Designating Handedness Using Fischer Formulas

Presentation by Nourelle M.
Calam
Designating
Handedness Using
Fischer Projection
Formulas
1
Presentation by Nourelle M. Calam
What are
Carrying the name of their original
Fischer creator, the German chemist Hermann
Emil Fischer, Fischer projection formula
Projection is a two-dimensional structural notation
for showing the spatial arrangement of
Formulas groups about chiral centers in molecules.
2
To create a visual representation of chiral
molecules that exist in nature as 3D objects, we
make use of the Fischer projection formula.
Fischer A Fischer projection or Fischer projection

Projection formula is a convention used to depict a
stereoformula in two dimension without
Formula: destroying the stereochemical information, i.e.,
what for? absolute configuration, at chiral centers.
Used to represent a 3D object using a 2D image.
3
In a Fischer projection formula, a chiral center is

represented as the intersection of vertical and
horizontal lines. The atom at the chiral center, is
Fischer no longer explicitly shown.
Projection
There's carbon
Formula here
4
Important notice:
Fischer The remaining discussions in this section
Projection involves drawing Fischer projection formulas to

denote molecular chirality for molecules.
Formula Specifically, all examples moving forwards will
be on monosaccharides.
5
Fischer Projection
Formulas for
Monosaccharides
6
How do we differentiate one from the
Monosaccharides other?
Recall that
monosaccharides are the
simplest types of
carbohydrates, and are
either polyhydroxy
aldehydes, or polyhydroxy
ketones.
7
Consider Glyceraldehyde
The simplest
monosaccharide that has a
chiral center is the 3-
carbon polyhydroxy
aldehyde Glyceraldehyde
(2,3-dihydroxypropanal)
8
9
By convention, in a Fischer
formula for a
monosaccharide, the
carbon chain is always
positioned vertically, with
the carbonyl group
(aldehyde or ketone) at or
near the top.
10
11
The intersection of the vertical and horizontal lines

indicate the presence of a chiral center.
12
*Attachments on the chiral center (also called the

stereocenter) can be interchanged, leaving you with two
isomers of this compound.
13
Let's have another

example
14
2,3,4-trihydroxybutanal
is
is a monosaccharide with 4
carbons and two chiral centers
15
is converting this to its Fischer formula equivalent,
where the two chiral centers indicate the
intersection of vertical and horizontal lines, we
would have 4 isomers of this compound
16
is
17
D and L, what do they

mean?
is
18
D and L, what do they mean?

is
The D, L system is used to designate the
handedness of molecules. Remember, molecules
which posses the property of handedness exist in
nature as having two forms, a left-handed form,
and a right-handed form.
19
How do the D,L system help us

identify which is which?
is
here's how
20
The D,L system

is
To designate the handedness of a

monosaccharide with one or more than chiral
center, we follow these steps:
21
Start
counting
here!
The D,L system

is 1. The carbon chain is numbered
starting at the carbonyl group
end of the molecule.
22
The D,L system

is
2. Look for the highest numbered
chiral center, in this case, carbon #3
(indicated here by the highlight).
This will be used to determine D and
L configuration.
23
The D,L system

is
3. If the -OH group attached on the
highest numbered chiral center is on
the left side, you use the L
designation. Inversely, if the -OH
group at the highest numbered
chiral center is at the right side, use
the D designation.
24
Consider this isomer of

glyceraldehyde
is
Is this L-glyceraldehyde, or D-
glyceraldehyde?
25
Consider this isomer of

glyceraldehyde
is
The -OH attached at the only chiral

center in this glyceraldehyde is at
Left the left side, therefore, this is an L-
glyceraldehyde.
26
Let's have more examples

is
27
Classify the following as either L

monosaccharide or D monosaccharide
is
28

is
D monosaccharide
Solution: The highest-numbered chiral

center, which involves carnbon 4, has
the -OH group on the right. Thus, this
monosaccharide is a D
monosaccharide.
29

is
30

is
L monosaccharide
Solution: The highest-numbered chiral

center, which involves carnbon 5, has
the -OH group on the left. Thus this
monosaccharide is an L
monosaccharide.
31
But how different are the L

and D versions of the same
compound?
is
32
Let's take the hormone

epinephrine as an example
is
This medication is used in emergencies to treat

very serious allergic reactions to insect
stings/bites, foods, drugs, or other substances.
Epinephrine works quickly to improve breathing,
stimulate the heart, raise a dropping blood
pressure, reverse hives, and reduce swelling of
the face, lips, and throat.
33
Let's take the hormone

epinephrine as an example
is
Our body's response to the forms of the

hormone epinephrine (adrenaline) is very
different. The response of our body to the D
isomer of the hormone is 20 times greater than
its response to the L isomer of the hormone.
34
Epinephrine binds to its cellular receptor site by means of a three-point contact, as shown in the figure
below. D-epinephrine makes a perfect 3-point contact with the receptor surface, but the biochemically
weaker L-epinephrine can make only a 2-point contact. Because of the pooer fit, the binding of the L-
isomer is weaker, and less physiological response is observed.
35

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Designating Handedness Using Fischer Formulas

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Presentation by Nourelle M.

Fischer A Fischer projection or Fischer projection

what for? absolute configuration, at chiral centers.

Used to represent a 3D object using a 2D image.

In a Fischer projection formula, a chiral center is

Fischer The remaining discussions in this section

Projection involves drawing Fischer projection formulas to

The intersection of the vertical and horizontal lines

*Attachments on the chiral center (also called the

Let's have another

D and L, what do they

D and L, what do they mean?

How do the D,L system help us

The D,L system

To designate the handedness of a

The D,L system

The D,L system

The D,L system

Consider this isomer of

Consider this isomer of

The -OH attached at the only chiral

Let's have more examples

Classify the following as either L

Classify the following as either L

Solution: The highest-numbered chiral

Classify the following as either L

Classify the following as either L

Solution: The highest-numbered chiral

But how different are the L

Let's take the hormone

This medication is used in emergencies to treat

Let's take the hormone

Our body's response to the forms of the

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