Mono, Di

&

Poly
MONOSACCHARIDES
Are simple sugars, they cannot be broken down into other sugars. They are categorized
according to the number of carbons they contain.
Trioses
Is a three-carbon simple sugar.
Formed during the metabolic breakdown of hexose in muscle metabolism. An example;e is
glyceraldehyde (glycerose).
Tetroses
Are four carbon sugars. One tetrose, erythrose, is an intermediate in the hexoses
monophosphate shunt for the oxidation of glucose.
Pentoses
Are five-carbon sugar molecules. The most important of these are ribose and deoxyribose,
which are found in nucleic acids. Ribose forms part of ribonucleic acid (RNA), and
deoxyribose forms part of deoxyribonucleic acid (DNA). Both DNA and RNA are
components of every cell nucleus and cytoplasm. The prefix de- means without, so deoxy-
means without oxygen. Note that deoxyribose has one less oxygen atom than does ribose.
Other pentose of biologic importance include D-ribulose, which is an intermediary in the
pentose phosphate shunt; D-lyxose, which is found in heart muscle; and D-xylose and D-
arabinose, which are components of glycoproteins.
The Fischer projection representations for the pentoses, are called open-chain structures.
However, the predominant form for pentoses is a ring structure.
Recall that all aldehydes react with alcohols to form hemiacetals. In the case of ribose,
Another representation for the hemiacetal (ring) structure of ribose and other
monosaccharides is called the Haworth projection.
In this projection, the ring, consisting of carbons at its corner and an oxygen where
indicated, is considered to be in a plane perpendicular to the paper. The heavy line in the
ring indicates the section closest to you; the lighter line, that part of the ring farther from
you. The ---H and ---OH groups are above and below that plane.
The Fischer and Haworth projections are related as follows;
The groups on the right side of the Fischer projection are written below the plane in the
Haworth projection. Those on the left side are written above the plane.
One exception to rule 1 occurs at carbon 4 in pentoses and at carbon 5 in hexoses
because of the nature of the reaction occurring there. At these carbons, rule 1 is reversed.
At carbon 1 the α form is indicated by the ---OH being written below the plane; the ß form
has the –OH above the plane.
In both projections the CH@OH group, which has no chiral carbon is written as a unit.
Hexoses
The six-carbon sugars, are the most common of all the carbohydrates.
Of the several hexoses, the most important as far as the human body is concerned are;
glucose, galactose, and fructose. All three of these hexoses have the same molecular
formula but have different structural formulars, they are isomers.
Glucose
Medically, when the word glucose is mentioned, the D-isomer is meant because that is the
biologically active isomer. Likewise for the other hexoses, the d_isomer is commonly called
Glucose is known commonly as dextrose, or grape sugar. It is a white crystalline solid that
is soluble in water and insoluble in most organic liquids. It is found, along with fructose,
in many fruit juices. It can be prepared by the hydrolysis of sucrose, a disaccharide, or by
hydrolysis of starch, a polysaccharide.
Glucose is a most important monosaccharide. It is normally found in the bloodstream and
in the tissue fluids. Metabolism of carbohydrates, glucose requires no digestion and can
be given intravenously to patients who are unable to take food by mouth.
Glucose is found in the urine of patients suffering from diabeltes mellitus and is an
indication of this disease. The presence of glucose in urine is called glycosuria. Glucose
may also show up in the urine during extreme excitement (emotional glycosuria), after
ingestion of large amounts of sugar (alimentary glycosuria), or because of other factors on
the metabolism of carbohydrates.
Galacftose,
an isomer of glucose, is also an aldohexose.
Glucose and galactose differ from each other only in the configuration of the H and OH
about a single carbon atom. Two sugars that differ only in the configuration about a single
carbon atom are called epimers. D-galactose is converted into D-glucose in the liver by a
specific enzyme called an epimerase. Galactose is present in some glycoproteins and
glycolipids.
Galactosemia, a severe inherited disease, results in the inability of infants to metabolize
galactose because of a deficiency of either the enzyme galactose 1-phosphate uridyl
transferase or the enzyme galactokinase. The galactose concentration increases in the
Fructose
Is a ketohexose. It can be oresented as a straight-chain or as a ring compound. The ring
structure is predominant. Note that the ring structure represents a hemiketal.
Fructose is often called levulose, or fruit sugar. It occurs naturally in fruit juices and
honey. It can be prepared by the hydrolysis of sucrose, a disaccharide, and also by the
