UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
COURSE OUTLINE: PRELIMS
1.
2.
3.
4.
5.
BIOMOLECULES
Carbohydrates
Monosaccharide
Oligosaccharides
Disaccharides
Polysaccharides
Biomolecules
● is chemical compound fond in living organisms.
● Micro-molecule/monomers
● Macromolecules/polymers:
● mainly composed of
REFERENCE BOOK
o
o
o
o
SLRM. Youtube
byjus.com
Chapter 3: Carbohydrates ppt.
Pharmaceutical Biochemistry


METABOLISM


Metabolism
● Metabolism is the process by which your body

converts what you eat and drink into energy.

●
During this complex process, calories in food and
beverages are combined with oxygen to release the
energy your body needs to function.
●
The chemical changes that take place in a cell or
organism. These changes make energy and the,
materials cells and organism need to
o Grow
o Reproduce
o Stray healthy
Carbohydrates/ Sugar
Lipid/ Fatty Acid
Protein/ Amino Acid
Nucleic acid/ DNA,RNA
All living organism contain a high level of chemical…
All living organism have systems of extracting,
transforming, and using energy for the environment.
All living organism have all function
All living organism have mechanism for sensing, and
responding to alterations in their surroundings.
All living organisms has the capacity for precise selfreplication and self- assembly.
All living organism has the capacity to change overtime
by gradual evolution.
MAJOR TYPES

METABOLISM can be DIVIDED INTO TWO
1.
CATABOLISM- The breakdown
2.
molecules to obtain energy.
ANABOLISM- The synthesis
compounds needed by the cells.
of
Carbohydrates
Cn(H2O)n

●
of
●
all
Lipid
●
●
●
●
Protein
●
●
●
A group of organic compounds
occurring in living tissues and
foods in the form of starch,
cellulose, and sugars. (includes
sugars, fibers, and starches)
Main source of energy for your
body’s cell, tissues,and organs.
Examples
o Grains
o Vegetables and Fruits
o Milk and Dairy products
Organic compounds that is nonpolar molecules, soluble only on
non-polar solvents and insoluble in
water.
composed of fats and oils.
Can be synthesized in the liver.
Examples
o oil and Butter
o Whole milk
o Cheese and fried foods
large molecules composed of basic
unit called amino acids.
proteins contain carbon, hydrogen,
oxygen, nitrogen, and sulfur.
Example
o Animal- based foods
o Meat and fish
o Cheese, egg, beans
o Nuts and seeds
Metabolism also help get rid of toxic substances.
-1-
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
Nucleic
Acid




●
are made of carbon, hydrogen,
oxygen,
nitrogen,
and
phosphorus.
store and transfer cellular
information and energy in all
living organism.
They carry the genetic blueprint
of a cell and carry instructions for
the functioning of the cell
Example: DNA AND RNA
●
●
A.TRIOSE AS MONOSACCHARIDES
Smallest/ simplest monosaccharide
● D-GLYCERALDEHYDE

Aldotetrose
- D-erythrose
- D-threose
PRIMARY ENERGY SOURCE OF ORGANS
 They are called carbohydrates as they
comprise carbon, hydrogen and oxygen at their
chemical level.

Aldopentose
- D-ribose
- D- arabinose
- D- xylose
- D- lyxose
 A source of energy for the cells, organs and tissues.
The extra amount of energy or sugar is stored in our
muscles and liver for further requirement.

