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NEWSLETTER 8 - Extension 1 : The Great Variety of Saccharides
(Updated September 2005)
Introduction
Prototype
Properties
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A Prototype for the Saccharide Molecule
Saccharides, also known as carbohydrates, are organic molecules containing carbon, oxygen, and hydrogen
atoms. Saccharides have a sweet taste.
Our prototype of a saccharide -- the glucose molecule -- contains six atoms of carbon, six of oxygen and
twelve of hydrogen.
To illustrate molecules, chemists use different formulations.
The Empirical Formulation
The empirical formulation of a molecule only indicates the atoms involved and their numbers. The empirical
formulation of a glucose molecule comes like this : C6O6H12
The Projection Formulation
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Another way to illustrate a molecule -- the projection formulation -- simulates the orientation of the
atomic constituents of the molecule in space. Since the three dimensional orientation of a molecule
governs its chemical properties, the projection formulation contains more information about the
molecule.
The projection formulation is rather hard to decipher, and we shall use a more visual presentation of the
prototype saccharide molecule for our demonstration.
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A Visual Presentation
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The spine of a glucose molecule is formed of 6 carbon atoms
-- illustrated here as blue-black spheres -- in a vertical
straight row. (Saccharides share their central carbon row
with proteins and lipids. Human life and life on earth are
organized around a carbon spine)
The glucose molecule also contains 6 atoms of oxygen -- red -- and 12 atoms of hydrogen -- white.
A biochemist would immediately react to this presentation by telling you that the carbon atoms in a
saccharide molecule do not come in a straight line, but in a broken line with well defined angles
between each of them.
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The chemist may add that saccharides not always come in a (broken)
line, that they also exist in a closed (circular) line where the
first carbon is linked -- with an oxygen atom between them -- to
another carbon of the molecule. Both remarks are correct.
We shall overlook the broken line and the closed configuration because we don't need it for our
demonstration.
Glucose vs. Mannose
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Look at the above illustration of the glucose molecule and
compare its structure to that of another saccharide molecule
-- the mannose molecule -- which is illustrated to the right
of this text.
As you can see, the two molecules have an identical composition of 6 carbon (blue-black), 6 oxygen (red),
and 12 hydrogen (white) atoms.
At closer look the difference between the two molecules appears. The mannose molecule has its second
atom of carbon -- starting from the top of the molecule -- and the adjacent hydrogen and oxygen atoms
rotated 180 degrees as compared to their orientation in the glucose molecule.
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Properties : Diversity, Terminology, and Complexity of Saccharide Molecules
Diversity
The difference between the glucose and the mannose molecule is the orientation of one of the asymmetrical
structures the molecules contain. There are four such asymmetrical structures in glucose and in mannose.
A consequence of it is that there are theoretically as much as sixteen different combinations of asymmetric group
orientations possible. Each of these 16 combinations is a molecule with different chemical properties.
Now consider that a typical saccharide has up to four sites (handles) to grasp another saccahride.
The number of possible combination of saccharides is much larger than the number of combination of
amino-acids. Indeed, an amino acids has only two handles to form proteins (Table 1).
| Number of Molecules |
Number of Combinations for Amino-acids |
Number of Combinations for Saccharides |
| 2 |
4 |
16 |
| 3 |
8 |
64 |
| 16 |
64 |
256 |
Table 1: The number of combinations for a saccharide is greater than
for an amino acid.
Terminology
Saccharides with six carbons are termed hexose (from the Greek word "hex" for six). Glucose and mannose
are hexoses. There are saccharides with less than six carbons. A saccharide with five carbons is a
pentose (Greek penta = five), with four it is a tetrose (tetra = four), with three a triose (tres).
Pyruvic acid is a triose. Pentoses form the spine of our chromosomes.
Complexity
Before going any further, we have to become familiar with four new terms: "monosaccharide",
"disaccharide", "oligosaccharide", and "polysaccharide".
A monosaccharide is a molecule with six or less carbon atoms.
A disaccharide contains two monosaccharides.
An oligosaccharide contains more than two and up to six monosaccharides.
A polysaccharide is a more complex molecule formed from more than six monosaccharides.
Monosaccharides form polysaccharides by attaching to each other in long sequences. That attachement is
termed polymerization and the obtained complex molecule is a polymer. Polymerization is an enzymatic
process.
In animals -- humans included -- such polymerization of the monosaccharide glucose produces glycogen.
Glycogen is an ramified polymer. Glycogen is the storage form of glucose.
Chondroitine -- the basic substance of bones and cartilage -- is a polymer of glucose and glucosamine.
(Glucosamine is a molecule of glucose with a nitrogen atom added)
In plants the polymerization of saccharides produces cellulose, in insects, crustacea and other organisms
the polymerization of saccharides results in the production of chitin. Chitin is a polymer of
glucosamine.
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