Biochemistry I

(SGS 236)
Carbohydrate Chemistry

Biochemistry I
Lecture 2
Dr. Ahmed Maher
Objectives
By the end of the lecture students should be
able to:
• Differentiate homoPolysaccharides from
heteroPolysaccharides.
• Describe different types of
homoPolysaccharides.
• Identify the classes and functions of GAGs.
• Know digestive enzymes and their location
• Describe the different types of sugar ttansport
across the cell membrane
Outline
• Polysaccharides
• Homopolysaccharides
• Heteropolysaccharides
• Digestion and Absorption
Polysaccharides
• Polysaccharides are formed of more than 9
monosaccharides.
• Polysaccharides are non-reducing since the
condensation involves the carbonyl groups
leaving only one free carbonyl group at the
end of the chain.
• They form colloidal solutions in water.
Polysaccharides
• Polysaccharides are classified to:
– HomoPolysaccharides (Simple carbohydrates)
– HeteroPolysaccharides (Mixed carbohydrates)
1. HomoPolysaccharides
• They are formed of one type of sugar units.
• Glucans: formed of D-glucose units.
• Examples :
➢ Starch
➢ Dextrin
➢ Glycogen
➢ Cellulose
• Fructans: formed of fructose units.
• Galactans: formed of galactose units.
• Pentosans: formed of pentose units.
1. HomoPolysaccharides: Starch
• It is formed of α-D-glucose units linked by glycosidic
linkage.
• It is the major source of stored carbohydrates in plants.
• It is formed of amylose and amylopectin.
Amylose:
• Unbranched starch molecule of 200 to 20,000 glucose
units linked together by α-1,4 glycosidic linkage.
1. HomoPolysaccharides: Starch
Amylopectin:
• Branched starch molecule of up to 2 millions glucose
units linked together by α-1,4 glycosidic linkage.
• Branches are formed of chains of glucose attached
to the main chain by α-1,6 glycosidic linkage at the
branch points.
1. HomoPolysaccharides: Glycogen
• Its structure is highly branched homopolysaccharide.
• Each branch contains 8-12 α-D-glucose units linked by α-
1,4 glycosidic linkage.
• At branching point glucose units are attached to the main
chain by α-1,6 glycosidic linkage.
1. HomoPolysaccharides: Glycogen

• It is the major form of stored carbohydrates in

animals.
• Glycogen is stored in liver and skeletal muscles.
• It represents 10% of the net weight of liver but
only 1-2% of skeletal muscles net weight.
• In humans total muscle glycogen is around 4
times of the liver glycogen.
1- HomoPolysaccharides: Glycogen vs.
Amylopectin
Glycogen Amylopectin
Present in animals. Present in plants.
Larger number of branches (highly Lower number of branches
branched) (branched)
Shorter branches Longer branches
1. HomoPolysaccharides: Dextrins
• Dextrins are the products of the hydrolysis of starch
by amylase enzyme with maltose units being
liberated.
• First higher dextrins are produced, amylase further
hydrolyzes higher dextrins to produce intermediate
dextrins then lower dextrins.
• Starch amylase Dextrins + Maltose
1. HomoPolysaccharides: Dextrins
• Iodine solution can be used to differentiate
between different dextrins.

Observation with
iodine
Starch Blue colour
Higher dextrins Violet colour
Intermediate dextrins Red colour
Lower dextrins No colour
1. HomoPolysaccharides: Cellulose
• It is present in cell walls of plants aw well as in plant
fibers.
• It is an unbranched chain formed of 300 to 1500 β-D-
glucose units linked together via β-1,4 glycosidic linkages.
• Humans cannot digest cellulose.
• However the presence of cellulose in diet is important
because it increases the bulk of food which stimulates
intestinal contractions and prevents constipation.

Cellulose
Glucose Amino Glycans
GAGs
Presented by:
Basma Mohamed Gaber 201723
Merola Adel 204497
Jessica Halim 200627
Dina Magdy 201411
Mohamed Abou Hamar 204497
Antony Mena 200715
 Carbohydrates

Polysaccharide
Monosaccharide

Disaccharide Oligosaccharide
 Polysaccharide

Homopolysaccharide
Heteropolysaccharide
Heteropolysaccharides:
Mixed polysaccharide formed of more than one type of simple sugar unit.

heteropolysaccharides can be differentiated into two classes :

1) non nitrogenous molecules as the agar found in coral reef

2) nitrogenous molecules as GAGs which are most abundant in animal cells

General characteristics of GAGs
▪ GAGs are large, unbranched complexes, -vely charged
heteropolysaccharide chains.

