Module in Biochemistry

MODULE 2. CARBOHYDRATES

Overview:

Carbohydrates represent a broad group of substances which include the sugars,

starches, gums and celluloses. The common attributes of carbohydrates are that they
contain only the elements carbon, hydrogen and oxygen, and that their combustion will
yield carbon dioxide plus one or more molecules of Water.

Learning Outcomes:

1. Define carbohydrates

2. Enumerate and discuss the classification of carbohydrates

3. Discuss the importance of carbohydrates

Discussion:

Carbohydrate, class of naturally occurring compounds and derivatives formed

from them. In the early part of the 19th century, substances such as wood, starch,
and linen were found to be composed mainly of molecules
containing atoms of carbon (C), hydrogen (H), and oxygen (O) and to have the general
formula C6H12O6; other organic molecules with similar formulas were found to have a
similar ratio of hydrogen to oxygen. The general formula Cx(H2O)y is commonly used to
represent many carbohydrates, which means “watered carbon.”
Carbohydrates (glycans) have the following basic composition:

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 The term carbohydrate is derived from the french: hydrate de carbone

 compounds composed of C, H, and O
 empirical formula: (CH2O)n
 Most carbohydrates are found naturally in bound form rather than as simple sugars
 Polysaccharides (starch, cellulose, inulin, gums)
 Glycoproteins and proteoglycans (hormones, blood group substances,
antibodies)
 Glycolipids (cerebrosides, gangliosides)
 Glycosides
 Mucopolysaccharides (hyaluronic acid)
 Nucleic acids

Functions of Carbohydrates
1. sources of energy
2. intermediates in the biosynthesis of other basic biochemical entities (fats and
proteins)
3. associated with other entities such as glycosides, vitamins and antibiotics)
4. form structural tissues in plants and in microorganisms (cellulose, lignin, murein)
5. participate in biological transport, cell-cell recognition, activation of growth
factors, modulation of the immune system

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Classification of carbohydrates
A. Number of Carbohydrate Units

1. Monosaccharides - simple sugars with multiple OH groups. Based on number of

carbons (3, 4, 5, 6, 7), a monosaccharide is a triose, tetrose, pentose, hexose or
heptose
2. Disaccharides - 2 monosaccharides covalently linked.
3. Oligosaccharides - a few monosaccharides covalently linked.
4. Polysaccharides - polymers consisting of chains of monosaccharide or
disaccharide units.
B. Position of carbonyl group
at C1, carbonyl is an aldehyde: aldose
at any other carbon, carbonyl is a ketone: ketose

C. Number of carbons
Triose – three carbons Hexose – six carbons
Tetrose – four carbons Heptose – seven carbons
Pentose – five carbons

D. Cyclic form

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Monosaccharides

Carbonyl Group – is a carbon atom double bonded to an oxygen atom.

C O

Aldehydes - one of the two additional bonds that the carbonyl carbon atom forms must
be to a hydrogen atom.

H C H

Aldoses (e.g., glucose) have an aldehyde group at one end

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carbohydrates

Ketones – both of the additional bonds of the carbonyl carbon atom must be to another
carbon atom that is part of alkyl, cycloalkyl, or aromatic group.

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C C C

Ketoses (e.g., fructose) have a keto group, usually at C2.

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carbohydrates

Dextrorotatory and Levorotatory Designation

Carbohydrates are designated as D- or L- according to the stereochemistry of

the highest numbered chiral carbon of the Fischer projection. If the hydroxyl group of
the highest numbered chiral carbon is pointing to the right, the sugar is designated as D
(Dextro: Latin for on the right side). If the hydroxyl group is pointing to the left, the sugar
is designated as L (Levo: Latin for on the left side). Most naturally occurring
carbohydrates are of the D-configuration.

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Sugar Nomenclature

For sugars with more than one chiral center, D or L refers to the asymmetric C
farthest from the aldehyde or keto group.

Chiral Center – an atom in a molecule that has four different groups bonded to it
in a tetrahedral orientation.

Most naturally occurring sugars are D isomers.

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carbohydrates

D & L sugars are mirror images of one another. They have the same name, e.g.,
D-glucose & L-glucose.

Other stereoisomers have unique names, e.g., glucose, mannose, galactose, etc.

The number of stereoisomers is 2n, where n is the number of asymmetric

centers.

The 6-C aldoses have 4 asymmetric centers. Thus there are 16 stereoisomers (8
D-sugars and 8 L-sugars).

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Hemiacetal & hemiketal formation

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carbohydrates

Pentoses and hexoses can cyclize as the ketone or aldehyde reacts with a distal
OH.

Glucose forms an intra-molecular hemiacetal, as the C1 aldehyde & C5 OH react, to

form a 6-member pyranose ring, named after pyran. These representations of the cyclic
sugars are called Haworth projections.

