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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.
1. Ketohexose
2. Sweetest of all sugars; the fruit sugar
3. Found in many fruits and in honey
4. 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 monitor
structure can be reducing sugars color change are based on the
under alkaline conditions because oxidation reaction shown here.
the ring opens forming an
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 disaccharide group of one monosaccharide
• One monosaccharide act as a with the hydroxyl group of
hemiacetal and other as another monosaccharide forms
alcohol and the resulting ether the bond, called a glycosidic
bond is a glycosidic linkage. bond, joining the 2 saccharide
units.
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 is • Thus honey is predominantly a
undesirable, therefore conditions mixture of D-glucose and D-
leading to the hydrolysis of fructose with some unhydrolyzed
sucrose are employed in these sucrose.
processes; in addition, fructose is
sweeter than sucrose
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 49
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
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
• Function is to give rigidity to the as films, fibers, surface coatings
exoskeletons of crabs, lobsters, and ultrafiltration membranes
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