Aldohexose
- D- allose
- D- altrose
- D- glucose
- D- mannose
- D- gulose
- D- iodose
- D- galactose
- D - talose
MONOSACCHARIDES
●
●
●
●
●
and
DIHYDROXYACETONE

Aldotriose
- D-glyceraldehyde
CARBOHYDRATE
●
Other examples of monosaccharides include,
mannose, galactose, fructose, etc.
Glucose, fructose,galactose
Saccharides in 3-7 carbon atoms are commonly
found in nature.
Are poly-hydroxy-aldehydes or ketones, generally
with an unbranched C- chain.
Most basic form of carbohydrates.
By functional group aldose and ketose (polyhydroxylated, meaning a lot of OH group)
By no. of carbon
o 3c- triose (e.g.Glyceraldehyde)
o 4c- tetrose
o 5c- pentose
o 6c- hexose
The main function of monosaccharides is to produce
and store energy.
A sugar that is not decomposable into simpler sugars
by hydrolysis
-2-
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
2. D-Glucose
• Most abundant in nature and the most important from a
human nutritional support.
• Tastes sweet, and are important in nutritional diet
• (L-glucose are tasteless and are not essential in the body)
• Present in ripe fruits particularly grapes (20-30% glucose
by mass)
• Termed as grape sugar
• SYNONYM: Blood sugar and Dextrose
• 2 hormones essential in keeping the glucose
concentration in blood normal: • Insulin• Glucagon
• DIABETES MELLITUS- uncontrolled inc of Blood sugar
3. D-Galactose
• D-Galactose vs D-Glucose are EPIMERS (diastereomers
that differ on in the configuration at one chiral center)
• Synthesized from glucose in the mammary gland for use
in lactose(milk sugar)
• Disaccharide consisting of 2 glucose units
• Also known as Brain Sugar because it is a component of
glycoproteins found in the brain and nerve tissue
• Also present in chemical markers to distinguish types of
blood (A,B, AB and O)
4. D-Fructose
• Biochemically the most important ketohexose
• Also known as levulose (are used to describe D- fructose
to rotate on the left in a plane polarized light) and fruit
sugar(present in fruit and honey)
• Sometimes used as a dietary sugar (less amount of
sweetness)
5. D-Ribose
• A pentose
• Component of a variety of complex molecules including
RNA and ATP
• 2-deoxyD-ribose is important in nucleic acid chemistry

Ketotriose
- Dihydroxyacetone

Ketotetrose
- D-erythulose
C. MONOSACCHARIDE DERIVATIVES

Ketopentoses
- D- xylulose
- D- ribulose
• Acidic Sugars (obtained by oxidation)
• D-Gluconic acid (Aldonic Acid-top)
• D-Glucoronic acid (Alduronic Acid-bottom)
• D-Glucaric acid (Aldaric Acid-top and bottom)
• Sugar alcohols (obtained during reduction)
• D-Glucitol (Alditol-alcohol group is on top and bottom)
• Glycoside (reaction with alcohol)
• Phosphate esters
• a-D-Glucose-6-phosphate
• Amino Sugars
• a-D-Glucosamine

Ketohexoses
- D- tagatose
- D- sorbose
- D- psicose
- D- fructose
PART 3: REACTIONS OF MONOSACCHARIDES
B.Biochemically important Monosaccharides
• Five important reactions:
• Oxidation to acidic sugars
• Reduction to sugar alcohols
• Glycoside formation
• Phosphate ester formation
• Amino sugar formation
• D-Glyceraldehyde and Dihydroxyketone
• D-Glucose • D-Galactose • D-Fructose • D- Ribose
1. D-Glyceraldehyde and Dihydroxyacetone
• The Simplest of the monosaccharides
• Important in the process of GLYCOLYSIS(reaction where
glucose is converted into 2 molecules of pyruvate.
• Chiral: D-Glyceraldehyde
• Achiral: Dihydroxyacetone


-3-
Also known as “simple sugar”
CnH2nOn- basic formula for monosaccharides.
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE



Cn(H2O)n- generic formula
Classification is done via # units
Glucose and fructose are the most available
monosaccharide in nature.
B(1- 4)
glycosidic
linkage
OLIGOSACCHARIDES
2-10 Units of sugar
● Act as prebiotic
● Classes:
o Disaccharides and Polysaccharides

*2 Units DISACCHARIDES
Formed by 2 monosaccharides.
Simple carbohydrate, function is to provide your
body with quick source of energy.
o Sucrose, maltose and lactose.
●
●


