Biochemistry

DISACCHARIDE AND POLYSACCHARIDE PDF

Disaccharides
Hemiketal They generally result from the addition of
an alcohol to an aldehyde or a ketone,

C12H22O11 although the latter are sometimes called

hemiketals. Most sugars are hemiacetals.
• Just like monosaccharide, disaccharide are white,
crystalline, sweet solids.
• On hydrolysis disaccharides yield two
monosaccharides.
o Hydrolysis
- is a chemical reaction which a molecule of water
breaks one or more chemical bond
- water is nucleophile, which form bonds by
donating an electron pair.
▪ Digestion
▪ Absorption
▪ Elimination
▪ Substitution
Common Example Solubility
disaccharide
Sucrose Table sugar Very soluble
Maltose Malt sugar Fairly soluble
Lactose Milk sugar Slightly soluble Combination of a molecule of α -glucose with
molecule of β -glucose. The product of such
reaction are B- maltose and water
hydrolysis
C12H22O11 C6H12O6 C6H12O6
A A A
disaccharide monosaccharide monosaccharide
Sucrose Glucose Fructose
Maltose Glucose Glucose
Lactose Glucose Galactose

Disaccharide
• Formed by the combination of 2 monosaccharides.
Glycosidic - It is a bond between 2 monosaccharides.
Linkage - When hemiacetal/hemiketal
(monosaccharide) combines with alcohol
(monosaccharide) an acetal or ketal will
be formed
• Acetal are geminal-diether
derivatives of aldehydes or ketones,
formed by reaction with two
equivalents (or an excess amount) of
an alcohol and elimination of water.
Ketone derivatives of this kind were
once called ketals, but modern usage
has dropped that term
Hemiacetal a molecule made up of a
core carbon atom
connected to four groups:
–OR, –OH, –R, and –H.
•
• α -1,4 linkage- the linkage in β -maltose is between
carbon 1 of one glucose and 4 carbon of the other
glucose
• β -1,4 Glycosidic linkage (cellobiose) is formed when
a molecule of β -glucose combined with another β -
glucose,
Enzyme glycosidic linkage
- It is a specific in type of glycosidic linkage α or β
whose hydrolysis can catalyze
- An enzyme that catalyzes the hydrolysis of β-
Glycosidic linkage catalyzes the hydrolysis of
cellobiose
β- Glycosidic - It is not found in human digestive
linkage system.
hydrolysis of - The reason why human cannot digest
enzymes cellulose and cellobiose, both have
β- Glycosidic linkage

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DISACCHARIDE AND POLYSACCHARIDE PDF

Glycosidic Linkage of α-glucose and β -fructose

• Sucrose and water are Reducing Property
the product of the Linkage Reducing description
reaction Property
Sucrose 1,2 Not • The glucose part
reducing had aldehyde at
sugar carbon 1
• The fructose
part had ketone
in carbon 2
Maltose 1,4 Reducing • The aldehyde
sugar group are at the
carbon 1 in each
original glucose
Lactose 1,4 Acts as a • Both aldehyde
reducing group were on
sugar carbon 1, and the
other molecule is
free to react.

• The linkage is α -1,2 glycosidic linkage because it
occurs between carbon 1 of the glucose molecule and
carbon 2 of the fructose
There is only one form of sucrose; α and β forms do
not exist.
Glycosidic Linkage of β -galactose and molecule of
glucose α and β
• The products are water and lactose (α and β)
• The linkage is 1,4
Fermentation
• Sucrose and Maltose
- It will ferment when yeast is added because yeast
contains the enzymes sucrase and maltase.
• Lactose
- It will not ferment because yeast doesn’t contain
lactase
Sucrose
• The sugar used ordinarily in the home
• Also known as cane sugar
• Produced commercially from sugar cane and sugar
beets. It can also occur in sorghum, pineapple, and
carrot roots.
• When hydrolyzed, it forms a mixture of glucose and
fructose.
• invert sugar
- The mixture of glucose and fructose
- It reverses the rotation of polarized light.