Haworth Projections – a two- dimensional structural notation that specifies the three-
dimensional structure of a cyclic form of a monosaccharide.

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Fructose forms either

 a 6-member pyranose ring, by reaction of the C2 keto group with the OH on C6,
or

 a 5-member furanose ring, by reaction of the C2 keto group with the OH on C5.

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carbohydrates

Cyclization of glucose produces a new asymmetric center at C1. The 2

stereoisomers are called anomers, a & b.

Haworth projections represent the cyclic sugars as having essentially planar

rings, with the OH at the anomeric C1:

 a (OH below the ring)

 b (OH above the ring).

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Because of the tetrahedral nature of carbon bonds, pyranose sugars actually

assume a "chair" or "boat" configuration, depending on the sugar.

The representation above reflects the chair configuration of the glucopyranose ring
more accurately than the Haworth projection.

Disaccharides

 Lactose: glucose + galactose

 Maltose: glucose + glucose

 Sucrose: glucose + fructose

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Condensation to form Disaccharides

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Importance of Disaccharide

 Energy storage: sucrose is a store of energy in sugarcane and sugar beets

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 Energy transport: carbohydrate is transported in plants as sucrose

Examples of Disaccharides

1. Maltose

Formed from 2 glucose molecules, formed in germinating seeds from the

breakdown of starch, providing energy.

2. Sucrose

Formed from 1 glucose and 1 fructose molecule and is the form in which
carbohydrates are transported in the phloem in plant.

3. Lactose

Formed from 1 glucose and 1 galactose molecule, it is an energy source found in

the milk of nearly all mammals.

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Polysaccharides

Carbohydrates which are made from many linked monosaccharide monomers

form long chain-like molecules called polymers.

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Starch

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carbohydrates

 Made of α glucose molecules linked by glycosidic bonds.

 Used as an energy store in plants.

 Not soluble.

 Forms solid grains inside plant cells (often inside chloroplasts).

 The chains coil up into a basic spiral shape making the molecules compact.

 Hydrogen bonds hold the polysaccharide chain in the compact spiral shape.

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Glycogen

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carbohydrates

 This is the storage polysaccharide in animals

(equivalent to starch in plants).
 Found in liver and muscle cells where a store of energy is needed.
 Many fungi also store glycogen.
 Similar in structure to starch - but more branched.
 Forms tiny granules inside cells which are usually associated with smooth
endoplasmic reticulum.
 Each glycogen molecule contains a few 1000 glucose units.
Cellulose

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 Most abundant organic molecule.

 It is very slow to decompose.

 20-40% of the plant cell wall.

 Made of β glucose units.
 Every other β glucose is rotated through 180° - this makes the chains straight, not
coiled.
 Hydrogen bonding between monosaccharide molecules in the chain gives strength.
 Hydrogen bonding between cellulose molecules cause bundles called microfibrils to
develop. These are held together in fibres.
 A cell wall will have several layers of fibres running in different directions - gives
great strength almost equal to steel.
 Provides support in plants and stops plant cells bursting.
 Freely permeable to water and solutes.
Hydrolysis- breaking of disaccharide or polysaccharide to form monosaccharide
with the addition of water.

Dehydration synthesis – combination of two monosaccharide molecules to form

dissacharide or polysaccharide that leads to the removal of water.

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carbohydrates

Role in human nutrition

The total caloric, or energy, requirement for an individual depends on age,

occupation, and other factors but generally ranges between 2,000 and
4,000 calories per 24-hour period (one calorie, as this term is used in nutrition, is the
amount of heat necessary to raise the temperature of 1,000 grams of water from 15 to
16 °C [59 to 61 °F]; in other contexts this amount of heat is called the kilocalorie).
Carbohydrate that can be used by humans produces four calories per gram as opposed
to nine calories per gram of fat and four per gram of protein. In areas of the world where
nutrition is marginal, a high proportion (approximately one to two pounds) of an
individual’s daily energy requirement may be supplied by carbohydrate, with most of the
remainder coming from a variety of fat sources.

Assessment:

1. What is a carbohydrate?
2. Give examples of foods that are rich in carbohydrates
3. Discuss the classification of carbohydrates
4. What are the importance of carbohydrates?

Please visit this link for additional information:

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https://www.youtube.com/watch?v=jQi84TnstI4

References:

Stoker, Stephen H. Exploring General, Organic and Biological Chemistry. 6th Edition

Campbell, Biology. 4th Edition

Manosa, S., Talaue, F. (2007). Breaking Through Biology, C & E Publishing, Inc.

https://www.britannica.com/science/carbohydrate

https://alevelbiology.co.uk/notes/carbohydrates-introduction-and-classification/

https://foodandhealth.com/5-things-to-know-carbohydrate/

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