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U1 Isomerism 2017

The document outlines the chemistry of natural products, including their definitions, chemical structures, and classifications such as isomerism and stereochemistry. It covers various types of isomerism, including structural and stereoisomerism, and discusses the significance of chirality in natural products. Additionally, it emphasizes the importance of understanding these concepts for applications in pharmacy and drug utilization.

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0% found this document useful (0 votes)
19 views96 pages

U1 Isomerism 2017

The document outlines the chemistry of natural products, including their definitions, chemical structures, and classifications such as isomerism and stereochemistry. It covers various types of isomerism, including structural and stereoisomerism, and discusses the significance of chirality in natural products. Additionally, it emphasizes the importance of understanding these concepts for applications in pharmacy and drug utilization.

Uploaded by

t15122127
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
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Chemistry

Of
natural products

1
Course objectives

• Define natural products


• Describe chemical structure of Natural products
• Explain Chemical reactions
• List Some chemical classes
• Identify Related properties of natural products
and their application
• Counseling peoples about natural products
• Preserve d/nt sources of natural products
2
Chemistry of natural
products
Topic outline

• Introduction

• Stereochemistry
• Isomerism
• Enantiomers, diastreomers and meso cpds

• Significance of stereoisomerism

3
Introduction
Chemistry:
• Is a science that deals with the
composition and properties of
substances and various elementary
forms of matter.
• Chemistry is the science of the
composition, structure, properties
and reactions of matter, especially of
atomic and molecular systems.

4
Cont…

Pharmacy:
• Is a branch of the health sciences
dealing with the
• preparation,
• dispensing,
• proper utilization of drugs.

5
Natural products

• What are natural products?

6
Con…
• Natural products
• Are products are made by enzymes from various natural
sources, plants, microbes and animals.
• Natural products can be
• An entire organism, A part of an organism, An extract,
Pure compounds

7
1.1. Isomerism
• Isomerism (Greek isos, equal; meros, parts) is the
occurrence of two or more compounds that have the same
molecular formula but different physical, chemical and
biological characteristic due to structures and appearance
in space.

• The compounds are called isomers


Isomers of butene: 1-butene and 2-butene differ in the positions of
3 1 the double bond. 3 1
1- Butene 2- Butene
4 2 4 2

8
Isomerism cont.
• There are two main classes of isomerism

A Structural (constitutional) isomerism


a. Chain isomerism,
b. Positional isomerism
c. Functional isomerism
d. Metamerism
e. Tautomerism
f. Ring Chain isomerism
B Stereoisomerism
g. Conformational isomerism
h. Configurational isomerism
i. Geometric
ii. Optical (enantiomers, diastereomers)

9
10
Cont…
CHAIN
ISOMERISM

STRUCTURAL ISOMERISM POSITION ISOMERISM


Same molecular
formula but
FUNCTIONAL
different GROUP
ISOMERISM
structural
formulae
GEOMETRICAL
ISOMERISM
Occurs due to the
restricted rotation of C=C
STEREOISOMERISM
 Same molecular double bonds... two
forms… CIS and TRANS
formula but atoms
occupy different
OPTICAL ISOMERISM
positions in space.
Occurs when molecules
have a chiral centre. Get
two non-superimposable
mirror images.
11
1.1.1 Constitutional/structural/
isomersim

• Are compounds having the same molecular


formula but differ in the nature or
sequence of bonding , have different
IUPAC names, the same or different
functional groups
• Constitutional isomers generally have
different physical and chemical
properties.
12
O
a) OH
Ethanol C2H6O
Dimethylether

b)

Butane C4H10 Iso-


butane

Constitutional isomerism between


(a)-ethanol and dimethylether; and
(b) butane and iso-butane
13
Cont…

14
Chain/skeletal/: different arrangements of the carbon
skeleton, similar number of atoms and functional groups with
the same. chemical properties, slightly different physical
properties, more branching = lower boiling point

Sometimes more than one type of constitutional isomerism


occurs in the same molecule.
The more carbon atoms there are, the greater the number of
possible isomers

15
Positional: Different positions of side
chains, substituents, functional groups,
double bonds, triple bonds, etc. on the
parent chain

16
Functional Group: The existence of various
functional groups causes functional
isomerism. The functional isomers have the
same molecular formula but possess
different functional groups.

17
4. Metamerism: When various alkyl groups are
joined to the same functional group, metamerism
results. For example, the ether functional group is
present in the following metamers. However, the type of
alkyl groups that are joined to the oxygen atom in each
one makes a difference.