hydrolysis of inulin, a polysaccharide found in Jerusalem artichokes. Fructose is the most
soluble and also the sweetesr of all sugars, being 75 percent sweeter than glucose.
Fructosemia, fructose intolerance, is an inherited disease due to a deficiency of the
enzyme fructose 1-phosphate aldolase. An infant suffering from this disease experiences
hypoglycemia, vomiting and severe malnutrition. Such a condition is treated by placing
the infant on a low-fructose diet.
Reactions of the Hexoses;
Aldehyde + Cu2+ heat acid + Cu2O + water
NaOH
Deep blue solution red-orange precipitate
Oxidation
An aldose contains an aldehyde group, as well as several ---OH groups. If the aldehyde
end of the molecule is oxidized, the product is named an –onic acid. When the aldehyde
end of glucose is oxidized, the product is called gluconic acid. When the aldehyde end of
galactose is oxidized, (the other end of molecule) is oxidized, the product is called a –
uronic acid. The oxidation of the alcohol end of glucose yields glucuronic acid.
Glucuronic acid is a minor product of glucose metabolism. It is also part of the heparin
molecule. Likewise if the alcohol end of galactose is oxidized, galacturonic acid is
Reduction
The aldohexose can be reduced to alcohols. When glucose is reduced, sorbitol is formed.
Sorbitol accumulation in the eye is a major factor in the formation of cataracts due to
diabetes.
Reduction of galactose yields ducitol, and reduction of fructose yields a mixture of
mannitol and sorbitol.
Mannitol is now used in the treatment of malignant brain tumors. Chemotherapeutic
agents are unable to cross the blood-brain barrier, which is the brain’s natural defense
mechanism. The blood-brain barrier allows substances such as glucose, alcohol, and
hallucinogenic agents to pass through, but it inhibits the entry of bacteria and toxic
substances, including chemotherapeutic drugs. However, a high concentration of
manniton can be injected directly into the brain’s main arteries, temporarily shrinking the
cells that line those blood vessels. This shrinkage lowers the blood-brain barrier for
approximately 30 minutes and allows the chemotherapeutic agents to be administered
intravenously.
Fermentation
Glucose ferments in the presence of yeast, forming ethyl alcohol and carbon dioxide. The
reaction will not readily occur in the absence of yeast. Yeast contains certain enzyme that
catalyzes this particular reaction.
Fructose will also ferment, galactose will not readily ferment. Pentose’s do not ferment in
the presence of yeast.
Protein-Sugar Interactions
When plasma glucose concentration is elevated over a period of time, normal hemoglobin
associated with diabetes.
DISACCHARIDES
There are three common disaccharides---sucrose, maltose, and lactose---all of which are
isomers with the molecular formula (C12H22O11). On hydrolysis these disaccharides yield
two monosaccharides.
The disaccharides, just like the monosaccharides, are white, crystalline, sweet solids.
Sucrose is very soluble in water; maltose is fairly soluble; and lactose is only slightly
soluble. The disaccharides are also optically active; they rotate the plane of polarized
light. However, even though they are soluble in water, they are too large to pass through
cell membranes.
Structure
Disaccharides are formed by the combination of two monosaccharides. Monosaccharides
were either hemiacetals or hemiketals. If a hemiacetal or hemiketal ( a monosaccharide )
combines with an alcohol ( another monosaccharide), an acetal or a ketal will be formed.
Such a bond between the two monosaccharides is called a “ glycosidic linkage.
Reducing properties
In maltose the aldehyde groups are at carbon 1 in each of the original glucose molecules.
Since the linkage is 1,4, one free aldehyde group remains. Therefore, maltose acts as a
reducing sugar.
In sucrose, the glucose part had the aldehyde at carbon 1, and the fructose part had the
ketone group at carbon 2. Since the linkage is 1,2, neither group is free. Therefore,
sucrose is not a reducing sugar.
Fermentation
Sucrose and maltose will ferment when yeast is added because yeast contains the enzymes
sucrose and maltase; lactose will not ferment when yeast is added because yeast does not
contain lactase. The identity of a disaccharide can be deduced on the basis of its
fermentation reaction and its reducing properties.
Sucrose
is the sugar used ordinarily in the home. It is also known as cane sugar. Sucrose is
produced commercially from sugar cane and sugar beets. It also occurs in sorghum,
pineapple, and carrot roots.
A sugar beet is a plant whose root contains a high concentration of sucrose and which is
grown commercially for sugar production. In plant breeding it is known as the Altissima
cultivar group of the common beet (Beta vulgaris).
Species: Beta vulgaris
Subspecies: Beta vulgaris subsp. Vulgaris
Cultivar group: Altissima Group

