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CarbohydratesBIOCHEM2-converted (١)

The document provides an overview of carbohydrates, detailing their classification into monosaccharides, disaccharides, and polysaccharides, along with their roles in energy storage, structural support, and intercellular communication. It explains the formation of glycosidic bonds, the distinction between reducing and non-reducing sugars, and the various types of polysaccharides, including starch, glycogen, and cellulose. Additionally, it highlights the importance of enantiomers and epimers in biological systems.

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11 views28 pages

CarbohydratesBIOCHEM2-converted (١)

The document provides an overview of carbohydrates, detailing their classification into monosaccharides, disaccharides, and polysaccharides, along with their roles in energy storage, structural support, and intercellular communication. It explains the formation of glycosidic bonds, the distinction between reducing and non-reducing sugars, and the various types of polysaccharides, including starch, glycogen, and cellulose. Additionally, it highlights the importance of enantiomers and epimers in biological systems.

Uploaded by

zbm6mhpvfn
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BIOCHEMISTRY

Carbohydrates
Lecture 2
Carbohydrates
• Sugars ( Hydrate of Carbon) , formed from CO2 and H2O
• the most abundant organic molecules in nature
• the empiric/generic formula is (CH2O)n, where n >=3.
• ROLES:
✓Energy.

✓Mediating intercellular communication.

✓Structural support (e.g., cell walls)


Classification
• Monosaccharides=simple sugars

• Small polymers of sugars can be called:


• Disaccharides
• Trisaccharides
• Oligosaccharides (3-12 mono-)

• Large polymers of sugars: Polysaccharides (more than 12 mono-)


1-Monosaccharides
• Contain different numbers of carbon atoms and may be aldose or
ketoses with multiple enantiomer and epimeric forms.
• monosaccharide made from Aldehydes form Aldoses.
• Monosaccharide contain ketone called Ketose.
• Glyceraldehyde is the simplest aldose.
• Dihydroxyacetone is the simplest Ketone.
Configurationally
Isomers

❑Enantiomers in organic
chemistry (Mirror Image)
❑ L = Levorotatory
❑ D = Dextrorotatory

• (D- ana L- ) are NOT THE


SAME in biological systems.
• Most carbohydrates are
CHIRAL.
• Most sugar in nature have
the D configuration.
Enantiomers
Rules for Designation D and L Notation
1-Draw aldehyde or Ketone group at the top
2-Identify Lowest chiral center in the molecule
If –OH is on the right, then D If –OH is on the lift, then L
Recall !!
Despite enantiomers behave identically in a strictly chemical sense, they
are not biologically equivalent!!

Biological Systems can distinguish D and L sugars.


Epimers

Definition: Sugars that differs


from other only by the
configuration around one atoms.
(one chiral carbon.
e.g.,
Glucose and Mannose are
epimers with respect to C2
mono
We designation of a monosaccharide based on the
number of carbon atoms in the molecule and
functional group.

# of carbon Aldose Ketose


atoms
3 aldotriose ketotriose

4 aldotetrose ketotetrose

5 aldotpentose ketopentose

6 aldohexose ketohexose
Cyclical Sugars
❖ The hydroxyl group at C-5 reacts with
the carbonyl group at C-1 to produce
either of the two cyclic forms
a-D-glucose
b-D-glucose
• via the formation of a cyclic
intramolecular hemiacetal.

• These cyclic forms are enantiomeric


pairs due to the fact that a new chiral
carbon is created at C-1 in the
cyclization process.
Pyranose is the six-membered cyclic
hemiacetal formed from aldohexoses.
(-OH group at C5 to the C1 carbonyl group)
Furanose is the five-membered cyclic
hemiacetal formed by the ketohexose
fructose.
(-OH group at C5 to the C2 carbonyl group)
OR (-OH group at C6 to the C2 carbonyl
group)