Maltose
• Known as malt sugar.
• It is present in germinating grain
• It is produced commercially by hydrolysis of starch

Lactose
• Known as milk sugar; Present in milk
• Differs from the percentage of sugar depend in
the animal origin
• Used in high-calcium diets and infant foods
• Can be used for increasing the calorie intake
without adding much sweetness.
• Can be found in the urine of a pregnant women and
because it is a reducing sugar, it gives positive test
with Cu2+ complex ions

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Lactic acid Forms when a certain bacteria

cause lactose to ferment
Sweetness and sugar substitute Starch
• Sweetness is not a specific property of carbohydrates. - plant store energy primarily in the form of starch
Cyclamates It was first marketed in 1950, granules
but after 1969 findings that - it is the mixture of the polysaccharide amylopectin
large doses cause cancer in rats, and amylose.
they were banned in the USA. Amylopectin - A branched polysaccharide
But still used in the Canada. presents in starch to large
Aspartame Hydrolyzed aspartic acid, extent 80-85
phenylalanine, and methanol - It is usually present in the
covering of starch granules
Amylose - Non branched polysaccharide
Relative sweetness of sugar and
presents to starch to an extent
other compounds
of 15-20 percent.
Fructose 175
- insoluble in water, when place in boiling water; the
Galactose 32
granules rupture forming paste that gels on cooling.
Glucose 75
Colloidal - it formed in the starch in
Lactose 16
dispersion water, when a small amount of
Maltose 31
starch added to a large amount
Sucrose 100
of water
Aspartame 15,000
- it gives a characteristic deep blue color with iodine
Cyclamate 3000
* the test was used to detect the presence of
Saccharin 35,000
starch because it is conclusive even when only a
small starch is present.
Polysaccharide * It can also used to be check for the presence of
iodine
• Polymers of monosaccharide
- In hydrolysis, it forms dextrin (amylodextrin,
• Complete hydrolysis of polysaccharide produces many
erythrodextrin, anchroodextrin) then maltose, and
molecules of monosaccharide.
finally glucose.
Property Monosaccharides Polysaccharides
Starch Erythrodextrin Maltose Glucose
and disaccharide
Blue red colorless colorless
Molecular Low Very high
Mass
Cellulose
Taste Sweet Tasteless - Wood, cotton, and paper
Stability in Soluble In soluble - It is the support and structural substance of plants
water - It is a polysaccharide composing many glucose unit.
Size of Pass through Do not pass - It is not affected by any of enzyme present in the
Particles membrane through human digestive system and cannot be digested.
Test with Positive except for negative - It gives bulk to feces and prevent constipation.
Cu2t sucrose - Not soluble to water or in most ordinary solvents
complex ion * It gives no color with iodine and gives negative
an oxidizing with Cu2+complex ions
agent Cotton - Nearly pure cellulose
• Can be formed from pentoses-pentosans (five-carbon - Mercerized cotton is cotton
sugar) or from hexoses-hexosans/glucosan (six-carbon fibers that have luster. It
sugar) happened when cotton fibers
Hexosans/ Glucosans were treated with sodium
• general formula: where x is some large number hydroxide and then stretched

(C6H10O5) x Rayon
and dried
- Purified wood pulp (nearly pure
• it is the most important in terms of physiology
cellulose) into a viscous liquid
EXAMPLES o Starch
called viscose by treatment with
o Cellulose
sodium hydroxide and carbon
o Glycogen
disulfide.
o dextrin
- The viscose is forced through
small openings in a block

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suspended in an acid solution, Other terms

the cellulose is regenerated into Dextrin − Produced during the hydrolysis of starch
fibers that can be formed into − An intermediate between starch and
thread. maltose
− Used when digestion of starch might be a
Glycogen problem, as with infants and elderly
- It is present in the body and stored in the liver and persons
muscles, where it serves as a reserve supply of − Forms a sticky colloidal suspension with
glucose. water and used in the preparation of
- It has an animal origin, as opposed to the plant origin adhesives.
of the starch * Glue on the back of a postage stamps
- The structure is similar to amylopectin but not as is a dextrin
branched. Heparin − Used as a blood anticoagulant
- It forms a colloidal dispersion in water and gives red − Accelerates the inactivation of thrombin
color with iodine and other blood-clotting agents
- No test with alkaline Cu2+complex − Its structure consists of repeating units
Glycogenesis - A process when glycogen of glucuronic acid and glucosamine with
formed in the body cells from some sulfate groups on the amino and
molecules of glucose. hydroxyl group
Glycogenolysis - A process when glycogen is − It is the strongest organic acid present in
hydrolyzed into glucose the body

