which cells use for energy.
10
Chapter
Outline
Carbohydrates can also be classified by the:
a) Number of carbon atoms in the molecule
b) Functional group present in the molecule
c) Spatial orientation of the molecule
d) Optical activity of the molecule
11
Chapter
Outline
The monosaccharides shown below are classified based on
the number of carbon atoms in the molecules.
Monosaccharides commonly have three to seven carbon
atoms.
12
Chapter
Outline
2-13
Chapter
Outline
Mononosaccharides can also be classified based on
whether they have the aldehyde or ketone functional
group.
Monosaccharides with a CHO (aldehyde) group are
known as aldoses while those with a C=O (ketone)
group are known as ketoses. The ketone group is
usually on carbon #2.
14
Chapter
Outline
Figure 7.2. Examples of an aldose (A)

and a ketose (B) sugar.
Chapter
Outline
Monosaccharides can be classified based on their spatial
orientation (stereochemistry).
A monosaccharide can be classified as a D or L isomer,
depending on the spatial orientation of the H and OH
groups attached to the carbon atom adjacent to the
terminal primary alcohol group.
The D isomer is represented when the OH is written to
the right of this carbon in the Fischer projection
formula. The L isomer is represented when this OH is
16
written to the left.
Chapter
Outline
17
Chapter
Outline
The letters D and L do not refer to the direction of optical
rotation of a carbohydrate. Monosaccharides that rotate
plane-polarized light to the right are known as (+)
isomers while those that rotate light to the left are ()
isomers.
18
Chapter
Outline
The D and L forms of any specific compound are
enantiomers. D-glucose and L-glucose are enantiomers.
Notice that orientation of the hydroxyl groups on the
carbon atoms adjacent to the terminal primary alcohol
groups.
19
Chapter
Outline
Your Turn!
Write the projection formula for a D-aldopentose.
20
Chapter
Outline
Your Turn!
This is one example of a D-aldopentose. This molecule is
a D-isomer because of the orientation of the hydroxyl
group (see arrow). The molecule is an aldose because it
is an aldehyde and a pentose because it contains five
carbon atoms.
H
OH
HO
OH
CH2OH
D-configuration
21
Chapter
Outline
Your Turn!
Classify the following as D- or L-monosaccharides and as
aldoses or ketoses.
CHO
CH2OH
CH2OH
OH
OH
OH
HO
OH
HO
HO
OH
HO
OH
CH2OH
CH2OH
CH2OH
22
Chapter
Outline
Your Turn!
Classify the following as D- or L-monosaccharides and as
aldoses or ketoses.
CHO
CH2OH
CH2OH
OH
OH
OH
HO
OH
HO
HO
OH
HO
OH
CH2OH
D-aldose
CH2OH
L-ketose
CH2OH
D-ketose
23
Chapter
Outline
Importance of Carbohydrates
Carbohydrates are the most abundant organic chemical in
nature. Why are they so important in biochemistry?
They are used by essentially all cells as an energy
source.
They are easily transported between and within cells.
They provide essential structural support for both plant

and animal cells.
24
Chapter
Outline
Monosaccharides
The most important monosaccharides are pentoses and
hexoses as seen on the next slide . . .
25
Chapter
Outline
Monosaccharides
26
Chapter
Outline
Monosaccharides
Glucose is the most important of the monosaccharides. It is
an aldohexose and is found in the free state in plant and
animal tissue. Glucose is also known as dextrose, blood
sugar and grape sugar.
Glucose is a component of the disaccharides sucrose,
maltose, and lactose and is the monomer in the
polysaccharides amylose, amylopectin, cellulose, and
glycogen.
Glucose is the key sugar of the body and is carried by the
27
bloodstream to all body parts.
Chapter
Outline
Monosaccharides
Glucose:
concentration in the blood: 80-100 mL