✓ Glucose exists in aqueous solution


primarily as the six-membered
pyranose.
✓ a-D-Glucose is most prevalent in
biochemistry.
2- DISACCHARIDES
• Monosaccharides can be linked by glycosidic bonds in various
arrangements.
• The process of forming a disaccharide from two monosaccharides is
called a dehydration reaction or condensation reaction.
• Hydrolysis is the broken down of a disaccharide into
their monosaccharide components via enzymes, a water molecule is
added.
• Glycosidic bonds are cleaved by enzymes known as glycosidases.
• Lactose and sucrose are disaccharides that are used as metabolic fuel.
Lactose Structure
• Lactose has a B(1-4) glycolsidic bond.
• Consist of B-galactose and a-glucose.
• Lactose is a milk sugar.
• Digested by the enzyme called Lactase.
Maltose structure

• Malt sugar
• It is a product of starch ( amylose)
cleavage when beta-amylase breaks
it down.
• is a disaccharide formed from two
units of glucose joined with an
α(1→4) bond.
• Like glucose, maltose is a reducing
sugar.
Sucrose
▪ Is the most common sugar in nature.
▪ It is a disaccharide, a molecule
composed of
two monosaccharides: glucose and fru
ctose.
▪ Sucrose is produced naturally in
plants, from which table sugar is
refined.
▪ the monomers glucose and fructose
are linked via an ether bond between
C1 on the glucosyl subunit and C2 on
the fructosyl unit.
▪ it is classified as a non-reducing sugar.
Reducing sugar
• Is any sugar that is capable of acting as
a reducing agent because it has a
free aldehyde group or a
free ketone group.

• Reducing disaccharides
like lactose and maltose have only one of
their two anomeric carbons involved in
the glycosidic bond.
• All monosaccharides are reducing sugars.
Polysaccharides
• are complex biomacromolecules that are made up
chains of monosaccharides.
• The bonds that form these chains are glycosidic
bonds.
• Commonly found monomer units in
polysaccharides are glucose, fructose, mannose
and galactose which are simple sugars.
• Polysaccharides can be broadly classified into two
classes:
• Homo-polysaccharides – are made up of one
type of monosaccharide units. ex: cellulose,
starch, glycogen.

• Hetero-polysaccharides – are made up of two


or more types of monosaccharide units. ex.
hyaluronic acid and they provide extracellular
support for organisms.
Functions of Polysaccharides

•Storage polysaccharides: Polysaccharides such as starch and glycogen are called storage
polysaccharides because they are stored in the liver and muscles to be converted to energy later
for body functions. Starch is found in plants whereas glycogen is found in animals.

•Structural polysaccharides: Polysaccharides such as cellulose are structural polysaccharides


which are found in the cell walls of plants. Another structural polysaccharide is chitin.
Starch:

• It is the storage polysaccharide


found in plant cells.
• Exists in two forms:
✓ amylose is the helical form
of starch comprised only of
alpha-1,4 linkages.

✓ amylopectin that has a


structure like glycogen
except that the branched
alpha-1,6 linkages are
present on only about one
in 30 monomers.
Glycogen
➢ This polysaccharide is the
polysaccharide found in animals to
store energy.
➢ composed of alpha-1,4-glycosidic
bonds with branched alpha-1,6
bonds present at about every tenth
monomer.
➢ It is mainly produced by the liver
and muscles, but it can also be
made during a process
called glycogenesis.
Cellulose
• Is a structural polysaccharide that
is found in the cell wall of plants.
• It acts as a dietary fibre.
• Cellulose is said to be the most
abundant organic molecule on
earth. Wood, paper, and cotton are
common forms of cellulose.
starch

Glycogen

Cellulose
Heteropolysaccharides

• Hyaluronic Acid: Acts as a lubricant in the synovial fluid of joints


• Chondroitin Sulfate: It contributes to tensile strength and elasticity of
cartilages, tendons, ligaments, and walls of the aorta.
• Dermatan sulfate: It is found mainly in the skin, and also is in vessels,
heart, lungs. It may be related to coagulation and vascular diseases
and other conditions.
• Keratan sulfate: Present in the cornea, cartilage bone and a variety of
other structures as nails and hair.
• Heparin: Is present as an anticoagulant in the blood.
summary

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