BME 102: LECTURE 4

Background INTRODUCTION

➢ Fruits, vegetable, beans, and grains are all sources of carbohydrates. They are the
simple and complex sugars obtained from the foods we eat. Not all carbohydrates are
the same.
➢ Carbohydrates are one of the most important biomolecules essential for various cellular
processes. These organic compounds are made up of Carbon, Hydrogen, and
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Oxygen atoms. Based on their structure, they come in various forms, from simple
sugars to complex polysaccharides.
Background INTRODUCTION

➢ The word "carbohydrate" comes from the

Greek word sakharon, which means
"sugar".
➢ Simple carbohydrates include sugars such as
table sugar or sucrose and fruit sugar or
fructose. Complex carbohydrates are
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composed of several simple sugars linked
together and include starches and fiber.
➢ Carbohydrates are an important part of a
healthy diet and a valuable energy source
needed to perform normal biological
activities.
Background TYPES OF Carbohydrate

Carbohydrates are one of the four major

classes of organic compounds in
living cells. They are produced
during photosynthesis and are the main
sources of energy for plants and animals.
The term carbohydrate is used when
referring to a saccharide or sugar and its
derivatives. Carbohydrates can be simple
sugars or monosaccharides, double sugars
or disaccharides, composed of a few Linear Discriminant Analysis
sugars or oligosaccharides, or composed
of many sugars or polysaccharides.
 CARBOHYDRAT
ES

SIMPLE COMPLEX

POLYSACCHARIDE
DISACCHARIDE – OLIGOSACCHARIDE –
MONOSACCHARIDE – – STARCH,
MALTOSE,
GLUCOSE, RAFFINOSE
SUCROSE, GLYCOGEN,
FRUCTOSE, LACTOSE STACHYOSE
CELLULOSE,
GALACTOSE
DEXTRIN
 CHO TYPES OF Carbohydrate

All carbohydrates contain the same three elements,

whether the carbohydrates are simple sugars,
starches, or other polymers. These elements are:
▪ Carbon (C)
▪ Hydrogen (H)
▪ Oxygen (O)
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sugar sugar sugar sugar sugar sugar sugar sugar

CH2O EXAMPLE OF carbohydrates

Monosaccharides: glucose, fructose, galactose

Disaccharides: sucrose, lactose
Polysaccharides: chitin, cellulose
 CH2O Monosaccharides (CH2O)n

A monosaccharide or simple sugar has a formula that is some multiple of CH2O. For instance, glucose (the
most common monosaccharide) has a formula of C6H12O6. Glucose is typical of the structure of
monosaccharides. Hydroxyl groups (-OH) are attached to all carbons except one. The carbon without an
attached hydroxyl group is double-bonded to an oxygen to form what is known as a carbonyl group.
 CH2O Monosaccharides (CH2O)n

❖ Aldose - monosaccharide in which the carbonyl group is an aldehyde

❖ Ketone - monosaccharide in which the carbonyl group is a ketone
❖ Triose - monosaccharide with 3 carbon atoms
❖ Aldohexose - 6-carbon aldehyde (e.g., glucose)
❖ Aldopentose - 5-carbon aldehyde (e.g., ribose)
❖ Ketohexose - 6-carbon hexose (e.g., fructose)
 MONOSACCHARIDES

BASED ON No OF C ATOMS BASED ON

FNCTIONAL GROUP

✓ TRIOSES (C3H6O3) –GLYCERALDEHYDE, ALDOSE-GLECEALDEHYDE,

DIHYDROXYACETONE GLUCOSE

✓ TETROSE (C4H8O4) – ERYTHROSE,

THREOSE

✓ PENTOSE (C5H10O5) – RIBULOSE,

ARABINOSE

✓ HEXOSES (C6H12O6) – GLUCOSE, KETOSE –DIHYDROXYACETONE

DIHYDROXYACETONE,
FRUCTOSE, FRUCTOSE
GALACTOSE

✓ HEPTOSES (C7H14O7) – GLUCOHEPTOSE

SO ON………
CH2O

No of Carbon atom Name examples

3 Triose Glyceraldehyde

4 Tetrose Erythrose and threose

5 Pentose
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Ribose and xylose

6 Hexose Glucose, fructose, mannose, and galactose

7 Heptose Sedoheptulose and mannoheptulose

 Monosaccharides may exist as
CH2O
straight-chain (acyclic)
molecules or as rings (cyclic).