Bonds present: Glycosidic bonds(the bond between
hydroxyl groups of the monosaccharides) A-glycosidic
bonds • B-glycosidic bonds
Disaccharides: • Maltose • Cellobiose • Lactose •
Sucrose
3 DISACCHARIDES
MALTOSE
C12H22O1
1
Glucose
+
Glucose
Aglycosidic
bond:
A(1,4),Dglucose
LACTOSE
C12H22O11
Glucose
+
Galactose
SUCROSE
• Also known as malt sugar
• Produced during degradation of starch
in plants when seeds germinate and in
human during starch digestion
• Common ingredient in baby foods in
the form of malted milk
• Malt(germinated barley)
• Reducing sugar
• Chemical reaction: Oxidation and
HYDROLYSIS
• Acidic derivative of Maltose is maltase
(an enzyme in human body and yeast)
needed
for
metabolism
of
CARBOHYDRATES
● Examples
o Grains
o Vegetables and Fruits
o Milk and Dairy products
C12H22O11
Glucose
+
Fructose
a,b(1-2)
glycosidic
bond
●
●
Discovered by Fabriccio Bartoletti
Commonly used in the pharmacy
sector for manufacturing tablets
● Produce in the small intestine.
• B-D-galactose and D-glucose in
• Major sugar found in milk
• Also known as milk sugar
• Most important ingredient found in
formula milk to mimic mother’s milk
CELOBIO
SE
B(1,4)
• Lactic acid-product when milk gets
sour due to bacteria
• Pasteurization of milk includes heating
that kills bacterial growth
• Enzyme: Lactase- an enzyme needed
to metabolize lactose to glucose ang
galactose
•
Genetic
condition:
LACTOSE
INTOLERANCE
• Genetic defect
• Physiological decline with age
• Injuries of the mucosal lining of the
intestines
• Symptoms:
• Fullness, discomfort , cramping,
nausea an diarrhea.
• Conversion of lactose to lactic acid in
the intestine
• GALACTOSEMIA- genetic condition
that metabolizes Galactose in the body
• Galactose derivative called “galactitol”
accumulates in the blood causing
mental retardation and death in infants
● Examples
o yoghurt
o milk, cream
o Cheese
• Also known as Table sugar
• Most abundant disaccharides that
occurs kingdom throughout the plant
• extraction of sugar cane and sugar
beets
• Sugar cane: 20% by mass of sucrose
• Sugar beets: 17% by mass of sucrose
• Combination of a-D-glucose and b- Dfructose
• Non-reducing sugar
• Enzyme: Sucrase- breaks the a,b (12) glycosidic linkage present in human
body
• Sucrose hydrolysis happens during
digestion and the product is an
“inverted sugar”
• Can also be achieved when making
jam
● It serves as chemical intermediate
for many emulsifying agents and
detergents. Also serves as
antioxidant
● Example
o sugar cane
o Sugar beets
o bananas, grapes, carrots
• A product in the hydrolysis
POLYSACCHARIDE
• Reducing sugar
• Ezyme derivative : cellobiase
of
POLYSACCHARIDES
ALSO CALLED “GLYCANS”
-4-
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
10 Units POLYSACCHARIDES

important source of energy in animal cell and form
a structural component of plant cell. It can be a
homopolysaccharide or a
heteropolysaccharide depending upon the type
of the monosaccharides.

●
●
Due to the presence of multiple hydrogen bonds,
the water cannot invade the molecules making
them hydrophobic.
●
Storage Polysaccharide
●

Polysaccharide that is a storage form for
monosaccharides and is used as an energy
source in cells