18
5. Tautomerism- The dynamic equilibrium between two
compounds having the same chemical formula is
referred to as tautomerism. The tautomers live in
dynamic equilibrium and have several functional groups.

19
6 Ring chain isomerism- Ring chain
isomers are substances with the same
chemical formula but an open chain and
cyclic structure. Ring chain isomers
include propene and cyclopropane, for
instance.

20
1.1.2 Stereoisomerism
• Stereochemistry is a science, in organic
chemistry, which deals with the chemistry
of molecules in three dimensions
(Greek: stereos, solid).
• A clear understanding of stereochemistry
is crucial for the study of complex
molecules that are biologically important,
e.g. proteins, carbohydrates and
nucleic acids, and also drug molecules,
especially in relation to their behavior and
pharmacological actions.

21
Stereochemistry
• Stereochemistry is the study of the static
and dynamic aspects of the three-
dimensional shapes of molecules

22
Stereoisomerism cont.
 Stereoisomers
• Are compounds made up of the same atoms
connected by the same sequence of
bonds, but having different three
dimensional structures
• There are two major types of stereoisomers:
i. Conformational isomers and
ii.Configurational isomers

23
HO HO

O
O HO
HO
HO
OH
HO HO
OH
OH

α-Glucose β-Glucose

OH

O OH

trans-Cinnamic acid cis- Cinnamic acid

Figure 1.3: Examples of Stereoisomers

24
1.1.2.1 Conformational isomers
• Atoms within a molecule move relative
to one another by rotation around
single bonds.
• Such rotation of covalent bonds gives
rise to different conformations of a
compound.
• Each structure is called a conformer or
conformational isomer.
• Generally, conformers rapidly
interconvert at room temperature.

25
• Stereoisomers which are interconvertible simply by
rotation of one part of the molecule with respect to other
about a single bond.
• Eclipsed conformation:
• C-H bond opposite to each other(minimum distance)
• Staggered conformation:
• C-H bonds at maximum distance

H H
H re
d H ed
St
a g g e
H E clip
s H
H H H H
H H
1.1.2.2 Configurational
isomers
• The actual arrangement or orientation (in
space) of atoms/groups attached to the
chiral carbon (stereogenic centre or
stereocentre) is called the configuration
of a compound.
• Configurational isomers differ from each
other only in the arrangement of their
atoms in space, and cannot be converted
from one into another by rotations about
single bonds within the molecules.

27
Configurational isomers cont.
• Configurational isomers: common
with C=C,C=N,N=N
• Geometric (cis-trans) isomers

• Optical (enantiomers, diastereomers)

28
Configurational isomers cont.

A. Chirality: handedness (Greek: chair,


hand)

• Chirality refers to the geometric property of a


rigid object (or spatial arrangement of points
or atoms) of being non-superimposable on its
mirror image.

• For example,
• Our left and right hands are mirror images of each other, and cannot
be superimposed on each
• Other chiral objects include shoes, gloves and printed pages 29
Cont…

30
Configurational isomers cont.
• Many compounds that occur in living
organisms, e.g. carbohydrates and
proteins, are chiral
• The most common feature in chiral
molecules
• Is a tetrahedral (i.e. sp3-hybridized)
• Asymmetric carbon.
• Do not have a plane of symmetry.

31
X X

W C Y W C Z

Z Z

(a) Chiral carbon


(b) Achiral carbon
Four different
At least two same
groups/atoms
groups/atoms (Z)
present
present

Cl Cl

H H (c) Achiral molecule


Br Br
H H Superimposable
mirror image
Mirror image

(a) Chiral carbon, (b) Achiral carbon and (c)Achiral


molecule 32
Configurational isomers cont.
• When there are two or more atoms/groups
that are the same, the carbon is called
achiral
• Achiral molecules often have a plane
of symmetry.
• Achiral molecules, the compound and
its mirror image are the same,
• If you rotate the mirror image through
180o, it is identical to the original
structure.

33
Configurational isomers cont.
B. The chiral center
• A Carbon atom to which four d/t groups are
attached is a chiral center.
• The maximum number of isomers that can exist is

Equal to 2n where n is the number of


chiral centers.
• Where meso compounds exist, there
will be fewer than this maximum
number plane of symmetry.
34
Classify each of the following pairs as chiral or
achiral.
CH3 CH3
A) D)
CH3 H3C
Cl Br Cl
Br

B) CH3 CH3

Br Br
Cl Cl H
H

C) H Br H
Br

F F

35
Are the following pairs of compounds
consitutional isomers or stereoisomers?

36
I. Geometrical isomers
• Exhibit by molecules having the same
stricture but differing in their configuration
due to molecular symmetry
• Geometrical isomerism is found in
alkenes and cyclic compounds.
• In alkenes, there is restricted rotation
about the double bond.
• When there are substituent groups attached to the double
bond, they can bond in different ways, resulting in
• Trans (opposite side) and cis (same
side) isomers
• These are called geometrical isomers.