.
 Fischer Projections

• Used to represent carbohydrates (chiral

carbons)
• Places the most oxidized group at the top
(C1)
• Uses horizontal lines for bonds that come
forward
• Uses vertical lines for bonds that go back
 D and L Notations

Stereochemistry
Monosaccharides exhibit stereochemistry. Each simple sugar can be in either D- (dextro) or L- (levo) form. The D-
and L- forms are mirror images of each other. Natural monosaccharides are in the D- form, while
synthetically produced monosaccharides are usually in the L-form.

• By convention, the letter L is assigned to the structure with the —OH on the
left
• The letter D is assigned to the structure with —OH on the right
D and L Monosaccharides
• Most monosaccharides found in living organisms
are D

D
D L
 CH2O
Pentose Sugar
Aldopentoses Ketopentoses
Aldopentoses are a type of Ketopentoses are another type of
pentose sugar that contains an pentose sugar that contains a
aldehyde group (-CHO) on one ketone group (C=O) on one of the
of its carbon atoms. Ribose, carbon atoms. One example of
found in RNA, and deoxyribose, ketopentose is ribulose, a vital sugar
found in DNA, are examples of involved in the Calvin cycle, a
aldopentoses. Ribose contains process in photosynthesis. Xylulose
the aldehyde group and is a is another important ketopentose. It
typical aldopentose in RNA. Linear Discriminant
participates Analysis
in various metabolic
Deoxyribose is also an pathways, including glycolysis and
aldopentose, derived from the pentose phosphate pathway,
ribose but lacking one oxygen contributing to energy generation
atom. and other essential biochemical
processes.
The two types of pentose sugars in nucleotides are:
1.Ribose is a pentose sugar that is a component of RNA. It forms the backbone of the RNA molecule. Ribose
can exist as L-ribose and D-ribose enantiomers. L-ribose is unstable in biological systems. So, living
organisms primarily use D-ribose. D-ribose is the biologically functional form of ribose and is commonly
found in nucleic acids, ATP, and other essential biomolecules.
2.Deoxyribose is a modified form of ribose. It lacks one oxygen atom, which is removed from the second
carbon in the carbon chain. Deoxyribose is a component of DNA that forms the backbone of the DNA
molecule. It also exists in two optical isomeric forms: D-deoxyribose and L-deoxyribose.
 CH2O
DISACCHARIDE
Two monosaccharides joined together by a
glycosidic linkage is called a double sugar
or disaccharide.

The process of linking monosaccharides

together with one another through
glycosidic bonds and release of water is
known as condensation
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The reverse process is known as hydrolysis
( adding water to disaccharides).
CH2O
DISACCHARIDE

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Maltose Also known as malt sugar. It is found in germinating grain
(such as barley), and is formed during the hydrolysis of starch to glucose
during digestion
The condensation of beta galactose and beta glucose
through beta 1 to 4 glycosidic linkage yield Lactose
Also known as milk sugar. Lactose constitutes 5% of
cow's milk and 7% of human milk. It is digested by
the enzyme lactase.
Sucrose Also known as table sugar. Both anomeric carbons of glucose and fructose are tied together in
the glycosidic linkage (⍺-1-2 or ⍺-1, β-2 glycosidic bond). Sucrose is abundant in sugar cane and
sugar beets; maple syrup contains about 65% sucrose, with glucose and fructose present as well;
caramel is the solid residue formed from heating sucrose. A flavoring agent called invert sugar is
produced by the hydrolysis of sucrose under acidic conditions, which breaks it apart into glucose and
fructose; invert sugar is sweeter than sucrose because of the fructose. Some of the sugar found in
honey is formed in this fashion; invert sugar is also produced in jams and jellies prepared from acid-
containing fruits. Sucrose is commonly used by plants to transport glucose from one part of the plant to
another.
 CH2O

Sucrose (saccharose): glucose + fructose

Sucrose is table sugar. It is purified from sugar cane or sugar beets.
Maltose: glucose + glucose
Maltose is a sugar found in some cereals and candies.
Lactose: galactose + glucose
Lactose is a disaccharide found in milk. It has the formula C12H22O11 and is
an isomer of sucrose.
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Lactulose: galactose + fructose
Lactulose is a synthetic (man-made) sugar that is not absorbed by the body
but is broken down in the colon into products that absorb water. Its primary
use is to treat constipation.
CH2O

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CH2O
DISACCHARIDES

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 CH20
OLIGOSACCHARIDE
• An oligosaccharide consists of a small number of monosaccharide units (from 3 to 10)
joined together. Oligosaccharides are found in cell membranes and assist other membrane
structures called glycolipids in cell recognition.

