Structure of Carbohydrates

Dr Imran Siddiqui (MBBS, MPhil)

College of Medicine
King Saud Bin Abdulaziz University for Health
Sciences
 PRETEST
1- What are Carbohydrates?

2- What are the significance of Carbohydrates?

3- How can you classify Carbohydrates?

 Definition
• Composed of the elements C, H and O and
empiric formula is C(H2O)n
• They are polyhydric alcohols with a carbonyl
group which may be an aldehyde or a ketone.
• Also called hydrates of carbon OR
saccharides, which means “sugars”
 Significance of carbohydrates
• Most abundant organic compound in nature
• A major source of energy from our diet
• Storage form of energy in plants and
animals
• Cell membrane component
• Structural component of many organisms
• The brain can only be fueled by
carbohydrate
 Types of Carbohydrates
 Monosaccharides are the simplest carbohydrates
 Empirical formula = CH2O

 Disaccharides consist of two monosaccharides

 Polysaccharides contain many monosaccharides
Some Monosaccharides
2 2
| |
The two simplest sugars

1—C—3 3—C—1
| |
4 4

Hence:
Note
Note
Want
Numerous
“Carbo”
Basic
Want to
to see
Formula:
(C)
see Chiral
that
“Hydrate”
that again?
Carbons
(CH2O)
again? (Hn 2O)
 The Glycosidic Bond
• Glycosidic bond - The bond between the
anomeric carbon of a carbohydrate and
some other group or molecule; the C-O in
disaccharides and the C-N in nucleosides
are two examples. glycosidic link.
• Note: The glycosidic bond involves only
the anomeric carbon.
• Formation of Glycosidic Bond
Disaccharide Synthesis
 Isomerism & Epimerism

• Isomerism: compounds that

have the same chemical
formula but have different
structures O H O H
C
• Epimers: two C
H C OH H C OH
monosaccharides differ in HO C H HO C H
configuration around only one H C OH HO C H
specific carbon atom other H C OH H C OH
than carbonyl group e.g. H C OH H C OH
H H
glucose and galactose are C4
epimer
Glucose Galactose
 D and L Notations
• 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
 α and β Anomers for D-
Glucose
• Anomers are isomers which differ in placement of
hydroxyl on C1
• The –OH is drawn down for the α -anomer, and
up for the β -anomer
CH2OH CH2OH
O O
β
OH
OH OH
OH OH OH
OH α OH

α -D-Glucose β -D-Glucose
 Sugars Can Be Reducing
Agents
• Reducing Sugars - A sugar that will reduce
inorganic ions such as Cu++ (Fehling’s reagent).

• All monosaccharides whether an aldose or a

ketose are reducing sugars.

• Most disaccharides are reducing sugars;

sucrose is a notable exception.
Fehling’s reaction to determine glucose levels in blood.

D-Glucose D-Gluconate

Currently glucose oxidase reaction (H2O2) is used to

determine blood glucose levels for diagnosis of diabetes.
Starch/Glycogen
 Quiz
1- Give various definitions of carbohydrates.
2- What is Glycosidic Bond?
3- What are Chiral Carbons?
4- What is hydrolysis?
5- What are Epimers?
6- What are D & L sugars
7- What is Anomeric Carbon
8- What are α & β sugars?