Carbohydrates- definition, structure, types, examples, functions

What are carbohydrates

 The carbohydrates are a group of naturally occurring carbonyl compounds
(aldehydes or ketones) that also contain several hydroxyl groups.
 It may also include their derivatives which produce such compounds on hydrolysis.
 They are the most abundant organic molecules in nature and also referred to as
“saccharides”.
 The carbohydrates which are soluble in water and sweet in taste are called as
“sugars”.
Structure of Carbohydrates
 Carbohydrates consist of carbon, hydrogen, and oxygen.
 The general empirical structure for carbohydrates is (CH2O)n.
 They are organic compounds organized in the form of aldehydes or ketones with
multiple hydroxyl groups coming off the carbon chain.
 The building blocks of all carbohydrates are simple sugars called monosaccharides.
 A monosaccharide can be a polyhydroxy aldehyde (aldose) or a polyhydroxy ketone
(ketose).

KETOSE ALDOSE ALDOSE

The carbohydrates can be structurally represented in any of the three forms:

 Open chain structure.
 Hemi-acetal structure.
 Haworth structure.
Open chain structure – It is the long straight-chain form of carbohydrates.
Hemi-acetal structure – Here the 1st carbon of the glucose condenses with the -OH group of
the 5th carbon to form a ring structure.
Haworth structure – It is the presence of the pyranose ring structure.

Properties of Carbohydrates
Physical Properties of Carbohydrates
 Stereoisomerism – Compound shaving the same structural formula but they differ in
spatial configuration. Example: Glucose has two isomers with respect to the
penultimate carbon atom. They are D-glucose and L-glucose.
 Optical Activity – It is the rotation of plane-polarized light forming (+) glucose and
(-) glucose.
  Diastereo isomers – It the configurational changes with regard to C2, C3, or C4 in
glucose. Example: Mannose, galactose.
 Annomerism – It is the spatial configuration with respect to the first carbon atom in
aldoses and second carbon atom in ketoses.
Properties of Monosaccharides
 Most monosaccharides have a sweet taste (fructose is sweetest; 73% sweeter than
sucrose).
 They are solids at room temperature.
 They are extremely soluble in water: – Despite their high molecular weights, the
presence of large numbers of OH groups make the monosaccharides much more
water-soluble than most molecules of similar MW.
 Glucose can dissolve in minute amounts of water to make a syrup (1 g / 1 ml H2O).

Classification of Carbohydrates (Types of Carbohydrates)

The simple carbohydrates include single sugars (monosaccharides) and polymers,

oligosaccharides, and polysaccharides.
Monosaccharides
 Simplest group of carbohydrates and often called simple sugars since they cannot be
further hydrolyzed.
 Colorless, crystalline solid which are soluble in water and insoluble in a non-polar
solvent.
 These are compound which possesses a free aldehyde or ketone group.
 The general formula is Cn(H2O)nor CnH2nOn.
 They are classified according to the number of carbon atoms they contain and also on
the basis of the functional group present.
 The monosaccharides thus with 3,4,5,6,7… carbons are called trioses, tetroses,
pentoses, hexoses, heptoses, etc., and also as aldoses or ketoses depending upon
whether they contain aldehyde or ketone group.
 Examples: Glucose, Fructose, Erythrulose, Ribulose.
Oligosaccharides
 Oligosaccharides are compound sugars that yield 2 to 10 molecules of the same or
different monosaccharides on hydrolysis.
 The monosaccharide units are joined by glycosidic linkage.
 Based on the number of monosaccharide units, it is further classified as disaccharide,
trisaccharide, tetrasaccharide etc.
  Oligosaccharides yielding 2 molecules of monosaccharides on hydrolysis is known
as a disaccharide, and the ones yielding 3 or 4 monosaccharides are known as
trisaccharides and tetrasaccharides respectively and so on.
 The general formula of disaccharides is Cn(H2O)n-1and that of trisaccharides is
Cn(H2O)n-2 and so on.
 Examples: Disaccharides include sucrose, lactose, maltose, etc.
 Trisaccharides are Raffinose, Rabinose.
Polysaccharides
 They are also called as “glycans”.
 Polysaccharides contain more than 10 monosaccharide units and can be hundreds of
sugar units in length.
 They yield more than 10 molecules of monosaccharides on hydrolysis.
 Polysaccharides differ from each other in the identity of their recurring
monosaccharide units, in the length of their chains, in the types of bonds linking
units and in the degree of branching.
 They are primarily concerned with two important functions ie. Structural functions
and the storage of energy.
 They’re further classified depending on the type of molecules produced as a result of
hydrolysis.
 They may be homopolysaccharidesL, containing monosaccharides of the same type
or heteropolysaccharides i.e., monosaccharides of different types.
 Examples of Homopolysaccharides are starch, glycogen, cellulose, pectin.
 Heteropolysaccharides are Hyaluronic acid, Chondroitin.