To lower the osmotic pressure within cells

Starch in plant cells

Glycogen in animal and human cells
●
Example
o Starch, glycogen, and cellulose
o Starch- is composed of two componentsamylose forms the linear chain and
amylopectin is a much-branched chan.
o Glycogen- is called animal starch, similar to
starch but has more extensive branching.
o Cellulose- is a structural carbohydrates and
is the main structural component of the
plant cell wall.
Homopolysaccharide
●
●
●
●
A polysaccharide
that contains the
same type of
monosaccharide.
are chemical
compounds that
are composed of a
single type
monomer.
have simple
structure
Examples:
● Glycogen- made
up of a large chain
of molecules,
found in animals
and fungi
● Cellulose- cell all
of the plant, long
chains of Bglycosides.
● Starch- formed by
the condensation
of amylose and
amylopectin, found
in plants, fruit
seeds, etc.
A.
Starch
2 different polyglucose polysaccharide can be isolated
from most starch:
Heteropolysaccharide
●
●
A
homopolysacchari
de that contains
glucose
Acts as an
energy storage in
plants
Excess glucose
are converted into
starch and stored
for future use
In times that the
cell cannot
generate energy
from absorbed
glucose,
hydrolysis of
starch is needed
to generate energy
Insulin- made up
of number of
fructofuranose
molecules linked
together in chains.
Found in the
tubers of dahlia,
artichoke, etc.
A polysaccharide
that contains
different type of
monosaccharides.
made out of two or
more. different
monosaccharides
Examples:
● Hyaluronic Acidmade up of Dglucuronic acid
and N-acetylglucosamine.
Found in
connective tissue
and skin.
● Heparin- made up
of D-glucuronic
acid, L-iduronic
acid, N-sulfo-Dglucosamine is
largely distributed
in mas cells and
blood.
● Chondroitin-4sulfate-
AMYLOSE
AMYLOPECTIN
straight
chain
glucose
polymer in 15-20% of the
starch
•300500monomerunitsareprese
nt
• a(1-4)
branched glucose polymer
in 80-85% of the starch
• Appear once in every 2530 glucose units
•Involves100,000 glucose
units
• a-(1-4),(1-6)
• Both are broken down into simpler units through hydrolysis
within the digestive tract through enzymes.
• Present in potatoes and cereal grains that accounts at least
2/3rds of the world’s food consumption
B.
Glycogen
• Excess glucose from diet are converted to glycogen
during blood glucose drops (exercise and fasting) some
stored glycogen are hydrolyzed back to glucose
• Glycogenesis-glucose to glycogen
• Glycogenolysis-glycogen to glucose
• Also referred as animal starch
• Stores polysaccharide in animals and in humans
• Located on liver cells and muscle cells
• a-glycosidic linkage in (1,4) and (1,6) like an
amylopectin but glycogen has larger amounts of glucose
units (1,000,000)
-5-
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
A.
• Best known heparin’s biochemical function is an
anticoagulant-helps to prevent clots.
•N-sulfo-D-glucosamine-6-sulfate and D-glucoronate-2sulfate
• Small polysaccharide with 15-90 disaccharide per chain
Cellulose
•Structural component of plant cell walls
• Woody portions of plants, stems, stalks
and trunks
• Fibrous and water soluble
• Unbranched glucose polymer
• B(1,4) glycosidic bonds
• Spiral like structure
• Contains 5000 glucose units
• Cotton(95%cellulose)
• Wood(50%cellulose)
• Structural Polysaccharides
• Polysaccharide that serves as structural element in plant
cell walls and animal exoskeleton.
• Examples: Cellulose and Chitin
The structures of Carbohydrates
THE FISCHER
PROJECTION
A.
• Not a source of nutrition in humans because humans
lack an enzyme that hydrolyzes b(1,4) linkages of
cellulose
• Cellulase-an enzyme that bacteria produce to hydrolyze
cellulose
• Located at the intestines of animals
• Converts cellulose to Glucose
• BACTERIA in SOIL-eaten by grazing animals that can
also be a source of biodegradation of dead plants
• In humans, cellulose acts as a DIETARY FIBER that
provides bulk to the digestive tract which helps move the
food to facilitate defacation.
PROJECTION
AND
HAWORTH
Fischer Projection
• The Fischer projection was devised by German
chemist Emil Fischer in 1891, who was the winner of
the Nobel Prize in Chemistry in 1902.
• In a Fischer projection the carbohydrate is shown in its
open chain form, rather than a cyclical one.
• Carbon atoms in the main chain of the carbohydrate
molecule are connected vertically, whilst hydrogen atoms
and hydroxyl groups are bonded horizontally.
• Carbohydrates are polyhydroxy compounds
• Chirality
• Aldose/ Ketose
• High-fiber food may also play a role in weight loss and
weight control
•Some dietary fibers nind lipid such as cholesterol and carry
them out of the body with feces.
• Lowers blood lipid concentration and decrease the risk of
heart attack and arterial disease
• 25-35 grams of dietary fibers daily are desirable.
B.
Chitin
• Linear polymer b(1,4) glycosidic linkage
• A polysaccharide that is similar to cellulose in both
function and structure
• Gives rigidity to the exoskeleton of crabs, lobsters,
shrimps, insects and other arthropods
• Occurs in the cell walls of fungi
A.
Aldehyde
Hyaluronic Acid
• Alternating pattern of glycosidic bonds in B(1,3) and
B(1,4)
• Acidic Polysaccharide
• Polysaccharide with a disaccharide repeating unit in
which one of the disaccharide components is an amino
sugar and one or both disaccharide components have
negative charge to a sulfate group or a carbonyl group
• Heteropolysaccharides
• Example: Hyaluronic Acid and Heparin
• Contains residues of N-acetyl-B- D-glucosamine and Dglucuronic acid
• Almost 50,000 disaccharide units per chain
• Used as lubricants in fluid and joints, associated in jellylike consistency of vitreous humor of the eye.
B.
Ketone
D and L Isomers

