Isom ers

Isomers: different compounds with the

same molecular formula
Constitutional isomers: isomers with a
different connectivity
Stereoisomers: isomers with the same
molecular formula, the same connectivity
but a different orientation of their atoms in
space that cannot be interconverted by
rotation about a single bond

1
Iso me ri sm → Constit uti ona l
Iso me rs a nd S te reoi so me rs
Ster eois omer s are is omer s wi th th e same
mo le cul ar formu la an d same co nnect iv it y
of at oms bu t di ffer en t ar ran ge men t of
at oms in spa ce

2
 St ereoc hem is try
is the chemistry of molecules in three dimension

3
 Handed nes s
Stereochemistry of organic molecules can be
understood, if we understand the meaning of
handedness
the fundamental reason for this is that our
hands are not identical, rather they are mirror
images

4
 Ch ira lity

The mirror image Objects which are chiral have a

of a chiral object is sense of “handedness” and
different and will not exist in two forms.
superimpose on the
original object.
5
The reason for Handedness→ chirality
• Although everything has a mirror image, mirror images
may or may not be superimposable.
• Some molecules are like hands. Left and right hands are
mirror images, but they are not identical, or
superimposable → chiral (property of handedness)

6
Mirr or I ma ge

7
Chiralit y a nd Non chir alit y
Mirror image: the reflection of an object in a
mirror
Objects that are not superposable on their mirror
images are said to be chiral, that is, they show
handedness
Objects that are superposable on their mirror
images are said to be achiral, that is, they do not
show handedness. An achiral object has at least
one element of symmetry

8
 Achiral Molecules
• Do these molecules contain a Plane of Symmetry (Mirror Plane)?

9
 Chiral Molecules
• The molecule labeled A and its mirror image labeled B
are not superimposable. No matter how you rotate A and
B, all the atoms never align. Thus, CHBrClF is a chiral
molecule, and A and B are different compounds.
• A and B are stereoisomers—specifically, they are
enantiomers.
• A carbon atom with four different groups is a tetrahedral
stereogenic center.

10
 Chiral vs. Achiral
• With one stereogenic center, a molecule
will always be chiral.

• With two or more stereogenic centers, a

molecule may or may not be chiral, e.g.
Meso compound (contains a plane of
symmetry or a mirror plane)

11
 Chiral vs . Ach ira l
Chiral: from the Greek, cheir, hand
an object that is not superposable on its mirror
image
Achiral: an object that lacks chirality; one that
lacks handedness
an achiral object has at least one element of
symmetry
plane of symmetry: an imaginary plane passing
through an object dividing it so that one half is
the mirror image of the other half
center of symmetry: a point so situated that
identical components are located on opposite
sides and equidistant from that point along the
axis passing through it

12
 Ele ments of Sy mme try
Symmetry in objects

13
Plane of Symmetry or Mirror plane

14
TWO VIEWS OF THE PLANE OF SYMMETRY

plane of
symmetry

F F

Cl Cl
Br Cl
Br
Cl
F side edge
Cl
Br view view
 Pla ne of Sy mm et ry

Symmetry plane No symmetry plane

COOH CH3
H C H H C OH
COOH COOH

achiral chiral

16
Eleme nts o f Sy mmetry

Center of symmetry: a point so situated

that identical components of the object are
located equidistant on opposite sides and
equidistant from the point along any axis
passing through the point

Br H

Cl
Cl

H Br center of  
symmetry
17
 Ch ira l Cen ter
The mo st comm on ( but n ot the only)
ca use of chi ra li ty i n orga ni c mol ecules
is a tetr ah edra l atom , mo st comm on ly
ca rb on, bond ed to f our di ff erent
groups

A ca rbon wi th four di ff erent group s

bonded to it is cal led a chira l center
al l ch ira l cen ter s ar e st ere ocen ter s, bu t
no t all st er eocen ter s ar e chi ral cen ter s.

18
STEREOGENIC CARBON ATOMS
 Stere og en ic Carb on
At oms

Cl Thi s is on e ty pe of ….
stereocenter
…. others are possible

H F
Br
A stereogenic carbon is tetrahedral and
has four different groups attached.
20
 Stereogenic Centers
• To locate a stereogenic center, examine the four groups
—not the four atoms—bonded to each tetrahedral
carbon atom in a molecule.
• Omit from consideration all C atoms that cannot be
tetrahedral stereogenic centers. These include
• Methylene and methyl units, i. e. CH2 and CH3 groups
respectively.
• Any sp or sp2 hybridized Carbons, e.g. triple bonds,
and double bonds in alkenes (C=C) and carbonyls
(C=O).

