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Chapter2 Carbohydrates 1
Chapter2 Carbohydrates 1
Carbohydrates –
Structure and
Function
Chapter 18
Table of Contents
Exercise
Classify each of the following monosaccharides according
to both the number of carbon atoms and the type of
carbonyl group present.
Exercise
Classify each of the following monosaccharides according
to both the number of carbon atoms and the type of
carbonyl group present.
Answers:
a. aldopentose; b.
ketohexose;
c. aldohexose; d.
ketopentose
• Hexoses • D-mannose
• the most common of all the – found in certain bacteria, fungi,
and plants
monosaccharides
– converted to usable glucose in the
• aldohexoses body, but has no real
– D-(+)-mannose physiological significance
– D-(+)-glucose
• A 5% (m/v) glucose solution
is often used in hospitals as
an intravenous source of
nourishment for patients who
cannot take food by mouth.
– D-(+)-galactose
• ketohexose
– D-(-)-fructose
• 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
written to the left.
5. Ketohexose
6. Sweetest of all sugars; the fruit sugar
7. Found in many fruits and in honey
8. Good dietary sugar-- due to higher
sweetness
5. Five membered cyclic form
1. Part of RNA
2. Part of ATP
3. Part of DNA
4. Five membered cyclic form
Oxidation
• Gives three different types of
acidic sugars depending on the
type of oxidizing agent used:
– Weak oxidizing agents like
Tollens and Benedict’s solutions
oxidize the aldehyde end to give
an aldonic acid.
– Strong oxidizing agents can
oxidize both ends of a
monosaccharide at the same time
to produce aldaric acid.
– In biochemical systems enzymes
can oxidize the primary alcohol
end of an aldose such as
glucose, without oxidation of the
aldehyde group, to produce an
alduronic acid.
Reducing sugars
• Sugars with the hemiacetal • Many clinical tests that
structure can be reducing sugars monitor color change are
under alkaline conditions because based on the oxidation
the ring opens forming an
reaction shown here.
aldehyde group.
p622
Section 18.13
Disaccharides
• The two monosaccharides are • Condensation of the hydroxyl
linked together by acetal function of the hemiacetal
formation to form group of one monosaccharide
disaccharide with the hydroxyl group of
• One monosaccharide act as a another monosaccharide
hemiacetal and other as forms the bond, called a
alcohol and the resulting glycosidic bond, joining the 2
ether bond is a glycosidic saccharide units.
linkage.
Invert sugar
• Optical activities:
– Sucrose : +66.5
– Glucose : +53
– Fructose : -92
– Invert sugar : -39
• invert sugar has a much greater • Honeybees and many other
tendency to remain in solution. insects possess an enzyme called
• invertase that hydrolyzes sucrose
In the manufacture of jelly and
to invert sugar.
candy and in the canning of
fruit, crystallization of the sugar • Thus honey is predominantly a
is undesirable, therefore mixture of D-glucose and D-
conditions leading to the fructose with some unhydrolyzed
hydrolysis of sucrose are sucrose.
employed in these processes; in
addition, fructose is sweeter than
sucrose
Copyright © Cengage Learning. All rights reserved 42
Section 18.13
Disaccharides
Practice Exercise
Practice Exercise
Artificial sweeteners
• many monosaccharide
units bonded with
glycosidic linkages
• branched or
unbranched
• homopolysaccharide
or
heteropolysaccharides
Starch
• Amylopectin
– branched chain polymer
– 80 - 85 % of the starch
– the water-insoluble fraction
– composed of 300 –
6000 glucose units
joined primarily by -
1,4- glucosidic bonds
and occasionally by -
1,6- glucosidic bonds
– -1,6 bonds are
responsible for branching
which occurs about
once every 25-30 units.
Copyright © Cengage Learning. All rights reserved 53
Section 18.16
Storage Polysaccharides
Glycogen
• the animal starch
• glucose storage molecule of
animals
• stored in granules in liver and
muscle cells
• like amylopectin, is a nonlinear
polymer of glucose units
joined by -1,4- and -1,6-
glycosidic bonds but has
lower molecular weight
• more highly branched
structure
• its branches are shorter
• gives red-brown color with I2
Copyright © Cengage Learning. All rights reserved 54
Section 18.17
Structural Polysaccharides
Cellulose
Chitin
• Similar to cellulose in both • itself is inert and practically
function and structure insoluble in most solvents. Its
• polymer of N-acetyl-D- derivative, chitosan, can be
glucosamine bound by β-1 4 prepared by simple alkali-
glycosidic linkages (has a linear catalyzed deacylation. Chitosan
extended structure like cellulose) derivatives are commercially used
• as films, fibers, surface coatings
Function is to give rigidity to the
and ultrafiltration membranes
exoskeletons of crabs,
lobsters, shrimp, insects, and
other arthropods
Glycemic Foods
• A developing concern about intake of carbohydrates
involves how fast the given dietary carbohydrates are
broken down to glucose within the human body
• Glycemic index refers to:
– how quickly carbohydrates are digested
– how high blood glucose rises
– how quickly blood glucose levels return to normal
• Glycemic index (GI) has been developed for rating
foods
• Low-GI foods are desirable