When sucrose is hydrolyzed, It forms a mixture of sucrose and fructose. This 50:50
Maltose
Commonly known as malt sugar, is present in germinating grain. It is produced
commercially by the hydrolysis of starch.
Lactose
Commonly known as milk sugar, is present in milk. It differs from the preceding sugars in
that it has an animal origin. Certain bacteria cause lactose to ferment, forming lactic acid.
When this reaction occurs, the milk is said to be sour. Lactose is used in high-calcium diets
and in infant foods. Lactose can be used for increasing calorie intake without adding much
sweetness. Lactose is found in the urine of pregnant women and since it is a reducing
sugar, it gives a positive test with Cu2+ complex ions.
Sweetness and Sugar Substitutes
When we speak of sugar, we think of a substance with a sweet taste. However,, when
sweetness is not a specific property of carbohydrates. Many sugars have some degree of
sweetness, but several synthetic compounds have much more sweetness without any
calories.
Relative Sweetness of Sugars and Other compounds
Fructose 175 Maltose 32
Galactose 32 Sucrose 100
Glucose 75 Aspatame 15,000
Lactose 16 Cyclamate 3,000
Saccharin 35,000
'The Val Sweetness Scale' was created to measure sweetness, and indicates the
sweeteners concentration through a numeric unit. The point at which sweetness is felt is
the sensitivity threshold, and is defined as one Val. Twice the sweetness is two Val and so
on.
Valiber developed a patent pending universal method and system for communicating
sensations in general, and sweetness in particular – ‘The Val Sweetness Scale’.
Because of the greater sweetness of fructose, this substance is used in some low-calorie
foods because less is needed to provide the same level of sweetness.
Cyclamates were first marketed in 1950, but after 1969 findings that large doses caused
cancer in rats, they were banned in the United States, although they are still in use in
Canada. There has never been a connection between cyclamates and cancer or any other
disease in humans.
The wide acceptance of aspartame is partially attributable to its lack of a bitter aftertaste,
as is associated with saccharine. Aspartame is hydrolyzed to aspartic acid, phenylalanine
and methanol Studies have indicated that aspartame is safe, and only those persons on a
low phenylalanine diet need to avoid it.
Polysaccharides
Are polymers of monosaccharides. Complete hydrolysis of polysaccharides produces many
molecules of monosaccharides. The polysaccharides differ from monosaccharides and
disaccharides in many ways.
Comparison of Polysaccharides with Monosaccharides and disaccharides
Property Monosaccharides Polysaccharides
And Disaccharides