21
Enantiomers

22
 Enantiomers

One of a pair of molecular species that

are mirror images of each other and
not superposable.

They are mirror-image stereoisomers.

23
 Drawing Enantiomers
• To draw both enantiomers of a chiral compound such as
2-butanol, use the typical convention for depicting a
tetrahedron: place two bonds in the plane, one in front of
the plane on a wedge, and one behind the plane on a
dash. Then, to form the first enantiomer, arbitrarily place
the four groups—H, OH, CH3 and CH2CH3—on any bond
to the stereogenic center. Then draw the mirror image.

24
Pairs of Enantiomers

25
 Enantiomer s

Cl Cl rotate

H F F
Br Br H

this molecule
is chiral
Cl
note that the fluorine
and bromine have been
interchanged in the

H Br enantiomer

F 26
 Enantiomer s

HO O O OH
Lactic acid C C

C C
HO H H OH
CH3 H3 C

27
 Enantiom ers
3-Chlorocyclohexene
Cl Cl

28
 Enantiom ers
OH
CH3 CHCH2 OH
1,2-propanediol
OH OH

H3 C C CH2 OH HOH2 C C CH3

H H

29
 Enantiom ers
A nitrogen chiral center

+ +
N N
H3 C CH2 CH3 CH3 CH2 CH3
A pair of enantiomers

30
 Enanti ome rs
&
Diaste reomers
31
 En antiomers &
Dia stereois om er
Enantiomers: opposite configurations at
all stereogenic centers.
Diastereomers: Stereoisomers that are
not mirror images of each other.
Different configuration at some
locations.

32
 Two Stereocenters
Cl Br Br Cl
d
H3C CH3 H3C CH3 i
a
H H H H s
t
entaiomers e
r
Cl Br Br Cl o
m
e
r
H3C H H CH3 s

H CH3 H3C H

entaiomers
33
 En antiomers &
Dia ster eome rs
For a molecule with 1 stereocenter, 2
stereoisomers are possible
For a molecule with 2 stereocenters, a
maximum of 4 stereoisomers are possible
For a molecule with n stereocenters, a
maximum of 2n stereoisomers are possible
2n-1 pairs of enantiomers

34
 Dia ster eome rs
2,3,4-Trihydroxybutanal
two chiral centers
22 = 4 stereoisomers exist; two pairs of
enantiomers
CHO CHO CHO CHO
H C OH HO C H H C OH HO C H

H C OH HO C H HO C H H C OH

CH2 OH CH2 OH CH2 OH CH2 OH

A pair of enantiomers A pair of enantiomers
(Erythreose) (Threose)

Diastereomers:
stereoisomers that are not mirror images
refers to the relationship among two or more
objects 35
 Dia stereome rs
2,3-Dihydroxybutanedioic acid (tartaric acid)
two chiral centers; 2n = 4, but only three
stereoisomers exist

COOH COOH COOH COOH

H C OH HO C H H C OH HO C H

H C OH HO C H HO C H H C OH

COOH COOH COOH COOH

A meso compound A pair of enantiomers
(plane of symmetry)
Meso compound: an achiral compound
possessing two or more chiral centers that
also has chiral isomers
36
Enantiom ers & D ia stereom ers
2-Methylcyclopentanol

CH3 OH HO H3 C

H H H H
cis­2­Methylcyclopentanol
  (a pair of enantiomers) diastereomers

CH3 H H H3 C

H OH HO H
trans­2­Methylcyclopentanol
    (a pair of enantiomers)

37
 Dia stereome rs
1,2-Cyclopentanediol

OH HO OH HO

H H H H
cis-
1,2-Cyclopentanediol
(a meso compound)
diastereomers

OH H H HO

H HO OH H
trans-
1,2-Cyclopentanediol
(a pair of enantiomers)

38
 Dia ster eome rs
cis-3-Methylcyclohexanol

H3 C OH HO CH3

39
 Dia ster eome rs
trans-3-Methylcyclohexanol

H3 C CH3

OH HO

40
 Mes o comp ou nds

Meso compounds are achiral by virtue of a

symmetry plane, but contain a stereogenic
center.

plane of symmmetry mirror

Cl Cl Cl Cl

H3C CH3 H3C CH3

H H H H

41
 Mes o comp ou nds
Meso compound: achiral despite the
presence of stereogenic centers
Not optically active
Superposable on its mirror image
Has a plane of symmetry