Functions
Carbohydrates are widely distributed molecules in plant and animal tissues. In plants and
arthropods, carbohydrates from the skeletal structures, they also serve as food reserves in plants
and animals. They are important energy source required for various metabolic activities; the
energy is derived by oxidation.
Some of their major functions include:
 Living organisms use carbohydrates as accessible energy to fuel cellular reactions.
They are the most abundant dietary source of energy (4kcal/gram) for all living
beings.
 Carbohydrates along with being the chief energy source, in many animals, are instant
sources of energy. Glucose is broken down by glycolysis/ Kreb’s cycle to yield ATP.
 Serve as energy stores, fuels, and metabolic intermediates. It is stored as glycogen in
animals and starch in plants.
 Stored carbohydrates act as an energy source instead of proteins.
 They form structural and protective components, like in the cell wall of plants and
microorganisms. Structural elements in the cell walls of bacteria (peptidoglycan or
murein), plants (cellulose) and animals (chitin).
 Carbohydrates are intermediates in the biosynthesis of fats and proteins.
 Carbohydrates aid in the regulation of nerve tissue and is the energy source for the
brain.
  Carbohydrates get associated with lipids and proteins to form surface antigens,
receptor molecules, vitamins, and antibiotics.
 Formation of the structural framework of RNA and DNA (ribonucleic acid and
deoxyribonucleic acid).
 They are linked to many proteins and lipids. Such linked carbohydrates are important
in cell-cell communication and in interactions between cells and other elements in
the cellular environment.
 In animals, they are an important constituent of connective tissues.
 Carbohydrates that are rich in fiber content help to prevent constipation.
 Also, they help in the modulation of the immune system

Epimers
All the stereogenic centers are inverted when comparing D and L isomers since they
are enantiomers and any other pair of stereoisomers represents diastereomers. For example,
while the D and L-Glucoses are enantiomers, D-Glucose and D-mannose are
diastereomers since the configuration of only one stereogenic center (C2) is changed:
Diastereomers that differ in the configuration of only one chiral center are called epimers. Of
course, there should be more than one chiral center, otherwise, the change of one would
indicate a pair of enantiomers.
So, D-Glucose and D-mannose are epimers and to specify, they are epimeric at carbon-2.
On the other hand, D-glucose and D-galactose are epimeric at carbon-4 since that is the only
stereogenic center with an opposite configuration:

Anomers
Carbohydrates exist also in a cyclic form and this is especially favored when 5- 6-membered
rings can be formed. These rings are classified as a furanose and a pyranose ring respectively
which is a general nomenclature for oxygen-containing 5– 6-membered rings.
They are formed through an intramolecular hemiacetal formation. For example, the linear D-
Glucose converts into a pyranose ring through the attack of C5-OH group on the carbonyl
forming a new asymmetric center. Interestingly, this new asymmetric center is formed in both
configurations:

Carbon 1 is the new stereogenic center shown with a wiggly line which means the formation of
both configurations.

Now, the structure on the right is the cyclic form of D-Glucose which, as a six-membered ring
adopts a chair conformation. I know that it is not evident that these two structures represent the
same molecule, but for now, take it as a fact, and we will describe this process for converting
between Fischer, Haworth, and Chair forms of Glucose in the next post.
Notice that all the initial chiral centers remain intact, and the two cyclic forms differ in the
configuration of only one chiral center. We classify these as epimers, and in the case of sugars,
they are said to be anomers. So, an anomer is type of epimer characterized by the carbon in
two possible configurations of a cyclic saccharide.
This carbon is called the anomeric carbon (carbon 1 in the picture above) and the configuration
about it is denoted by prefixes ɑ – and β.

If the newly formed OH group on the asymmetric center is pointing down (trans to CH2OH
group at C-5), then it is ɑ-D-glucose. On the other hand, if the OH group is pointing up (cis to
the CH2OH group at C-5), then the hemiacetal is β-D-glucose.

Keep in mind that “up” and “down” is always ambiguous unless we specify what it is relative to.
For example, if we flip the chairs 180o (not a ring-flip), all the “up” and “down” notation will
change. That is why the cis and trans orientation of the Oh group to the CH2OH on carbon 5 is
emphasized.
One statement that is true regardless of the way we draw the chair is that all the OH groups
in β -D-glucose are equatorial.