37
Cont…
H
G
C C
H G
Cis Trans
Trans-Isomer
(i) Substituent G is on opposite sides
on the double-bonded carbons
G
G
C C
H
H
Cis-Isomer
(ii) Substituent G is on same side on the
double-bonded carbons

38
Geometrical isomers cont.
• They have different chemical and physical
properties.
• Each isomer can be converted to another
when enough energy is supplied, e.g. by
absorption of UV radiation or being heated at
around 300oC.
• The conversion occurs because the π bond
breaks when energy is absorbed, and the two
halves of the molecule can then rotate with
respect to each other before the π bond forms
again.

39
Geometrical isomers cont.
How to designate Trans or Cis

• When there is the same constituent attached to


the double bonded carbons, it is quite
straightforward to designate Trans or Cis.
• However, if there are more than one different
groups or atoms present, the situation becomes a
bit more complicated for assigning cis and trans
H Cl
Cl Cl H
F
C C C C C C
Cl H
Br Br Cl
I

Alkenes with different constituents on the double-


bonded carbons
40
Geometrical isomers cont.
oTo simplify this situation, the E/Z system is
used for naming geometrical isomers.
• Z stands for German zusammen, which means the same side
and
• E stands for German entgegen, meaning on the opposite side
oIn the E and Z system, the following rules
or steps are followed.
 On each C atom of the double bond, the priority of the atoms
bonded is assigned.

41
Geometrical isomers cont.
• The priority should be on the same basis as the
(R)/(S) system (i.e. on the basis of atomic
number).
 If the two higher priority groups of the two C
atoms are on the same side of the double bond, it
is called the (Z)-isomer.
 If the two higher priority groups of the two C
atoms are on opposite sides of the double bond, it
is called the (E)-isomer.

42
II. Optical isomers -
enantiomers
• Optical isomerism is a property exhibited by any
compound which have the same structure but differ in their
configuration due to molecular asymmetry (whose mirror
images are non-superimposable) rotate plane polarized
light.
• Racimic Enantiomers:
• The Greek word enantio means ‘opposite’.
• A chiral molecule and its mirror image are called enantiomers or
an enantiomeric pair, they rotate in equal amount in opposite
direction.
• Diastereoisomer: rotate in different amount
• Meso type optically active but doesn’t rotate at all.

43
Optical isomers cont.
• Are non-superimposable mirror image isomers can rotate the plane of
polarization of plane-polarized light.

W W CH3 CH3

X X H H
Z Z C2H5 C2H5
Y Y OH HO

Mirror image Mirror image


Enantiomers, Not (-)-2-Butanol (+)-2-Butanol
superimposable
The arrangement Enantiomers of 2-butanol
of W, X, Y and Z is
configuration

Enantiomers and configuration 44


Cont…

A B (i) B (ii)
plane-polarized light-
A : Before passing through a solution of an enantiomer,
B : After passing through a solution of an enantiomer
I. Clock-wise (right) rotation or Dextrorotatory (D) (+)
II. Anti-clock-wise (left) rotation or Levorotatory (L) (−) 45
Cont…
POLARIMETER; used to analyse the effect optical isomers
have on plane polarised light:

A B

C D
E
F

A Light source produces light vibrating in all directions


B Polarising filter only allows through light vibrating in one
direction
C Plane polarised light passes through sample
D If substance is optically active it rotates the plane polarised light
E Analysing filter is turned so that light reaches a maximum
F Direction of rotation is measured coming towards the observer

46
47
Optical isomers cont.
 Asymmetric compounds rotate plane
polarized light
 Magnitude of rotation depends upon:
1. The nature of the compound
2. The length of the tube usually expressed
in decimeters (dm)
3. The wavelength of the light source
employed; /λ/
4. Temperature of sample /T°/
5. Concentration of analyte
6. Concentration of solvent