42
The Three Stereoisomers of
2,3-dibromobutane

• Because one stereoisomer of 2,3-dibromobutane is

superimposable on its mirror image, there are only three
stereoisomers, not four.
43
 NUMBER OF
STEREOISOMERS POSSIBLE
 How Many Stereoisomers
Are Possible?

maximum number of stereoisomers

sometimes fewer = 2 n
,
than this number
will exist

where n = number of stereocenters

(sterogenic carbons)
 CH2OH OH RR
RS
CH3 *
C CH2 CH CH CH3 SR
* SS
CH3 CH3
22 = 4 stereoisomers
CH3
RRR RSS
* RRS SRS
RSR SSR
*
* OH SRR SSS

CH3 CH
CH3 23 = 8 stereoisomers
 CONFIGURATION

ABSOLUTE CONFIGURATION ( R / S )
 CONFIGURATION

The three dimensional arrangement of the

groups attached to an atom

Stereoisomers differ in the configuration at one or

more of their atoms.
 CONFIGURATION
→ R,S convention

1 2 counter
clockwise 2 1
clockwise
C C
4 4
3 3
view with
substituent
of lowest
priority in
back
R (rectus) S (sinister)
 Rules for Labeling Stereogenic Centers with R or S

• Since enantiomers are two different compounds, they

need to be distinguished by name. This is done by
adding the prefix R or S to the IUPAC name of the
enantiomer.
• Naming enantiomers with the prefixes R or S is called
the Cahn-Ingold-Prelog system.
• To designate enantiomers as R or S, priorities must be
assigned to each group bonded to the stereogenic
center, in order of decreasing atomic number. The atom
of highest atomic number gets the highest priority (1).

50
Priority Rules for Naming Enantiomers (R or S)

• If two atoms on a stereogenic center are the same,

assign priority based on the atomic number of the atoms
bonded to these atoms. One atom of higher priority
determines the higher priority.

51
Priority of Isotopes on a Stereogenic Center
• If two isotopes are bonded to the stereogenic center,
assign priorities in order of decreasing mass number.
Thus, in comparing the three isotopes of hydrogen, the
order of priorities is:

52
Priority Rules for Multiple Bonds in (R or S) Labeling
• To assign a priority to an atom that is part of a multiple bond,
treat a multiply bonded atom as an equivalent number of
singly bonded atoms. For example, the C of a C=O is
considered to be bonded to two O atoms.

• Other common multiple bonds are drawn below:

53
Examples Assigning Priorities

54
Ca hn-Ingold -P relog S ys tem f or
Na min g E nantiome rs R or S

55
R or S Enantiomers

56
Positioning the Molecule for R/S Assignment

57
R-enantiomer (Clockwise Rotation)
S-enantiomer (Counterclockwise Rotation)

58
Manipulation of Chiral Molecules

59
The molecule is rotated to put the lowest
priority group back
If the groups descend in priority (a,b then c) in
clockwise direction the enantiomer is R
If the groups descend in priority in
counterclockwise direction the enantiomer is S

60
 R,S Con ven tion
Priority rules (Cahn, Ingold, Prelog)
Each atom bonded to the stereocenter is
assigned a priority, based on atomic
number. The higher the atomic number,
the higher the priority
1 6 7 8 16 17 35 53
H CH 3 NH 2 OH SH Cl Br I

Increasing Priority

61
 R,S Con ven tion
If priority cannot be assigned on the basis
of the atoms bonded to the stereocenter,
look to the next set of atoms. Priority is
assigned at the first point of difference.

1 6 7 8
CH 2 H CH 2 CH 3 CH 2 NH 2 CH 2 OH

Increasing Priority

62
 R,S Con ven tion
Atoms participating in a double or triple
bond are considered to be bonded to an
equivalent number of similar atoms by
single bonds
C C
is treated as
-CH=CH2 -CH-CH2

O O C
is treated as
-CH C O
H
C C
is treated as
C CH C C H
C C

63
 Priorit ie s
-OH H
HO COOH
-COOH C
-CH3 CH3

-H (R)-(-)-lactic acid

H
HOOC OH
C
CH3

(S)-(+)-lactic acid 64
Bromochlorofluoroiodomethane
1 1
I I
4 4
F C C
2 F
Cl Br Br Cl
3 3
2

R S
Enantiomers 65
R and S Assignments in Compounds
with Two or More Stereogenic Centers.
• When a compound has more than one stereogenic
center, the R and S configuration must be assigned to
each of them.

