Monosaccharides

MONOSACCHARIDES
FISCHER PROJECTION
D,L MONOSACCHARIDES
MONOSACCHARIDE STRUCTURES
FISCHER PROJECTION FORMULA
❑ was first used by the German Chemist Hermann
Emil Fischer.
❑ FISCHER PROJECTION FORMULA – is a two
dimensional structural notation for showing the
spatial arrangement of groups about chiral centers
in molecules.
https://www.sparknotes.com/chemistry/organic3/stereochemistry/section1/
FISCHER PROJECTION FORMULA
❑The Fischer Projection represents every
stereocenter as a cross. The horizontal line
represents bonds extending out of the plane of the
page, whereas the vertical line represents bonds
extending into the plane of the page.
FISHER PROJECTION
FORMULA
In Fischer projection formula, a chiral center is represented as the

intersection of the vertical and horizontal lines. The atoms in the
center is almost always the Carbon.
D,L Monosaccharides
• The simplest monosaccharide, Glyceraldehyde is considered as
a reference compound and it exists in two optically active forms,
D and L.
• The two families of monosaccharides, D-and L occur based on
the configuration of D and L glyceraldehydes.
• In general, the D-family of sugars occur in nature.
• If the hydroxyl group on the penultimate carbon is on the right-
hand side of the carbon chain when the aldehyde or ketone
group is written at the top of the formula it belongs to the D
family and if on the left hand side it belongs to L family.
D,L Monosaccharides
According to the conventions proposed by Fischer
❑D-monosaccharide: a monosaccharide that, when
written as a Fischer projection, has the -OH on its
penultimate carbon on the right (OH to the right)
❑L-monosaccharide: a monosaccharide that, when
written as a Fischer projection, has the -OH on its
penultimate carbon on the left (OH to the left)
D,L Monosaccharides
To determine whether a given enantiomer of a chiral
monosaccharide is D or L, use the following procedure.
• Step 1: Make sure the acyclic form of the molecule is drawn as