Glycogenesis
Glucose Glycogen
glycogenolysis

Difference between amylose and cellulose

Amylose has α -1,4 linkage between glucose units,
whereas cellulose has β -1,4 Glycosidic linkage
between glucose units
Glycogen is highly more branched
Dextran − Not the same as dextrin
− Produced by certain bacteria when they
are grown on sucrose
− Medically: used as blood extenders to hold
water in the blood stream and prevent
drops in blood volume and pressure
− Growing on the surfaces of teeth are
important component of dental plaque

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Summary o Hexoses will ferment in the presence of enzymes

• Carbohydrates are polyhydroxy aldehydes/ found in yeast
polyhydroxy ketones, substances that yield these • Disaccharide on hydrolysis yields 2 monosaccharides.
compounds on hydrolysis. • The common disaccharide are isomers with the molecular
o Hydrolysis involves the reaction of an organic formula (C12H22O11)
chemical with water to form two or more new o Sucrose
substances and usually means the cleavage of - Not a reducing sugar
chemical bonds by the addition of water. - It will ferment with yeast, owing to the presence of
• Carbohydrates are divided into 3 categories: the enzymes sucrase
o Monosaccharide o Maltose
o Disaccharide - Show reducing properties with alkaline Cu2+ complex
o Polysaccharide ions.
• Stereoisomers are compound that have the same - It will ferment with yeast, owing to the presence of
molecular formula but different structure that are the enzyme maltase
mirror images of one another o Lactose
o Enantiomers are mirror images of one another - Show reducing properties with alkaline Cu2+ complex
o Diastereomers are not mirror images ions.
o Chiral is a property of an item that cannot be same - Not fermenting because of the absence of enzyme
on its mirror image lactase
• The parent compound of enantiomers glyceraldehyde • Polysaccharide are polymers of monosaccharides and
• Photosynthesis is a process where the plants formed yield monosaccharides when hydrolyzed.
carbohydrates o They have high molecular mass
o Plants cells takes carbon dioxide from the air and o Insoluble in water
water from the ground and combine them in the o Tasteless
presence of sunlight and chlorophyll to produce o give negative test for reducing sugars
monosaccharides, at the same time giving off oxygen o opposite of mono and di
into the air o there are 3 common polysaccharides
o Plant cells also have the ability to convert the ▪ starch-plants store their foods
monosaccharide thus Formed into disaccharide and ▪ cellulose-plants use as support and structure
polysaccharide. ▪ glycogen- animals use it as reserve supply of
o Carbohydrates are catabolized in the body, carbon carbohydrate
dioxide and water are formed, thus returning these
substances for reuse by plants.
• Monosaccharide, or simple sugars are either aldoses or
ketoses, depending upon whether they contain an
aldehyde and a ketone group
o Hexoses is 6-carbon monosaccharide that is the most
common in terms of the human body
o The most important hexoses in the body (C6H12O6)
▪ Glucose
- Is an aldohexose whose structure may be
represented as linear or ring-shaped molecule
- Commonly known as dextrose or grape sugar
- The most important monosaccharide because and
normally found in the bloodstream and in the
tissue fluids
▪ Fructose
- Ketohexose, commonly known as levulose, or fruit
sugar
- The sweetest of all sugar
- Occurs in nature as one constituents of sucrose
and is found free in fruit juices and in honey
▪ galactose
- Also, an aldohexose. It occurs in nature as one of
the constitutes of lactose.
o Hexoses is either aldehydes or ketones and can act as
reducing agents