One stereoisomer of 2,3-dibromopentane

The complete name is (2S,3R)-2,3-dibromopentane

66
St ereois om eris m of Cyc li c
Compo un ds
1,4-dimethylcyclohexane
Neither the cis not trans isomers is optically active
Each has a plane of symmetry

67
1,3-dimethylcyclohexane
The trans and cis compounds each have two
stereogenic centers
The cis compound has a plane of symmetry
and is meso
The trans compound exists as a pair of
enantiomers

68
Prop ert ies of St ereois om ers

69
Prop ert ies of Stere oiso mers
Enantiomers have identical physical and
chemical properties in achiral
environments
Diastereomers are different compounds
and have different physical and
chemical properties
meso tartaric acid, for example, has
different physical and chemical properties
from its enantiomers (see Table 3.1)

70
 Pla ne-P olarized L ig ht

Ordinary light: light vibrating in all

planes perpendicular to its direction of
propagation
Plane-polarized light: light vibrating only
in parallel planes
Optically active: refers to a compound
that rotates the plane of plane-polarized
light

71
Pla ne-P olarized L ig ht
plane-polarized light is the vector sum of
left and right circularly polarized light
circularly polarized light reacts one way
with an R chiral center, and the opposite
way with its enantiomer
the result of interaction of plane-polarized
light with a chiral compound is rotation of
the plane of polarization

72
 Pla ne-P olarized L ig ht

Polarimeter: a device for measuring the

extent of rotation of plane-polarized
light

73
 Optica l Act iv it y
ob serv ed rotation : th e num ber of deg re es , α,
th rou gh which a comp ou nd rotate s th e plan e of
pol ariz ed li ght
dex tro rota tor y (+) : refers to a comp ou nd that
rotates the pl ane of polari zed li ght to the ri gh t
levorotatory (-): re fers to a comp ou nd that rota tes
of the pl ane of polari zed li ght to the lef t
specif ic rotati on: ob serv ed rotation when a pure
samp le is pl ac ed in a tu be 1.0 dm in l eng th and
con ce ntration in g/mL ( den sity); for a sol uti on,
con ce ntration is ex pres sed in g/ 100 mL
COOH COOH
C H H C
H3 C OH CH3
HO
(S)­(+)­Lactic acid (R)­(­)­Lactatic acid
21 21
[α]D = +2.6° [α]D = ­2.6°

74
 Opti cal Purit y
Optical purity: a way of describing the
composition of a mixture of enantiomers

[α ]sam ple
Percent optical purity = x 100
[α ]pure enantio mer
Enantiomeric excess: the difference between
the percentage of two enantiomers in a
mixture
[R] ­ [S]
Enantiomeric excess (ee) = x 100 = %R ­ %S
[R] + [S]

optical purity is numerically equal to enantiomeric

excess, but is experimentally determined

75
 Res olu ti on

Racemic mixture: an equimolar mixture

of two enantiomers
because a racemic mixture contains equal
numbers of dextrorotatory and levorotatory
molecules, its specific rotation is zero
Resolution: the separation of a racemic
mixture into its enantiomers

76
 Racemates
• An equal amount of two enantiomers is called a
racemate or a racemic mixture. A racemic mixture is
optically inactive. Because two enantiomers rotate
plane-polarized light to an equal extent but in opposite
directions, the rotations cancel, and no rotation is
observed.

77
 Specific Rotation
• Specific rotation is a standardized physical constant for
the amount that a chiral compound rotates plane-
polarized light. Specific rotation is denoted by the
symbol [α] and defined using a specific sample tube
length (l, in dm), concentration (c in g/mL), temperature
(25 0C) and wavelength (589 nm).

78
Dis cov er y o f E nantiome rs

“There is no doubt
that in dextro - +
COO Na
tartaric acid there
exists an H C OH
assymetric
arrangement HO C H
having a
nonsuperimposible - +
COO Na
image.”

79
 OH OH meso
HOOC COOH
H
Tartaric Acid
H

OH OH OH OH
HOOC H H COOH
H COOH HOOC H

(+)-tartaric acid (-)-tartaric acid

enantiomers

OH OH meso ALSO FOUND

(as a minor component)
HOOC COOH
H H [α ]D = 0
more about this
meso -tartaric acid compound later
OH OH OH OH 80
 Diastereoisomer
Stereoisomers
that are not
mirror images of H
COOH
NH 2
COOH
H2N C H
each other. C
Different C C
H OH H OH
configuration at CH 3 CH3
some locations.