The Penultimate carbon- second to the last carbon LLeft; D-Right
Heparin
-6-
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
B.
STEREOCHEMISTRY
• the branch of chemistry concerned with the threedimensional arrangement of atoms and molecules and the
effect of this on chemical reactions.
• Optical Isomers
• Enantiomers- pairs of compounds with exactly the same
connectivity but opposite three-dimensional shapes.
Enantiomers are not the same as each other; one
enantiomer cannot be superimposed on the other.
Enantiomers are mirror images of each other.; All are
inverted
• Diastereomers- non-mirror image,
stereoisomers.; Some are inverted
Haworth Projection
• The Haworth Projection is a convenient notation for
showing the structure of sugars.
• Since every substituent points either straight up or straight
down, it is much easier to spot differences in configuration
between sugars in a Haworth than in a chair conformation.
• The only thing to keep in mind is that sugars are not flat
hexagons or pentagons and the Haworth is not meant to
show their 3-D shape.
non-identical
• Epimers- specifies one of a pair of stereoisomers. At
the stereogenic centre, two isomers present in the
molecule differ, while the rest remains identical.
-7-
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
Use of carbohydrates
• Energy
• Structural
• Signals
• Pharmaceutic
• Pharmacologic
• Presence in other biomolecules
Glycolipids and Glycoproteins: Cell Recognition
• Glycolipid- lipid molecule that has one or more
carbohydrate derivative that are covalently bonded.
• Glycoproteins-protein molecule that has one or more
carbohydrate units covalently bonded.
Dietary Considerations and Carbohydrates
• Foods high in Carbohydrate content constitute over
50% of diet of most people of the world
• Simple –dietary monosaccharide and disaccharide
• Sweet-tasting and are commonly referred to as
sugars
• Natural sugar and refine sugars
• Natural-sugarfoundinfoods(milk and fresh
fruit)contains calories
• Refined sugar-processed(sugars in sugar
beets and sugar cane)-empty calories
• Complex –polysaccharide
• Starch and are not too sweet
• Sources:grain,starch,protein, vitamins and
minerals
-8-
@alec_s
UNIVERSITY Of LA SALETTE, INC
SUBJECT: Pharmaceutical Biochemistry
CARBOHYDRATES
ADAPTED FROM: POWERPOINT/LECTURE
-9-
@alec_s