May be given intravenously to patrients who cannot
take food by mouth.
1 tsp = 5-6g glucose supplies energy for about 15 min.
Glucose is found in the urine of those who have
diabetes milletus
Glycosuria condition in which glucose is excreted in
the urine
28
Chapter
Outline
Monosaccharides
Galactose is an aldohexose like glucose and occurs, along

with glucose, in lactose and in many oligo- and
polysaccharides.
is synthesized in the mammary glands to make the
disaccharide lactose (milk sugar).
Hals as sweet as sugar
It is also a constituent of glycolipids and glycoproteins in
many cell membranes.
Galactosemia- the inability of infants to metabolize galactose
Increase conc. In the blood causes vomiting, diarrhea,
enlargement of the liver and often mental retardation
Early diagnosis: lactose is excluded from birth.
29
Chapter
Outline
Monosaccharides
Fructose, also known as levulose, it is a ketohexose that
occurs in fruit juices, honey, and, along with glucose, is
a constituent of the disaccharide sucrose.
is the major constituent of the polysaccharide inulin, a
starchlike substance present in many plants such as
dahlia tubers, chicory roots, and Jerusalem artichokes.
is the sweetest of all the common sugars, being about
twice as sweet as glucose. This accounts for the
sweetness of high-fructose corn syrup and honey.
Metabolized directly and also directly converted to
30
glucose in the liver.
Chapter
Outline
Monosaccharides
The Fischer projections of D-glucose, D-galactose and Dfructose are shown here.
31
Chapter
Outline
Monosaccharides
The Fischer projections of the pentoses D-ribose and D-2deoxyribose are shown here.
32
Chapter
Outline
Structure of Glucose and Other Aldoses

The structures of monosaccharides are frequently drawn as
Fischer projections- a two-dimensional representation
for showing the configuration of tetrahedral
stereocenters.
These drawings have the following characteristics.
The keto or aldehyde group is placed at the top of the
projection.
Each interior carbon atom is generally shown as an
intersection point between two lines.
The H atom and OH group attached to interior
carbons are written to left or right of the projection.
33
Chapter
Outline

In 1891, Emil Fischer made the arbitrary
assignments of D- and L- to the enantiomers of
glyceraldehyde.
CHO
H
OH
CH2 OH
CHO
HO
H
CH2 OH
D-Glyceraldehyde
L-Glyceraldehyde
25
[]D
= +13.5
25
[]D
= -13.5
D-monosaccharide: the -OH on its penultimate

carbon is on the right in a Fischer projection.
L-monosaccharide: the -OH on its penultimate
carbon is on the left in a Fischer projection.
Chapter
Outline

The simplest carbohydrate is glyceraldehyde. The Fischer
projections of D-glyceraldehyde is shown here.
35
Chapter
Outline

This is the Fischer projections of L-glyceraldehyde.
36
Chapter
Outline

The enantiomers of glyceraldehyde are also known as
epimers. Epimers are stereoisomers that differ only in
the configuration at a single chiral carbon atom.
In the case of glyceraldehyde the chiral carbon atom is #2.
37
Chapter
Outline
Figure 7.4
C-2 and C-4 epimers
and an isomer of
glucose.
Chapter
Outline

Enantiomers
- A special type of isomerism is found in the pairs of structures
that are mirror images of each other. These mirror images =
enantiomers, & the 2 members of the pair are designated as D& L-sugar. Vast majority of sugars in humans are D-sugars
Figure 7.5
Enantiomers
(mirror
images) of
glucose.
Chapter
Outline

Glucose is an aldohexose with four chiral carbon atoms.
According to the 2n formula glucose should have 16
optical isomers.
Eight have the D-configuration and eight have the Lconfiguration. Remember that D- and L- isomers are
enantiomers.
The D-isomers of the aldoses (with 3-6 carbon atoms) are
shown on Figure 27.1 on the following slide . . .
40
Chapter
Outline
41
Chapter
Outline
Your Turn!
Draw the enantiomers of D-allose and D-talose using
Figure 27.1 on the previous slide.
42
Chapter
Outline
Your Turn!
CHO
CHO
The enantiomer of Dallose is L-allose.

These molecules are
mirror images.
OH
HO
OH
HO
OH
HO
OH
HO
CH2OH
D-allose
CH2OH
43
L-allose
Chapter
Outline
Your Turn!
CHO
CHO
The enantiomer of Dtalose is L-talose.