48
Optical isomers cont.
The racemic mixture (racemates):
• A pair of enantiomers, each rotates the
plane-polarized light by the same amount,
but in the opposite direction.
• 50:50 mixtures of enantiomers are
called a racemic mixture.
• Racemic mixtures are optically ‘inactive’
(i.e. they cancel each other)
• The prefix () is used to specify the
racemic nature of such sample

49
Cont…Significance of + vs -

(-) (+
)

50
Cont…

Thalidomide

• The “Wonder Drug” Gone


Wrong

• 10,000-12,000 thalidomide
babies

• 46 affected countries

51
Cont...

52
Thalidomide Rises from the
ashes!
• Currently used for
• Cancer treatment

• Anti-inflammatory

• Treatment for leprosy

• HIV patients

ENL (Erythema Nodosum Laprosum)

53
Optical isomers cont.
Resolution
• A process where in enantiomers are
separated is called a Resolution.
• Convert the pair of enantiomers into a pair
of diastereomers
• Can be made by
• Chiral derivatising agents- acids, salts
• Chromatography- HPLC, GC, CC
• NMR spectroscopy: chiral shift reagents
• Enzymatic resolution

54
Representation of Molecules in
Three Dimension
• 1) Flying-wedge or Wedge-dash Projection: is the
most widely used three dimensional representation of
a molecule on a two dimensional surface (paper). This
kind of representation is usually done for molecule
containing chiral center.
• In this type of representation three types of lines are used.
• A bold wedge or thick line - it represents bond projection towards
the observer or above the plane of paper.
• A continuous line or ordinary line - it represents bond in the
plane of paper.
• A dashed wedge or broken line - it represents bond projection
away from theobserver or below the plane of paper. Example:- CH4

55
Cont…
2) Fischer Projections
• A 2D representation of chiral
molecules
• Vertical lines
• Represent bonds projecting behind
the plane of the paper
• Horizontal lines
• Represent bonds projecting out of
the plane of the paper
CHO CHO
CHO
H OH H OH
H C
CH2OH CH2OH
HO CH2OH

R-(+)- Glyceraldehyde

CHO CHO
CHO
HO H HO H
HO C
CH2OH CH2OH CH2OH
H

S-(+)- Glyceraldehyde
56
Cont...
3) D and L system
Emil Fischer used glyceraldehyde
as a standard for the D and L
H O
system of designating

configuration. H OH

• Glyceraldehyde
CH2OH
 Is an optically active molecule.
Glyceraldehyde
 can exist as enantiomers, i.e. (+)
and (-) forms, but the sign does
not describe the exact
configuration
57
cont...
• He arbitrarily took the (+) - glyceraldehyde enantiomer and assigned this as
D-glyceraldehyde
• The other enantiomer is the (-)-glyceraldehyde and this was assigned as L-
glyceraldehyde

H O
H O

 
H OH HO H

CH2OH CH2OH

(+)-D-Glyceraldehyde (-)-L-Glyceraldehyde

58
cont...
• It can easily be identified that the only difference in the
structures of D and L-glyceraldehyde is the orientation of
the hydroxyl group at the chiral centre.
• D-glyceraldehyde  –OH on the chiral C is on the
right
• L-glyceraldehyde  –OH on the chiral C is on the
left.
• One must remember that there is no correlation between
• D and L configurations, and
• (+) and (-) rotations.

59
Cont...
This D and L system is
• Common in biology/biochemistry,
especially with sugars and amino acids
(with amino acids, the –NH2 configuration is
compared with the –OH of glyceraldehyde)
• Particularly used to designate various
carbohydrate or sugar molecules, e.g. D-
glucose, L-rhamnose and L-alanine.
• The most generally useful, yet
suggested, way of specifying configuration
is the use of the prefixes R and S notation.

60
Cont...
4) (R) and (S) system (Cahn–Ingold–
Prelog system)
• A system of nomenclature that can describe
the configuration of enantiomers more
precisely/ absolute configurations of chiral
compounds.
• R and S came from the Latin words rectus
and sinister, meaning right and left,
respectively.
• The following rules or steps are applied for
designating any enantiomer as R or S.

61
Cont...
1. Arrange the ligands associated with an
element of chirality into order of priority.
• Priority Rules
• Higher atomic number is given higher
priority.
• Higher atomic mass is given higher priority
(for isotopes).
• When the proximate atoms of two or more of
the ligands are the same, the atomic number
of the next atom determines the priority; i.e.
• Proximal groups take priority over distal
groups
62
Cont...
• Double and triple bonds are counted as if they were split into two or
three single bonds, respectively

C O
As if it
C O
were O C

N C

C N
As if it
C N were N C

Examples of groups containing double or triple


bonds (π bonds) and their interpretation
63
Cont...
2. View the molecule with the lowest priority
group pointing away from the viewer.

