Presentation by Nourelle M.
Calam
Designating
Handedness Using
Fischer Projection
Formulas
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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.
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
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
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
Fischer Projection
Formulas for
Monosaccharides
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
Consider Glyceraldehyde
The simplest
monosaccharide that has a
chiral center is the 3-
carbon polyhydroxy
aldehyde Glyceraldehyde
(2,3-dihydroxypropanal)
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Presentation by Nourelle M. Calam
Consider Glyceraldehyde
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Presentation by Nourelle M. Calam
Consider Glyceraldehyde
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.
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Presentation by Nourelle M. Calam
Consider Glyceraldehyde
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Presentation by Nourelle M. Calam
The intersection of the vertical and horizontal lines
indicate the presence of a chiral center.
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Presentation by Nourelle M. Calam
*Attachments on the chiral center (also called the
stereocenter) can be interchanged, leaving you with two
isomers of this compound.
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Presentation by Nourelle M. Calam
Let's have another
example
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Presentation by Nourelle M. Calam
2,3,4-trihydroxybutanal
is
is a monosaccharide with 4
carbons and two chiral centers
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Presentation by Nourelle M. Calam
2,3,4-trihydroxybutanal
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
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Presentation by Nourelle M. Calam
2,3,4-trihydroxybutanal
is
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Presentation by Nourelle M. Calam
D and L, what do they
mean?
is
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
How do the D,L system help us
identify which is which?
is
here's how
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Presentation by Nourelle M. Calam
The D,L system
is
To designate the handedness of a
monosaccharide with one or more than chiral
center, we follow these steps:
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Start
Presentation by Nourelle M. Calam
counting
here!
The D,L system
is 1. The carbon chain is numbered
starting at the carbonyl group
end of the molecule.
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
Consider this isomer of
glyceraldehyde
is
Is this L-glyceraldehyde, or D-
glyceraldehyde?
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
Let's have more examples
is
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Presentation by Nourelle M. Calam
Classify the following as either L
monosaccharide or D monosaccharide
is
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Presentation by Nourelle M. Calam
Classify the following as either L
monosaccharide or D monosaccharide
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.
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Presentation by Nourelle M. Calam
Classify the following as either L
monosaccharide or D monosaccharide
is
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Presentation by Nourelle M. Calam
Classify the following as either L
monosaccharide or D monosaccharide
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.
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Presentation by Nourelle M. Calam
But how different are the L
and D versions of the same
compound?
is
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
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.
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Presentation by Nourelle M. Calam
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.
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