81
 Diastereomers
Threonine: 2 pairs of H
COOH
NH2 COOH
H 2N H
enantiomers C C
C C
H OH HO H
CH3 H3C
2R,3R 2S,3S 2R,3S & 2S,3R 2R, 3R 2S, 3S
2S,3S 2R,3R 2R,3S & 2S,3R COOH COOH
2R,3S 2S,3R 2R,3R & 2S,3S H C NH2 H 2N C H
2S,3R 2R,3S 2R,3R & 2S,3S C C
HO H H OH
H3C CH3

2R, 3S 2S, 3R

82
Enantiomers & Diastereomers
For tartaric acid, the three possible
stereoisomers are one meso compound
and a pair of enantiomers.

Meso compound: an achiral compound

possessing two or more stereocenters.

83
 Symmetry Plane
2R, 3S and 2S, 3R COOH COOH
HO H
are identical H C OH C
C C
Molecule has a plane HO H H OH
COOH COOH
of symmetry 2R, 3R 2S, 3S
perpendicular to C-C COOH COOH
and is therefore H C OH HO
C
H

achira C C
H OH HO H
COOH COOH

2R, 3S 2S, 3R

84
 Symmetry Plane
2R, 3S and 2S, 3R COOH COOH
H
are identical H C OH HO
C
Molecule has a plane HO
C
H H
C
OH
of symmetry COOH COOH
perpendicular to C-C 2R, 3R 2S, 3S

and is therefore COOH

Mirror
COOH
HO H
achira H C OH
Cimage is
One meso H
C
OH HO
Cidentical
H
compound and a COOH COOH

pair of enantiomers 2R, 3S 2S, 3R

85
 CH3CHCHCH3
Cl Br
2-Bromo-3-chlorobutane
mirror
Cl Br Br Cl
S R S R
CH3 CH3 CH3 CH3
H H H H
enantiomers 1
diastereomers
Cl Br Br Cl
S S R R
CH3 H H CH3
H CH3 CH3 H
enantiomers 2

86
 CH3CHCHCH3
Cl Cl
2,3-Dichlorobutane
Cl Cl Cl Cl
S R mirror image
CH3 CH3 CH3 is identical CH3
H H H H
meso
diastereomers
Cl Cl Cl Cl
S S R R
CH3 H H CH3
H CH3 CH3 H
enantiomers

87
 Tartaric Acid
(-) - tartaric acid (+) - tartaric acid
[α ]D = -12.0o [α ]D = +12.0o
mp 168 - 170o mp 168 - 170o
solubility of 1 g solubility of 1 g
0.75 mL H2O 0.75 mL H2O
1.7 mL methanol 1.7 mL methanol
250 mL ether 250 mL ether
insoluble CHCl3 insoluble CHCl3
d = 1.758 g/mL d = 1.758 g/mL

meso - tartaric acid

[α ]D = 0o solubility of 1 g
mp 140o 0.94 mL
H 2O 88
Fische r Pr ojectio ns

89
 CH3

H OH

Fis ch er Pr oject ion s CH2 CH3

Fischer projection: a two-dimensional

representation showing the
configuration of a stereocenter
horizontal lines represent bonds projecting
forward
vertical lines represent bonds projecting to
the rear
the only atom in the plane of the paper is
the stereocenter

90
 Fis ch er Pr oject ion s

COOH COOH
C H OH
H
OH CH3 CH3
How?
(R)-lactic acid
91
 Fisc her Pro ject ion s

COOH COOH

H C H OH
OH CH3 CH3

92
 Fis ch er Pr oject ion s

COOH COOH
H OH H OH
CH3 CH3
93
 Fis ch er Pr oject ion s

 Orient the stereocenter so that bonds

projecting away from you are vertical and
bonds projecting toward you are horizontal
 Flatten it to two dimensions
OH CH3 CH3
(1)
H C H C OH (2) H OH
CH3
CH3 CH2
CH2 CH3 CH2 CH3
(S)­2­Butanol       (S)­2­Butanol 
(3­D formula) (Fischer projection)
94
Assigning R,S Configuration
Lowest priority group goes to the top.
View rest of projection.
A curved arrow from highest to lowest
priority groups.
Clockwise - R (rectus)
Counterclockwise - S (sinister)