a Fischer projection. If the monosaccharide is an aldose, the
aldehyde group must be on top; if it is a ketose, the carbonyl
carbon must be the second carbon from the top.
STEP 2
• Number the carbon atoms starting at the top.
STEP 3
• Locate the carbon atom that bears the second highest number,
which is known as the penultimate carbon.
• If the hydroxy group on the penultimate carbon is on the right of
the carbon chain, assign the label D to the compound; if it is on
the left of the carbon chain, assign the label L.
STEREOISOMERS
• Isomers that differ only in the spatial orientation of their component atoms are
called stereoisomers.
• As chemists studied organic compounds isolated from plants and animals, a new and subtle type of
configurational stereoisomerism was discovered.
• For example, lactic acid ( a C3H6O3 carboxylic acid) was found in sour milk as well as in the blood
and muscle fluids of animals.
• The physical properties of this simple compound were identical, regardless of the source but there
was evidence that the physiological behavior of the compound from the two sources was not the
same.
• Other examples of this kind were encountered, and suspicions of a subtle kind of stereoisomerism
were confirmed by the different interaction these compounds displayed with plane polarized light.
• Isomeric pairs of this kind are termed enantiomers (from the Greek enantion meaning opposite).
• Enantiomers are a pair of molecules that exist in two forms that are mirror images of one another
but cannot be superimposed one upon the other.
STEREOISOMERS
Enantiomers
❑A special type of isomerism
is found in the pairs of
structures that are mirror
images of each other that are
non- super imposable.
❑This pair are designated as
D- & L-sugar.
❑Vast majority of sugars in
humans are D-sugars
Stereoisometry, DEXTRO AND LEVO
• The four bonds of the central (alpha) carbon (C) of an amino acid are directed towards the four corners of
a tetrahedron. With respect to the carboxyl (COOH) and amino (NH2) groups, there are two possible
arrangements of the H and Radical group.
• These arrangement are literally mirror images of each other, and are called stereoisomers (enantiomers).
Stereoisomers are designated D (dextro-rotatory) or L (levo-rotatory) according to the direction in which the
crystalline forms rotate polarized light, to the right and left, respectively.
• In this example, Alanine has a CH3 as a radical group. If you imagine holding the model with the COOH at the
top and the NH2 at the bottom, the CH3 radical group in the D form will be on your right. In the mirror
image L form, it will be on the left.
Optical Activity
• Identifying and distinguishing enantiomers is inherently difficult, since their
physical and chemical properties are largely identical.
• Fortunately, a nearly two hundred year old discovery by the French physicist
Jean-Baptiste Biot has made this task much easier.
• This discovery disclosed that the right- and left-handed enantiomers of a chiral
compound perturb plane-polarized light in opposite ways.
• This perturbation (disturbance of motion or course) is unique to chiral molecules,
and has been termed optical activity.
• Plane-polarized light is created by passing ordinary light through a polarizing
device, which may be as simple as a lens taken from polarizing sun-glasses.
• Such devices transmit selectively only that component of a light beam having
electrical and magnetic field vectors oscillating in a single plane. The plane of
polarization can be determined by an instrument called a polarimeter, shown in
the diagram.
Optical Activity
• Polarize means to restrict the vibrations of (a transverse
wave, especially light) wholly or partially to one
direction. • In the illustration, the sample has rotated the
polarization plane clockwise by +90º
• Monochromatic (single wavelength) light, is polarized by
a fixed polarizer next to the light source. A sample cell
holder is located in line with the light beam, followed by
a movable polarizer (the analyzer) and an eyepiece
through which the light intensity can be observed. In
modern instruments an electronic light detector takes
the place of the human eye.
• Chemists use polarimeters to investigate the influence
of compounds (in the sample cell) on plane polarized
light. If a single enantiomer is examined (all sample
molecules being right-handed, or all being left-handed),
the plane of polarization is rotated in either a clockwise
(positive) or counter-clockwise (negative) direction.
• The observed rotations (α) of enantiomers are opposite
in direction. One enantiomer will rotate polarized light in
a clockwise direction, termed dextrorotatory or (+), and
its mirror-image partner in a counter-clockwise manner,
termed levorotatory or (–).
• The prefixes dextro and levo come from the
Latin dexter, meaning right, and laevus, for left, and are
abbreviated d and l respectively.
❑one of two stereoisomers that
are mirror images of each other
that are non-superimposable
(not identical)
❑Latin (D) DEXTRO and (L)
LEVO, right and left
https://chem.libretexts.org/Courses/Purdue/Purdue%3A_Chem_26200%3A_Organic_Chemistry_II_(Wenthold)/Chapter_22._Carbohydrates/2 2.03%3A_The_D_and_L_Notation#:~:text=%2DIngold)%20method.-
,Background%20of%20D%2FL%20notation,small%20caps%20in%20published%20work).
D and L Isomers
• Certain chemicals have the capacity to rotate plane
polarised light either clockwise or counterclockwise
(anticlockwise).
• These chemicals are referred to as optically active
substances, and optical activity is the characteristic
that it possesses.
• Dextrorotatory isomer (Latin: dexter = right) or d-
form or represented by a +ve sign is the optical
isomer that spins plane polarised light to the right
(clockwise).
• Laevorotatory isomer, often known as I-form or
denoted by the -ve sign, is the optical isomer that
spins plane polarised light to the left (anticlockwise).
• Glucose, which shows optical isomers and that
if (OH) is on the right side is called D Configuration.
• And similarly, on which (OH) is left side is called L
Configuration.
Monosaccharides :TRIOSE
❑A triose is
a monosaccharide, or
simple sugar, containing
three carbon atoms.
❑Fisher projection: D-Glyceraldehyde Dihydroxyacetone
aldotriose and ketotriose
Monosaccharides :TRIOSE
Monosaccharides: Tetrose
❑A tetrose is a monosaccharide
with 4 carbon atoms.
❑they have either an aldehyde
functional group in position 1
(aldotetroses) or a ketone
functional group in position 2
(ketotetroses).
❑They have either an aldehyde functional group in
position 1 (aldotetroses) or a ketone functional group in
position 2 (ketotetroses).
(Ketotetroses).
(Aldotetroses)
Monosaccharides: Pentose
❑Pentoses are monosaccharide molecules
with five carbon atoms.
❑Pentoses can also be further divided
into two groups as aldopentoses and
ketopentoses.
❑Ribose, xylose, arabinose,
lyxose, are aldopentoses.
❑ Ribulose, xylulose are ketopentoses
Aldopentoses
Ketopentoses
Monosaccharides: HEXOSES
Hexoses- A sugar or saccharide containing
six carbon
KETOHEXOSES ALDOHEXOSES
❑psicose ❑ allose ❑ gulose
❑fructose ❑ altrose ❑ idose
❑sorbose ❑ glucose ❑ galactose
❑Tagatose ❑ mannose ❑ talose
KETOHEXOSES STRUCTURES
ALDOHEXOSES STRUCTURES
ALDOHEXOSES STRUCTURES

Monosaccharides

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MONOSACCHARIDES

In Fischer projection formula, a chiral center is represented as the

• Step 1: Make sure the acyclic form of the molecule is drawn as

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