These molecules are
mirror images.
HO
OH
HO
OH
HO
OH
OH
HO
CH2OH
CH2OH
D-talose
L-talose
44
Chapter
Outline

The 16 aldohexoses have all been synthesized, but only Dglucose, D-mannose, and D-galactose appear to be of
considerable biological importance.
The laboratory conversion of one aldose into another
aldose containing one more carbon atom is known as the
KilianiFischer synthesis.
45
Chapter
Outline

The KilianiFischer synthesis involves:
the addition of HCN to form a cyanohydrin
hydrolysis of the CN group to COOH; and
reduction with sodium amalgam, Na(Hg), to form the
aldehyde.
The synthesis of two aldotetroses from an aldotriose is
shown on the following slide . . .
46
Chapter
Outline
47
Chapter
Outline
Your Turn!
Show the conversion of D-threose (a tetrose) to two Dpentoses using the KilianiFischer synthesis.
H
HO
H
O
H
OH
CH2OH
D-threose
48
Chapter
Outline
Your Turn!
COOH
CN
H
OH
HO
H
O
H
HO
H
OH
H
HO
H
OH
H
OH
O
OH
HO
OH
H
CH2OH
CH2OH
CN
COOH
CH2OH
D-xylose
OH
CH2OH
D-threose
HO
HO
HO
HO
OH
CH2OH
OH
CH2OH
HO
HO
OH
CH2OH 49
D-lyxose
Chapter
Outline
Cyclic Structure of Glucose;

The cyclic forms of D-glucose may be represented by either
Fischer projection formulas or by Haworth perspective
formulas . . .
50
Chapter
Outline
Cyclic Structure of Glucose

In the cyclic Fischer projection formulas of the D-aldoses,
the -form has the OH on the anomeric carbon written
on the right; in the -form, the OH on the anomeric
carbon is on the left.
51
Chapter
Outline
Haworth Projections
A five- or six-membered cyclic hemiacetal is represented

as a planar ring, lying roughly perpendicular to the plane
of the paper.
Groups bonded to the carbons of the ring then lie either
above or below the plane of the ring.
The new carbon stereocenter created in forming the
cyclic structure is called the anomeric carbon.
Stereoisomers that differ in configuration only at the
anomeric carbon are called anomers.
The anomeric carbon of an aldose is C-1; that of the most
common ketoses is C-2.
Chapter
Outline
Haworth Projections
beta means that the -OH on the anomeric carbon is on the
same side of the ring as the terminal -CH2OH.
alpha means that the -OH on the anomeric carbon is on
the side of the ring opposite from the terminal -CH2OH.
53
Haworth Projections
Chapter
Outline
A six-membered hemiacetal ring is called a