3. Count the remaining ligands in order of


decreasing priority.

• If the path traced is clockwise, R absolute


configuration is assigned

• If the path traced is counterclockwise, S


absolute configuration is assigned.
64
1. Each of the four groups attached to the chiral
carbon is given order of priority
3
CH3

1 Priority determination in 2-
HO H 4
hexanol
2 CH2CH2CH3

2. View the molecule with the lowest priority


group pointing away from the viewer.
3 3
CH3 CH3

1
 Rotate 4 H
HO H 4 d to 1 Viewer
OH
2 CH2CH2CH3
2CH2CH2CH3

The least priority H atom (4) is away from the viewer


65
3. Count the remaining ligands in order of decreasing priority.
• An arrow from group 1→ 2 → 3 is to be drawn.
• If the path traced is clockwise, R absolute configuration is
assigned.
• If the path traced is counterclockwise, S absolute
configuration is assigned.

3
CH3

4 H
1 Viewer
OH

2CH2CH2CH3

(R)-2-Hexanol Priority order


1 to 4 is in clock-wise direction

lustrative steps to assign R and S taking 2-hexanol as an example


66
SAWHORSE FORMULA
• Indicates the arrangement of all the atoms or
groups on two adjacent carbon atoms. The
bonds between the two carbon atoms are drawn
diagonally and of relatively greater length for
the sake of clarity. The lower left hand carbon is
taken as the front carbon or towards the
observer and the upper right hand carbon as the
back carbon or away from the observer. e.g.
ethane

67
NEWMAN PROJECTION

• Newman devised a very simple method of projecting three


dimensional formulas on
two dimensional paper which are known as Newman
projection.
• In these formulae the molecule is viewed from the front or
along the axis of a carbon-carbon
bond.
• The carbon nearer to the eye is represented by a point and
the carbon atom towards the rear
by circle.
• The three atoms or groups on the carbon atoms are shown
as being bonded to dot or circle by
an angle of 1200 to each other.
• In Newman formula all parallel bonds are eclipsed or all anti
parallel or opposite bonds are
staggered.

68
CH3CH2CH2CH3

• Eclipsed means that identical groups are


all directly in line with one another,
Gauche means that identical groups are
60 degree from one another and anti
means that identical groups are 180
degree from one another.

69
Chair and boat
cyclohexane ring
contain molecules

70
How many stereogenic centers does each
molecule have?
Br

A)

Br

B)

CO2H O

H
B) N OH
H2N N
H

O O
SH
71
Which group in each pair has the highest priority?

A) -CH3 or -CH2CH3

B) -I or -Br

C) -CH3Br or -CH2CH2Br

Rank in order of decreasing priority:

A) -COOH -H -NH2 -OH

C CH H
B) C CH2 CH3
H

72
Label each compound as R or S.
Cl
A)
H
H3C Br

CH2Br

B)
ClH2C
OH
H3C

73
Enantiomers, Diastereomers
and Meso Cpds
Enantiomers
• Enantiomers are mirror image isomers
• Have the same connectivity and opposite
designations (eg, the enantiomer of (2R,3R-
Tartaric acid is (2S,3S)- tartaric acid) at
respective chiral centers
• Have identical physico-chemical properties
• Illustrative example, 2,-Bromo,3- chloro
butane
• There are two chiral carbons
• The chiral centers are at C-2 and C-3.
• The maximum number of possible isomers will be 2n = 22 = 4.

74
Cont…
CH3
CH3
S Enantiomers R
H Br
Br H

Cl H
S H Cl R
CH3
CH3

(2S,3S) 2-bromo-3-chlorobutane (2R,3R) 2-bromo-3-chlorobutane

CH3 CH3
R
Br H H Br S

Cl H S H Cl R
Enantiomers
CH3 CH3

(2R,3S) 2-bromo-3-chlorobutane (2S,3R) 2-bromo-3-chlorobutane


75
Enantiomers, Diastereomers and
Meso Cpds..
Diastereomers
• They are not mirror images to each other
• Require the presence of two or more chiral centers.
• They have the same connectivity but share the
same configuration at least at one point but
not all chiral centers. (eg, the diastereomer of
(2R,3R-Tartaric acid is (2R,3S)- tartaric acid)
• Have different physical and chemical properties.
• Different mp, bp, solubility, densities, refractive indexes and
so on
• Differ in specific rotation
• May have the same or opposite signs of rotation, or Some may be
inactive