95
Assigning R,S Configuration
4

H
2
3 H 3C COOH
OH
1 s-lactic acid
96
 Rules of Motion
 Can rotate 180°, but not 90° because
90° disobeys the Fischer projection.
Same groups go in and out of plane

COOH COOH CH3

CH 3
H OH 180 HO H
=H OH HO H =
CH3 CH3 COOH COOH

97
 Rules of Motion
 Can rotate 180°, but not 90° because
90° disobeys the Fischer projection.
Different groups go in and out of plane
This generates an enantiomeric structure
COOH COOH H
H
H OH 90 H3C COOH
=H OH H3C COOH =
CH3 CH3 OH OH

(R)-lactic acid (S)-lactic acid

98
 Rules of Motion
 One group can be held steady and the
others rotated.

COOH COOH
H OH same as HO CH3
CH3 H

99
 Rules of Motion
To determine if two Fischer projections
represent the same enantiomer carry
out allowed motions.
H C 2H 5 OH
H 3C C 2H 5 HO H H CH3
OH CH3 C2H 5

A B C
100
 H C2H 5 OH
H 3C C2H 5 HO H H CH3
OH CH 3 C2H 5

Rules of Motion A B C

By performing two allowed movements

on B, we are able to generate
projection A. Therefore, they are
identical.
CH2CH 3 HO H
CH3 CH3CH2
HO H H CH2CH3 CH3 CH 2CH3
CH 3 CH 3 HO

B A

101
 H C2H 5 OH
H 3C C2H 5 HO H H CH3
OH CH 3 C2H 5

Rules of Motion A B C

Perform one of the two allowed motions

to place the group with lowest priority
at the top of the Fischer projection.

OH CH 2CH3 H
H CH 3 180 H OH CH 3
H 3C CH 2CH
90
CH 2CH3 OH OH

C not A
102
 Priorities
HOOC
NH2 CH3
H
H 2N H HOOC NH2
COOH CH3 CH3
CH3
H
H H HOOC
HOOC NH2 HOOC NH2
CH3 CH3 H 2N H
CH3
S - stereochemistry 103
 1-Bromo-2-chlorocyclohexane
Br Cl Cl Br cis

enantiomers
diastereomers

Br Br tran s

Cl Cl
enantiomers
104
 1-Bromo-2-chlorocyclopropane

Br R Cl Cl R Br
S S
cis

enantiomers
diastereomers
Br Br
R R S S
tra ns
Cl Cl

enantiomers
105
 1,2-Dibromocyclopropane
mirror image identical

Br Br Br Br
ci s

meso
diastereomers

Br Br
tra ns
Br Br

enantiomers 106
Biol ogi cal Signif ic ance of St ereois om ers

Structure causes Properties

Stereochemistry Biological effects

Example
•Pasteur’s plant mold metabolized (+)-tartaric acid but not (-)-tartaric acid

107
 Bio logi ca l Si gn ifi canc e of Stereois om ers
Th alido mi de
O
•Marketed in 50 countries 1956-1962
Sedative for “hysterical” pregnant women
N O
Antiemetic to combat morning sickness
N
•Caused thousands of birth defects
O O H

Teratogen: causes fetal

abnormalities One stereocenter

•Sold as racemic mixture: 1:1 mixture of enantiomers

R enantiomer = antiemetic (not teratogenic)
S enantiomer = teratogenic (not antiemetic)
•Single-enantiomer drug not useful: quickly racemizes in body

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 Biol ogi cal Si gn ific ance of
St ereois om ers
Another Biological Effect: Odor
O O
enantiomers

H H

(R)-(-)-carvone (S)-(+)-carvone
smells like spearmint smells like caraway

Mirror image molecules do not have “mirror image effects”

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 Biologi cal S igni fica nce of
Stereo isom ers
Of Han ds, Gl ov es, and B iol ogy
Why do stereoisomers have different biological properties?
•Many biological effects involve interaction with a cavity in enzyme or receptor
•Good fit to cavity (i.e., strong binding) triggers enzyme or receptor
R H

OH
•Enzymes and receptors are proteins; built from amino acids: H2N

O
•Most amino acids are chiral, so protein cavity is also chiral
•Metaphor: Stereoisomer = left hand or right hand
Protein hole = left glove or right glove
Left hand fits left glove but not right glove
Left hand triggers “left protein” but not “right protein”
•(R)-carvone triggers spearmint smell receptor but not caraway smell
receptor

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