pyranose, and a five-membered hemiacetal ring is
called a furanose because these ring sizes
correspond to the heterocyclic compounds furan
and pyran.
Furan
Pyran
Chapter
Outline
Chair Conformations
For pyranoses, the six-membered ring is more
accurately represented as a chair conformation.
In both Haworth projections and chair
conformations, the orientations of groups on carbons
1- 5 of b-D-glucopyranose are up, down, up, down,
and up.
6
CH2 OH
O OH(b)
H5
H
4 OH
1
H
HO
H
3
2
H OH
b-D -Glucop yranose
(Haw orth p rojection)
CH2 OH
HO
HO
5
3
OH( b)
OH
b - D -Glucopyranose
(ch air con formation)
Chapter
Outline
Your Turn!
Write the abbreviated pyranose Haworth perspective
formulas and names for the two anomers of D-galactose.
CHO
H
OH
HO
HO
OH
CH2OH
D-galactose
56
Chapter
Outline
Your Turn!
Number the open-chain, draw the Haworth pyranose ring,
and add the OH groups to all the ring carbons except
the anomeric carbon..
1 CHO
H
HO
HO
H
2
3
4
5
6
CH2OH
5
O
OH
H
H
OH
6
CH2OH
5
O
OH
1
4
OH
2
3
2
OH
6
CH2OH
D-galactose
57
Chapter
Outline
Your Turn!
Add the OH groups to the anomeric carbon atoms and
name the anomers. Notice that the hydroxyl group on
the anomeric carbon is above the ring in the -isomer
and below the ring in the -isomer.
6
CH2OH
5
O
OH
1
4
OH
3
2
OH
6
CH2OH
5
O OH
OH
1
4
OH
2
3 OH
b-D-galactopyranose
6
CH2OH
5
O
OH
+
1
OH
OH
2
3 OH
58
-D-galactopyranose
4
Chapter
Outline
Mutarotation
Mutarotation: The change in specific rotation that
accompanies the equilibration of - and b-anomers in
aqueous solution.
Example: When either -D-glucose or b-D-glucose
is dissolved in water, the specific rotation of the
solution gradually changes to an equilibrium value of
+52.7, which corresponds to 64% beta and 36%
alpha forms.
HO
HO
CH2 OH
O
OH
OH
b-D -Glucopyranose
25
[] D = + 18.7
HO
HO
CH2 OH
OH
O
C
HO
H
Open-chain form
HO
HO
CH2 OH
O
HO
OH
-D -Glucopyranose
25
[] D = +112
Chapter
Outline
Mutarotation
Enzymes are able to distinguish b/w the 2

structures & use one or the other preferentially e.g.,
glycogen is synthesized from -D-glucopyranose.
2-60
Chapter
Outline
Hemiacetals and Acetals

The reactions of aldehydes (and ketones) to form
hemiacetals and acetals has already been covered.
The hemiacetal structure consists of an ether linkage and
an alcohol linkage on the same carbon atom.
61
Chapter
Outline

The acetal structure has two ether linkages on the same
carbon atom.
62
Chapter
Outline
Cyclic Structure
Aldehydes and ketones react with alcohols to form
hemiacetals
Cyclic hemiacetals form readily when the hydroxyl
and carbonyl groups are part of the same molecule
and their interaction can form a five- or sixmembered ring.
O
4
red raw to show

-OH an d -CHO
clos e to each oth er
O-H
4-Hyd roxypentanal
O
H
H
O
H
O-H
O
A cyclic hemiacetal
Chapter
Outline

The cyclic structures of monosaccharides are intramolecular
hemiacetals. Five and six -membered ring hemiacetals
are stable . . .
64
Chapter
Outline

In an aqueous solution, the ring often opens and the
hemiacetal momentarily reverts to the open chain
aldehyde. When the open chain closes, it forms either
the - or the -anomer during mutarotation as discussed
previously.
65
Chapter
Outline

Cyclic acetals are known as glycosides which are
derivatives of hemiacetals.
66
Chapter
Outline

Glycosides like the methyl isomers shown below are less
reactive than the corresponding monosaccharides.
The methyl isomers shown below will not undergo
mutarotation.
67
Chapter
Outline
Structures of Galactose and Fructose

Galactose has the same structure as glucose except the
configuration at carbon four is reversed as shown here.
68
Chapter
Outline

Galactose is an aldohexose like glucose, and like glucose
it also exists in the - and -cyclic pyranose forms.
69
Chapter
Outline

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.
70
Chapter
Outline
Pentoses
D-Ribose and its derivative
D-2-deoxyribose are the
most important pentoses

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.
71
Chapter
Outline
Pentoses
Ribulose is a ketose that is related to
ribose. It is a biological
intermediate used by cells to make
other monosaccharides.
72
Chapter
Outline
Your Turn!
Write the Haworth formula for -D-ribofuranose.
73
Chapter
Outline
Your Turn!
Write the Haworth formula for -D-ribofuranose.
1 CHO
H
H
H
2
3
4
5
OH
OH
OH
CH2OH
D-ribose
5 CH2OH
O OH
4
1
3
2
OH OH
b-D-ribofuranose
74
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 .
75
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 or the enzymes sucrase or lactase, respectively.
76
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 to produce two molecules of glucose.
77
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 an -1,4-glycosidic linkage since the glucose units
have the -configuration and are joined at carbons 1 and
4.
The structure of maltose is on the following slide . . .
78
Chapter
Outline
79
Chapter
Outline