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Raffinose an oligosaccharide found in peas and beans; largely undigested

until reaching the intestinal flora in the large intestine, releasing hydrogen,
carbon dioxide, and methane
 CH20
POLYSACCHARIDE
• Polysaccharides (aka Glycans) can be composed of hundreds to thousands of
monosaccharides combined together. These monosaccharides are joined together through
dehydration synthesis.
• By convention, a polysaccharide consists of more than ten monosaccharide units, while an
oligosaccharide consists of three to ten linked monosaccharides
• The general chemical formula for a polysaccharide is Cx(H2O)y.
• Polysaccharides may be linear or branched. Linear polysaccharides can form rigid
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polymers, such as cellulose in trees. Branched forms are often soluble in water, such as gum
arabic.
 CH20
POLYSACCHARIDE STRUCTURE
• Polysaccharides form when monosaccharides or
disaccharides link together by glycosidic bonds. The
sugars participating in the bonds are called residues.
• The glycosidic bond is a bridge between the two
residues consisting of an oxygen atom between two
carbon rings.
• The glycosidic bond results from a dehydration
reaction (also termed a condensation reaction). In the
dehydration reaction a hydroxyl group is lost from a
carbon of one residue while a hydrogen is lost from a
hydroxyl group from another residue.
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• A water molecule (H2O) is removed and the carbon of
the first residue joins to the oxygen from the second
residue.
POLYSACCHARIDES

✓ KNOWN AS GLYCANS
✓ REPEATING MONOSACCHARIDE UNITS CONNECTED BY GLYCOSIDIC BONDS
✓ ALMOST INSOLUBLE
✓ NOT SWEET
✓ IDEAL STORAGE AND STRUCTURAL COMPONENTS
✓ 2 TYPES –
a) HOMOPOLYSACCHARIDES b) HETAROPOLYSACCHARIDES
( ONLY ONE TYPE OF MONOSACCHARIDE (CONDENSATION OF 2 OR MORE
TYPES
MONOMERS ) OF MONOSACCHARIDES)
STARCH, GLYCOGEN, CELLULOSE PEPTIDOGLYCAN, HYALURONIC
ACID,
AGAR, CHITIN
 CH20
POLYSACCHARIDE
• Polysaccharides have several functions
including structural support and storage.
Some examples of polysaccharides include
• Starch,
• Glycogen,
• Cellulose,
• Chitin. Linear Discriminant Analysis
 CH20 Starch
• Is a vital form of stored glucose in plants. Vegetables and grains are good sources of starch.
In animals, glucose is stored as glycogen in the liver and muscles. Branched starch is known
as amylopectin (contain 2 types of bonds alpha 1-4 and alpha 1-6 glycosidic bonds)
Unbranched starch are referred to amylose (contain 1 type of bonds alpha 1-4 glycosidic
bonds

Amylose. (a) Amylose is a linear chain of α-D-glucose units joined

together by α-1,4-glycosidic bonds. (b) Because of hydrogen bonding,
amylose acquires a spiral structure that contains six glucose units per
turn.
Pasta, Rice , Potatos
Bread
 GLYCOGEN
➢ CARBOHYDRATE RESERVE IN ANIMAL : ANIMAL STRACH
➢ HIGH CONCENTRATION IN LIVER, MUSCLE , BRAIN
➢ MADE UP OF GLUCOSE UNIT

Glycogen is a form of glucose, a main source of

energy that your body stores primarily in your
liver and muscles. Your body needs
carbohydrates from the food you eat to form
glucose and glycogen.
 CH20
Cellulose
• Is a fibrous carbohydrate polymer that forms the cell walls of plants. It composes about one-
third of all vegetable matter and cannot be digested by humans.

a) There is extensive hydrogen bonding in the structure of cellulose. (b)

In this electron micrograph of the cell wall of an alga, the wall consists
of successive layers of cellulose fibers in parallel arrangement.
CH20

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 CH20

Chitin
Is a tough polysaccharide that can be found in some species of fungi. Chitin also forms the
exoskeleton of arthropods such as spiders, crustaceans, and insects. Chitin helps to protect
the animal's soft internal body and helps to keep them from drying out.