Illustrative example, 2,-Bromo,3- chloro butane

76
Cont…
CH3 CH3
S R
H Br Br H
Diastereomers
Cl H S H Cl R

CH3 CH3

(2S,3S) 2-bromo-3-chlorobutane (2R,3R) 2-bromo-3-chlorobutane

CH3 CH3
R
Br H H Br S
Diastereomers

Cl H S H Cl R

CH3 CH3

(2R,3S) 2-bromo-3-chlorobutane (2S,3R) 2-bromo-3-chlorobutane


77
Enantiomers, Diastereomers and
Meso Cpds..
oMeso compounds
• A meso compound is one whose molecules are superimposable
with their mirror image
• A meso compound is optically inactive because the chiral centers
of the molecule rotates in the same amount but in opposite
direction this nullifies the reading. Net specific rotation is zero
• Has a plane of symmetry this make them achiral compound but
has more than one chiral centers (atoms). CH3

• Has at least two chiral carbons


Cl H

Cl H

Mes
CH3
o
78
Can be superimposed by 180 rotation.
o
Diastereomers and Meso compounds
cont.
All meso compounds can be considered
diastereomers, not all diastereomers are meso
compounds

In tartaric acid


• There are two chiral carbons
• Four isomeric forms are theoretically expected (2 n = 22 = 4).
• However, because one half of the tartaric acid molecule is a
mirror image of the other half, we get a meso structure.
• This means this compound and its mirror image are
superimposable, i.e. they are the same compound.
• Thus, instead of four, we obtain only three stereo isomers for
tartaric acid
79
Enantiomers, Diastereomers and Meso Cpds..

80
Enantiomers, Diastereomers and
Meso Cpds..

81
Which of the following are meso compounds?

A) D) O

B) E)

Cl
C)

OH

82
Label the stereogenic centers and draw all
stereoisomers.
A)
CH3CH2CH(Cl)CH(OH)CH2CH3

83
Answer

A)
CH3CH2CH(Cl)CH(OH)CH2CH3

H3CH2C CH2CH3 H3CH2C CH2CH3

H H H H
OH HO Cl
Cl

H3CH2C CH2CH3
H3CH2C CH2CH3
H OH
H HO H
Cl
H Cl

84
Brainstorming
• What is the need to study stereoisomerism in
Pharmacy?

85
Significance of R vs S

86
87
88
What is the need to study stereoisomerism in Pharmacy?

• Pharmacy is a discipline that deals with various aspects of drugs.

• All drugs are chemical entities, and great majorities (30-50 %) of


them

• contain stereo centers, show stereoisomerism


and exist as enantiomers

89
Significance of …cont.
• Currently there is a rapid increase of the sales
of chiral drugs in drug markets

• It is therefore important to understand


• How drug chirality affects its interaction with drug targets

• One enantiomeric form of a drug may be active, and the other may
be inactive, less active or even toxic.
• Proper nomenclature in describing the drugs themselves

90
Significance of …cont.
• Most often only one form
shows correct physiological
and pharmacological action.
• For example,
• Only one enantiomer of morphine is
active as an analgesic

• Naturally occurring levo-


morphine produces
potent analgesic
• Only one enantiomer of glucose, D-
glucose is metabolized in our body to
give energy
• Only one enantiomeric form of
adrenaline is a neurotransmitter.

91
Significance of …cont.
• Most of the molecules that make up living organisms
are chiral, i.e. show stereoisomerism.
• For example, all but one of the 20 essential amino
acids are chiral.
• Thus, it is important to understand stereochemistry for
a better understanding of drug molecules, their action
and toxicity.

92
Significance of …cont.
• Two enantiomers of limonene produce two distinct
flavours:
• (-)-limonene is responsible for the flavour of lemons
and
• (+)-limonene for orange.

H
H  

(+)-Limonene (in orange)


(-)-Limonene (in lemon)
93
Summary

• Chiral molecule - has the property of


handedness
• Not superposable on its mirror image
• Can exist as a pair of enantiomers
• Achiral molecule superposable on its
mirror image
• Many drugs contain chiral molecules

94
Cont…

• About more than half of the drugs


currently in use are chiral compounds and
near 90% of the last ones are marketed
as racemates.
• Therefore, it is important to promote the chiral
separation and analysis of racemic drugs in
pharmaceutical industry as well as in clinic.
95
THANK YOU
ALL !!

ANY QUESITIONS

96

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