Lactose is the principal sugar present in milk; It
makes up about 5 to 8 percent of human milk and 4
to 6 percent of cow's milk.
Lactose consists of a -D-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) . . .
80
Chapter
Outline

Stacked structure
Bent structure
81
Chapter
Outline

Sucrose is the most abundant disaccharide in the
biological world; it is obtained principally from the
juice of sugar cane and sugar beets.
Sucrose consists of an -D-glucopyranose unit and a -Dfructofuranose unit.
These monosaccharides are joined by an -1,2-glycosidic
linkage . . .
82
Chapter
Outline
Structures and
Properties of
Disaccharides
83
Chapter
Outline
Your Turn!
Draw a disaccharide formed from two -D-glucopyranose
units with an -1,4-glycosidic linkage.
CH2OH
O
OH
OH
OH
OH
-D-glucopyranose
84
Chapter
Outline
Your Turn!
Draw a disaccharide formed from two -D-glucopyranose
units with an -1,4-glycosidic linkage.
6
CH2OH
5
O
6
CH2OH
5
O
1 + 4
4
OH
OH 3
OH
2
OH
-D-glucopyranose
OH
OH 3
6
CH2OH
5
O
6
CH2OH
5
O
OH
2
OH
-D-glucopyranose
OH
OH
OH 3
2
OH
O
3
OH
2
OH
disaccharide with -glycosidic

linkage. This disaccharide is maltose.
85
Chapter
Outline
Sweeteners and Diet

Sucrose represents 40-60% of all sweeteners and is 20-30%
of the average caloric intake in the United States.
Sucrose is hydrolyzed to glucose and fructose to prevent
crystallization in certain food preparations and in these
cases it is known as invert sugar.
86
Chapter
Outline
Sweeteners and Diet

Artificial sweeteners have been developed with the intent
to balance concerns for safety, relative sweetness, and
aftertaste.
Many artificial sweeteners have a higher relative
sweetness than the common sweeteners like sucrose,
glucose or fructose as shown in Table 27.1 on the next
slide . . .
87
Chapter
Outline
88
Chapter
Outline
Sweeteners and Diet

The compounds shown below are examples of artificial
sweeteners.
89
Chapter
Outline
Redox Reactions of Monosaccharides

The redox chemistry of carbohydrates is fundamental to
life.
Glucose is the most important carbohydrate in
biochemistry. Almost all cells derive energy from the
oxidation of glucose through glycolysis, citric acid cycle,
and oxidative phosphorylation. The energy yield from
the oxidation of glucose is shown below.
90
Chapter
Outline

The aldehyde group in monosaccharides can be oxidized to
monocarboxylic acids with a mild oxidizing agent. For
example glucose is oxidized to gluconic acid in the
presence of bromine and water.
91
Chapter
Outline

Dicarboxylic acids are formed when aldohexoses are
treated with stronger oxidizing agents. For example
glucose is oxidized to glucaric acid in the presence of
nitric acid.
92
Chapter
Outline

Hexahydric alcohols (containing six OH groups) are
formed when aldohexoses are treated with reducing
agents. The reduction product is called an alditol.
Alditols are named by changing the suffix -ose to -itol.
For example glucose is reduced to glucitol (sorbitol) in the
presence of H2/Pt.
93
Chapter
Outline
Alditols
Sorbitol is found in the plant world in many berries and

in cherries, plums, pears, apples, seaweed, and algae.
It is about 60 percent as sweet as sucrose (table sugar)
and is used in the manufacture of candies and as a
sugar substitute for diabetics.
These three alditols are also common in the biological
world.
CH2 OH
H
OH
H
OH
CH2 OH
Erythritol
CH2 OH
HO
H
HO
H
H
OH
H
OH
CH2 OH
D -Mannitol
CH2 OH
H
OH
HO
H
H
OH
CH2 OH
Xylitol
Chapter
Outline