Molecular Mass Low Very high

Taste Sweet Tasteless

Solubility in water Soluble Insoluble

Size of particles Pass through a membrane Do not pass through a membrane

Test with Cupper 2+

complex ions (an Positive (except for sucrose) Negative
oxidizing agent)
Polysaccharides can be formed from pentoses (five-carbon sugars) or from hexoses (six-
carbon sugars). Polysaccharides formed from pentoses are called pentosans. Those
formed from hexoses are called hexosans ( or sometimes glucosans).
The hexosans (or glucosans) are the most important in terms of physiology. The hexosans
have the general formula (C6H10O5)x, where x is some large number. Some of the
common hexosans are starch, cellulose, glycogen and dextrin. All are made up of only
glucose molecules.
Starch
Plants store energy primarily in the form of starch granules. Starch is actually a mixture
of the polysaccharides amylopectin and amylose. Amylopectin is a branched
polysaccharide present in starch to a large extent of 80 to 85 percent. It is usually
present in the covering of the starch granules. ASmylose is a nonbranched
polysaccharides present in starch to an extent of 15 to 20 percent.
Starch is insoluble in water. When starch is placed in boil;ing water, the granules rupture,
forming a paste that gels on cooling. When an small amount of starch is added to a large
amount of boiling water, a colloidal dispersion of starch in water formed. Starch gives a
characteristic deep blue color with iodine. This test is used to detect the presence of
starch because it is conclusive even when only a small amount of starch is present. That
is if iodine is added to an unknown and a blue color is produced, starch is present. This
test can also be used to check for the presence of iodine. If starch is added to an
unknown and a blue color is produced, iodine must be present.
When starch is hydrolyzed, it forms dextrins(amylodextrin, erythrodextrin),
iodine is added.
Cellulose
Wood, cotton and paper are composed primarily of cellulose. Cellulose is the supporting
and structural substance of plants. Like starch, cellulose is a polysaccharide composed of
many glucose units. It is not affected by any of the enzymes present in the human
digestive system and so cannot be digestesd. However, it does serve a purpose when
eaten with other foods; it gives bulk to the feces and prevents constipation.
Cellulose does not dissolve in water or in most ordinary solvents. It gives no color test
with iodine and gives a negative test with Cu2+ complex ions.
Cotton is nearly pure cellulose. When cotton fibers are treated with a strong solution of
sodium hydroxide and then stretched and dried, the fibers take on a high luster. Such
cotton is called mercerized cotton.
Cellulose is also used to make rayon. In this process, purified wood pulp (nearly pure
cellulose) is converted into a viscous liquid called viscose by treatment with sodium
hydroxide and carbon disulfide. When the viscose is forced through small openings in a
block suspended in an acid solution, the cellulose is regenerated into fibers that can then
be formed into threads.
Glycogen
Is present in the body and is stored in the liver and the muscles, where it serves as a
reserve supply of glucose. Glycogen has an animal origin, as opposed to the plant origin
of starch. The structure of glycogen is similar to that of amylopectin but not as branched.
Glycogen forms a colloidal dispersion in water and gives a red collar with iodine. It gives
glycogenesis. When glycogen is hydrolyzed into glucose, the process is called
glycogenolysis.
Adrenaline
Adrenaline, also known as epinephrine, is a hormone and medication. Adrenaline is
normally produced by both the adrenal glands and a small number of neurons in the
medulla oblongata where it acts as a neurotransmitter involved in regulating visceral
functions.
Key actions of adrenaline include increasing the heart rate, increasing blood pressure,
expanding the air passages of the lungs, enlarging the pupil in the eye (see photo),
redistributing blood to the muscles and altering the body's metabolism, so as to maximize
blood glucose levels (primarily for the brain).
Physicians once believed that the adrenaline that flooded the system caused an extra
boost to the muscles, allowing people to be stronger. But that's not quite accurate. ... And
while the adrenaline fueled fight-or-flight reflex spurs people into action, the body's entire
stress response contributes to superhuman strength.
Epinephrine, more commonly known as adrenaline, is a hormone secreted by the medulla
of the adrenal glands. Strong emotions such as fear or anger cause epinephrine to be
released into the bloodstream, which causes an increase in heart rate, muscle strength,
blood pressure, and sugar metabolism.
Dextrin
Is produced during the hydrolysis of starch. Dextrin is an intermediate between starch
and maltose. It forms sticky colloidal suspensions with water and is used in the
Heparin
Is a polysaccharide used as blood anticoagulant. It accelerates the inactivation of
thrombin and other blood-clotting agents. The structure of Heparin consists of repeating
units of glucuronic acid and glucosamine with some sulfate groups on the amino and
hydroxyls groups. Heparin is the strongest organic acid present in the body.
Warfarin
is an anticoagulant (blood thinner). Warfarin reduces the formation of blood clots.
Warfarin is used to treat or prevent blood clots in veins or arteries, which can reduce the
risk of stroke, heart attack, or other serious conditions.
Although warfarin can be a lifesaver by preventing blood-clots, it was used to kill rats and
even though it can help humans there still are strong side-effects including spontaneous
heavy bruising, internal bleeding and hair loss that need to be closely monitored by
doctors.
Dextran
Dextran (not the same as dextrin) is a polysaccharide produced by certain bacteria when
they grown on sucrose. There are various types of dextrans, differing in chain lenth and
degree of branching. Medicinally, dextrans are used as blood extenders to hold water in
the bloodstream and help prevent drops in blood volume and blood pressure. Dextrans
growing on the surfaces of teeth are an important component of dental plaque.
STRUCTURAL FORMULAS
Maltose is composed of two molecules of glucose. Sucrose is composed of one molecule of
glucose and another of fructose (fructose is a monosaccharide). Lactose is composed of
Family of Aldoses