STEREOCHEMISTRY

OF CARBOHYDRATES

 HASEEB AKRAM 265

 IBSHAM AKBAR 293
 HASSAN SARDAR 289
 TALHA ISHAQ 305 MAM RABIA HUSSAIN
 SHEHRYAR 316
 MUHAMMAD UMER 310
 AFFAN 308
 NUMAN 244
 STEREOCHEMISTRY
The branch of chemistry that deals with
the three dimensional arrangement of
atoms and molecules and the effect of
this arrangement on chemical reactions.
WHY WE NEED TO STUDY STEREOCHEMISTRY OF CARBOHYDRATES
Biological molecules may react at different rate with the two enantiomers.
A certain bacterium or medicine may digest one enantiomer but not the other.
Example:
Pig liver esterase (PLE is a widely used enzyme for asymmetric ester hydrolysis) used
for the selective cleavage of one enantiomer ester.
 STEREOISOMERISM

It is a form of isomerism in which molecules have the same molecular

formula and sequence of bonded atom, but differ in the three
dimensional-orientation of their atoms in space.
Example:
Glyceraldehyde, the simplest carbohydrate
exists in two isomeric forms that are mirror
images of each other.
 CHIRAL MOLECULE

 Chiral molecules have the same relationship to each other that your left and right hand
when reflected in mirror.
Achiral objects can be superimposed on the mirror images. For example, drinking glasses,
spheres, and cubes.
If any of the two groups on the carbon are the same, the carbon atom cannot be chiral.
Many organic compounds, including carbohydrates, contain more then one chiral molecule.
EXAMPLE
Identify the chiral carbon atom (if any) in each of the following molecules:
 FISCHER PROJECTION
It is devised by Emil Fischer in 1891.
It is used for the representation of two dimensional representation of
a three dimensional organic molecule.
Uses:
Fisher projection is mostly used to represent CHO.
It is also used for amino acids or for other molecules.
Example:
Representation of glucose by fisher projection.
NAMING STERIOISOMERS
When there is more then one chiral center in a carbohydrate then follow three steps for
naming:
Look at the chiral carbon farthest from the carbonyl group.
If the hydroxyl group points to right ,it is D-Isomer.
If the hydroxyl group points to left, it is L-isomer.
HAWORTH PROJECTION

It is a common way of writing a structural formula to represent the

cyclic structure of monosaccharides with a simple three-dimensional
perspective.
Carbon 1 is also known as anomeric carbon.
In carbon 1 we have to identify anomers.
 Anomers alpha (α), and beta (β).
SPECIALITY OF CHIRAL
MOLECULES
Molecules which are enantiomers of each other have exactly the same
physical properties:
 Melting point, boiling point, index of refraction, etc but not their
interaction with polarized light.
Polarized light vibrates only in one plane; it results from passing
light through a polarizing filter.
OPTICAL ACTIVITY
 A levorotatory (–) substance rotates polarized light to the left.
 [E.g., glucose; (-)-glucose]
 A dextrorotatory (+) substance rotates polarized light to the right.
[E.g., d-glucose; (+)-glucose]
 Molecules which rotate the plane of
 polarized light are optically active.
THANK YOU