Under prescribed conditions, some sugars reduce silver
ions to free silver and copper(II) ions to copper(I) ions.
Such sugars are called reducing sugars.
A reducing sugar will have one of the following groups.
An aldehyde group (as in glyceraldehyde)
A hydroxyketone (as in fructose)
A cyclic hemiacetal group (as in glucose and maltose)
95
Chapter
Outline
Reducing sugars:
- If the oxygen on the anomeric C (the carbonyl group)
of a sugar is not attached to any other structure, that
sugar is a reducing sugar.
- A reducing sugar can react with chemical reagents
e.g., Benedicts soln & reduce the reactive
component, with the anomeric C becoming oxidized
Note: only the state of the oxygen on the anomeric C
determines if the sugar is reducing or non-reducing,
the other hydroxyl groups on the molecule are not
involved
Chapter
Outline

The Benedict, Barfoed, and Fehling tests are based on the
formation of a brick red copper(I) oxide precipitate as a
positive result while the Tollens test is based on the
formation of a silver mirror.
The Barfoed test is more sensitive in that it can distinguish
a reducing monosaccharide from a reducing
disaccharide.
The sugars are oxidized to carboxylic acids and the metal
ions are reduced . . .
97
Chapter
Outline
98
Chapter
Outline

Many clinical tests that monitor color change are
based on the oxidation reaction shown here.
99
Chapter
Outline

Sugars with the hemiacetal structure can be reduced under
alkaline conditions because the ring opens as shown
below forming an aldehyde group.
100
Chapter
Outline

Glucose, lactose, and maltose have the hemiacetal
structure and are reducing sugars, but the disaccharide
sucrose is not a reducing sugar because it does not have
the hemiacetal structure.
101
Chapter
Outline
Your Turn!
Draw the products formed when D-ribose reacts with Br2
and water?
CHO
H
OH
OH
OH
CH2OH
D-ribose
102
Chapter
Outline
Your Turn!
Draw the products formed when D-ribose reacts with Br2
and water?
CHO
COOH
OH
OH
OH
CH2OH
+ Br2 + H2O
OH
OH
OH
+ 2 HBr
CH2OH
D-ribose
Notice that the product is a carboxylic acid.
103
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.
104
Chapter
Outline

Starch, glycogen, and cellulose all yield D-glucose
when hydrolyzed.
105
Chapter
Outline

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
joined by -1,4-glycosidic linkages.
Amylopectin is a large molecule with branched chains

composed of -1,4-glycosidic linkages in the main chain
and -1,6-glycosidic linkages at branch points.
106
Chapter
Outline

The unbranched structure of amylose.
107
Chapter
Outline

The branched structure of amylopectin.
108
Chapter
Outline

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-black color in the presence of
free iodine.
109
Chapter
Outline

Glycogen is a carbohydrate polymer that is stored in the
liver and muscle tissues in animals. It is the energystorage carbohydrate in animals.
Glycogen has a structure similar to amylopectin except
that it is more highly branched with the -1,6glycosidic linkages occurring more frequently along
the polymer chain.
110
Chapter
Outline

Cellulose, like starch and glycogen, is a glucose-based
polymer.
The glucose units in cellulose are join by b-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.
111
Chapter
Outline
Haworth formula
Three-dimensional model of cellulose
112
Chapter
Outline
Cellulose is the most abundant organic substance found