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Schematic representation of (a) chitin and

(b) chitosan macromolecules
 CH20
HOMOPOLYSACCHARIDE VS. HETEROPOLYSACCHARIDE
• A homopolysaccharide or homoglycan
consists of one sugar or sugar
derivative. For example, cellulose,
starch, and glycogen are all composed
of glucose subunits. Chitin consists of
repeating subunits of N-acetyl-D-
glucosamine, which is a glucose
derivative.
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 CH20
HOMOPOLYSACCHARIDE VS. HETEROPOLYSACCHARIDE
•A heteropolysaccharide or
heteroglycan contains more than
one sugar or sugar derivative. In
practice, most
heteropolysaccharides consist of
two monosaccharides
(disaccharides). They are often
associated with proteins. A good
example of a heteropolysaccharide
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is hyaluronic acid

Hyaluronic acid consists of N-acetyl-D-glucosamine linked to glucuronic acid

 Why do we need carbohydrate?
CH20
FUNCTIONS OF POLYSACCHARIDE
• The three main functions of polysaccharides are:
• providing structural support,
• storing energy, and
• sending cellular communication signals.

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 CH20
Structural support
• Linear molecules, like cellulose and chitin, are strong and rigid. Cellulose is the primary
support molecule in plants, while fungi and insects rely on chitin.
 CH20
Storing energy
• Polysaccharides used for energy storage tend to be branched and folded upon themselves.
Because they are rich in hydrogen bonds, they are usually insoluble in water. Examples of
storage polysaccharides are starch in plants and glycogen in animals.
 CH20
Sending cellular communication signals
• Polysaccharides used for cellular communication are often covalently bonded to lipids or
proteins, forming glycoconjugates. The carbohydrate serves as a tag to help the signal reach
the proper target. Categories of glycoconjugates include glycoproteins, peptidoglycans,
glycosides, and glycolipids

Linear Discriminant Analysis

 CH20
CHEMICAL TEST
• A common chemical test for polysaccharides is the Periodic Acid-schiff (PAS) stain. Periodic
acid breaks the chemical bond between adjacent carbons not participating in a glycosidic
linkage, forming a pair of aldehyde. The Schiff reagent reacts with the aldehydes and yields
a magenta purple color. PAS staining is used to identify polysaccharides in tissues and
diagnose medical conditions that alter carbohydrates.

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CH2O DIGESTION

Carbohydrates in the foods we eat must

be digested to extract the stored energy.
As food travels through the digestive
system, it is broken down allowing
Motivations glucose to be absorbed into the blood.
Enzymes in the mouth, small intestines,
and pancreas help to break down
carbohydrates into their monosaccharide
constituents. These substances are then
absorbed into the bloodstream.
 CH2O DIGESTION

The circulatory system transports glucose in the blood to cells and tissues
of the body. The release of insulin by the pancreas allows glucose to be
taken in by our cells to be used to produce energy through cellular
respiration. Excess glucose is stored as glycogen in the liver and muscles
for later use. An overabundance of glucose can also be stored as fat in
Motivations
adipose tissue.

Digestible carbohydrates include sugars and starches. Carbohydrates that

cannot be digested include insoluble fiber. This dietary fiber is eliminated
from the body through the colon.
Background STUDY QUESTIONS QUESTIONS

What is the difference between

monosaccharides, disaccharides and
polysaccharides and list 3 example of each

Draw acyclic and cyclic structure of ribose

and glucose

What is the difference between

homopolysaccharide vs. Heteropolysaccharide
List 3 functions of polysaccharides
Background Homework: On the day of midterm

Draw an oligosaccharides with 9 units

connected by alpha 1-4 glycosidic linkages

Draw branched polysaccharides that contain 20

units (cyclic rings) connected by
Both alpha 1-4, 1-2 glycosidic bonds

or
Both beta 1-4, 1-2 glycosidic bonds