▪ Also known as mucopolysaccharide

▪ GAGs are associated with small amount of protein forming the

proteoglycans which consists of 95% of carbohydrates.

▪ GAGs bind with water producing a gel like matrix that forms the ground
substance of the extracellular matrix of cell.
Structure of GAGs
1- Amino sugar as N-acetylglucosamine
Bond
(it either be sulphated or acetylated) Unit
2-sugar acid as glucuronate and iduronate

Bond Bond
Unit ____ Unit ___ Unit GAG
_ s
Classification of GAGs:

GAGs

Non-Sulfated Sulfated
● Chondroitin Sulfate
● Hyaluronic acid ● Keratan Sulfate
● Dermatan Sulfate
● Heparin
● Heparan sulfate
1) Hyaluronic Acid
Chemical formula: (C14H21NO11)n

(D-glucuronic acid + N-acetyl-D-glucosamine).

Functions:
-Lubricant & Shock absorber (synovial fluid in joints)

-Key role in tissue regeneration -Inflammation response

Site: Skin, Joints, Eyes, cartilage, umbilical cord & loose C.T.

Note: Largest amount found in skin, connective tissue and eye

2) Chondroitin sulfate
Chemical formula: C13H21NO15S & C28H42N2O28S2

(D-glucuronic acid + N-acetyl-D-galactosamine 4-sulfate, or 6-sulfate).

Function:

-Important role in elasticity -Main component of all cartilage

-Natural substance used in treatment of Osteoarthritic

Site: Aorta, Tendons, cartilage(compressibility) and ligaments

Note: The most abundant GAG in body is Chondroitin sulfate

3) Keratan sulfate
Chemical formula: C28H48N2O32S4

(D-galactose + N-acetyl-D-glucosamine-6-sulfate).

Function: -Important role of corneal development

-maintenance of transparency of cornea tissue

Site: Cornea of the eye

4) Dermatan sulfate
Chemical formula: C14H21NO15S

(L-iduronic acid + N-acetyl-D-galactosamine-4- sulfate).

Function: -Has key role in constituent of tissues and

-wound repair

-regulation of blood coagulation

-response to infection

Site: The most GAG found in skin, arterial smooth muscles, and heart valves
5) Heparin
Chemical formula: C12H19NO20S3

(L-iduronic acid, or D-glucuronic acid-2-sulfate + D-glucosamine-2,6-

bisulfate).

Function: -Decrease clotting ability -Prevent harmful clots formation in

blood vessels (anticoagulant)

Site: Line arteries

Note: It is formed by mast cells

6)Heparan sulfate
Chemical formula: (C26H40N2O36S5)n

Function:

-Play important role in recruitment, rolling and firm adhesion of leukocytes

to activated endothelium

-Help reduce capillary permeability to the negatively charged plasma protein

(by its negative charges)

Site: Found in basement membrane of blood capillaries &vessels where

negative charges help reduce capillary permeability to the negatively
charged plasma proteins.
Properties and functions of GAGs :

1. Gel like matrix:

● GAGs are polyanionic (several negative charges) due to carboxylic and sulfate groups.
● Molecules bind to water and form gel-like matrix.
● Its function is to support cellular and fibrous components of connective tissues.

2. Slippery consistency:
● Due to several negative charges GAGs molecules repel each others leading to slippery
consistency.
● Its function is to produce slippery consistency of mucous as well as lubricating property
of synovial fluid.
Properties and functions of GAGs :

3. It has shock absorbing properties:

● Because GAGs bind to large amounts of water, when
the GAGs are compressed water squeezes out and
GAGs occupy smaller volume.
● When compression is released GAGs are hydrated
and regain original volume.
● Its function is the resilience of synovial fluid and
vitreous humor of the eye.
4. It play a crucial role in cell signaling process
including regulation of cell growth and wound
repair.
References
https://www.mayoclinic.org/

https://www.sciencedirect.com

https://pubchem.ncbi.nlm.nih.gov/

https://academic.oup.com/

https://www.news-medical.net/life-sciences/Structure-and-Function-of-
Proteoglycans.aspx#5

https://onlinelibrary.wiley.com/doi/full/10.1111/j.1747-0285.2008.00741.x
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