in nature and it is the chief structural component of plants
and wood.
Humans and other animals can not digest cellulose
because their digestive systems do not contain bglycosidases, enzymes that catalyze the hydrolysis of bglycosidic bonds.
Termites have such bacteria in their intestines and can
use wood as their principal food.
Ruminants (cud-chewing animals) and horses can also
digest grasses and hay.
Instead, we have only a-glucosidases; hence, the
polysaccharides we use as sources of glucose are starch
and glycogen.
113
Many bacteria and microorganisms have b-glucosidases.
Chapter
Outline
Acidic Polysaccharides
Acidic polysaccharides: a group of polysaccharides that
contain carboxyl groups and/or sulfuric ester groups, and
play important roles in the structure and function of
connective tissues.
There is no single general type of connective tissue.
Rather, there are a large number of highly specialized
forms, such as cartilage, bone, synovial fluid, skin,
tendons, blood vessels, intervertebral disks, and
cornea.
Most connective tissues are made up of collagen, a
structural protein, in combination with a variety of
acidic polysaccharides.
Chapter
Outline
Hyaluronic acid
Contains from 300 to 100,000 repeating units.
Is most abundant in embryonic tissues and in
specialized connective tissues such as synovial fluid,
the lubricant of joints in the body, and the vitreous of
the eye where it provides a clear, elastic gel that
maintains the retina in its proper position.
D -glucu ronic acid
N-Acetyl-D -glu cosamine
HO
COO
O HO
O
1
CH2 OH
O
1
NH
C
H3 C
O
The rep eating unit of h yalu ronic acid
3
OH
Chapter
Outline
Heparin: a heterogeneous mixture of variably sulfonated
polysaccharide chains, ranging in molecular weight from
6,000 to 30,000 g/mol.
Chapter
Outline
Heparin (contd)
Heparin is synthesized and stored in mast cells of
various tissues, particularly the liver, lungs, and
gut.
The best known and understood of its biological
functions is its anticoagulant activity.
It binds strongly to antithrombin III, a plasma
protein involved in terminating the clotting process.
Chapter
Outline
Complex Polysaccharides
Complex polysaccharides are found in animal tissue
including glycosaminoglycans and antigens.
Glycosaminoglycans are part of the connective tissue
found in joints such as the knee.
These complex polysaccharides act as shock absorbers
between bones.
118
Chapter
Outline
Complex Polysaccharides
Antigens are even more complex polysaccharides and act as
labels to help the immune system differentiate an
animals cells from invading bacteria.
Antigens are found on red blood cells and are used in the
ABO classification system as shown in the Figure on the
next slide . . .
119
Chapter
Outline
Figure 27.10 These are antigens

that are used in the ABO blood
group classification system.
120
Chapter
Outline
Carbohydrates
End

Carbohydrates: Classification and Importance

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Chapter

Carbohydrates: A First Class of

Carbohydrates: A First Class of

Essential components of nucleic acids (D-ribose and

Carbohydrates: A First Class of

Carbohydrates are important in society because they provide:

These classifications are based on the units

Disaccharides are often used by plants and animals to

These carbohydrates also serve as a storage depot for

Figure 7.2. Examples of an aldose (A)

They provide essential structural support for both plant

concentration in the blood: 80-100 mL

Galactose is an aldohexose like glucose and occurs, along

Structure of Glucose and Other Aldoses

Structure of Glucose and Other Aldoses

D-monosaccharide: the -OH on its penultimate

Structure of Glucose and Other Aldoses

Structure of Glucose and Other Aldoses

Structure of Glucose and Other Aldoses

Structure of Glucose and Other Aldoses

Structure of Glucose and Other Aldoses

The enantiomer of Dallose is L-allose.

The enantiomer of Dtalose is L-talose.

Structure of Glucose and Other Aldoses

Structure of Glucose and Other Aldoses

Structure of Glucose and Other Aldoses

Cyclic Structure of Glucose;

Cyclic Structure of Glucose

A five- or six-membered cyclic hemiacetal is represented

A six-membered hemiacetal ring is called a

Enzymes are able to distinguish b/w the 2

Hemiacetals and Acetals

Hemiacetals and Acetals

red raw to show

Hemiacetals and Acetals

Hemiacetals and Acetals

Hemiacetals and Acetals

Hemiacetals and Acetals

Structures of Galactose and Fructose

Structures of Galactose and Fructose

Structures of Galactose and Fructose

most important pentoses

Structures and Properties of Disaccharides

Structures and Properties of Disaccharides

Structures and Properties of Disaccharides

Structures and Properties of Disaccharides

Structures and Properties of Disaccharides

disaccharide with -glycosidic

Sweeteners and Diet

Sweeteners and Diet

Sweeteners and Diet

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Sorbitol is found in the plant world in many berries and

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides

Notice that the product is a carboxylic acid.