Elham M .

Al-Khashab, BSc, MSc, PhD,(Biochemistry)

Assistant professor , Department of Physiology, Biochemistry, and Pharmacology
College of Veterinary Medicine, University of Mosul, Mosul, Iraq
https://orcid.org/ 0000-0002-9180-2790
https://www.researchgate.net/profile/ Elham M .Al-khashab

Biochemistry | Part Π| 1styear 2019-2020

Carbohydrates

Definition:-
Carbohydrates may be defined chemically as aldehyde or ketone derivatives of polyhydroxy alcohols or as
compounds that yield these derivatives on hydrolysis
Carbohydrates are
• A major source of energy from our diet.
• Composed of the elements C, H, and O.
• Also called saccharides, which means “sugars.”
• Carbohydrates are produced by photosynthesis in plants.
glucose is synthesized in plants from CO2, H2O, and energy from the sun then oxidized in living

cells (respiration) to produce CO2, H2O, and energy.

Functions of Carbohydrates:
1 - Source of energy for living beings, e.g. glucose
2 - Storage form of energy, e.g. glycogen in animal tissue and starch in plants
3 - Serve as structural component, e.g. glycosaminoglycans in humans, cellulose in plants and
chitin in insects
4 - Non-digestable carbohydrates like cellulose, serve as dietary fibers
5 - Constituent of nucleic acids RNA and DNA, e.g. ribose and deoxyribose sugar
6 - Play a role in lubrication, cellular intercommunication and immunity
7 - Carbohydrates are also involved in detoxification, e.g. glucuronic acid

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Classification of Carbohydrates
Carbohydrates are classified into three groups:

1. Monosaccharides=single unit
2. Oligosaccharides =2-10 units
3. Polysaccharides >10 units
The suffix ose indicates that a molecule is a carbohydrate .e.g maltose, glucose, lactose,
fructose ,ribose
Monosaccharides (Greek: Mono = one)
• Monosaccharides are also called simple sugars. The term sugar is applied to
carbohydrates that are soluble in water and sweet to taste
• They consist of a single unit
• polyhydroxy aldehyde or ketone unit, and thus cannot be hydrolyzed into a
simpler form.

Monosaccharides may be subdivided into two groups as follows:

1. Depending upon the number of carbon atoms they possess, e.g.
• Trioses 3 carbon Glyceraldehyde
• Tetroses 4 carbon Erythrose
• Pentoses 5 carbon Ribose, Xylose
• Hexoses 6 carbon Glucose, Galactose, fructose
• Heptoses. 7 carbon Glucoheptos

2. Depending upon the functional aldehyde (CHO) or ketone (C=O) group

present:
• Aldoses CHO Glucose, Galactose
 Ketoses C=O Fructose

ALDOSES:

D-ribose D-glucose D-galactose

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KETOSES:

D-ribulose D-fructose

GLUCOSE
• Physiologically and biomedically , glucose is the most important monosaccharide

• It is called blood sugar

• C6H12O6

• It is monosaccharide (aldose)

• It is source of energy

• It is produced by hydrolysis of glycogen

Anomerism
α and β Anomerism

• The predominant form of glucose and fructose in a solution are not an open chain. Rather,
the open chain form of these sugar in solution cyclize into rings. An additional asymmetric
center is created when glucose cyclizes. Carbon-1 of glucose in the open chain form,becomes
an asymmetric carbon in the ring form and two ring structures can be formed. These are:

• α-D-glucose

• β-D-glucose.

• The designation α means that the hydroxyl group attached to C-1 is below the plane of the
ring, β means that it is above the plane of the ring. The C-1 carbon is called the anomeric
carbon atom and so, α and β forms are anomers

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.When a five-membered ring is formed, it is called a furanose, shown in the figure below

D-ribose -D-ribofuransoe -D-ribofuranose

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 +

D-fructose -D-fructofuranose -D-fructofuranose

• isomerism
• Glucose and fructose are isomers of each other having the same chemical (molecular) formula C 6H12O6, but they
differ in structural formula There is a keto group in position 2 of fructose and an aldehyde group in position 1 of
glucose. This type of isomerism is known as ketose-aldose isomerism

GLYCOSIDE FORMATION: Glycosides are formed when the hydroxyl group of anomeric
carbon of a monosaccharide reacts with OH or NH group of second compound that may or
may not be a carbohydrate. The bond so formed is known as glycosidic bond.

• The monosaccharides are joined by glycosidic bonds to form disaccharides,

oligosaccharides and polysaccharides.

Phosphoric acid ester of glucose

Asymmetric carbon: Asymmetric carbon: carbon atom which attached to four(4)different

groups

D and L isomerism

D and L isomerism depends on the orientation of the H and OH groups around the
asymmetric carbon atom adjacent to the terminal primary alcohol carbon, e.g. carbon atom
number 5 in glucose determines whether the sugar belongs to D or L isomer.

• When OH group on this carbon atom is on the right, it belongs to D-series, when it is on the
left, it is the member of the L-series.

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• The structures of D and Lglucose based on the reference monosaccharide, D and L
glyceraldehyde, a three carbon sugar

D and L isomerism

Disaccharides
 Disaccharides consist of two monosaccharide units.

• They are crystalline, water soluble and sweet to taste. they are divided to:
1.Reducing disaccharides with free carbonyl group , e.g. maltose, lactose

2. Non-reducing disaccharides with no free carbonyl group, e.g. sucrose.

Maltose
• Maltose contains two glucose residues, joined by glycosidic linkage between C-1 (the
anomeric carbon) of one glucose residue and C-4 of the other ,leaving one free anomeric
carbon of the second glucose residue, which can act as a reducing agent. Thus, maltose is a
reducing disaccharide.

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• Maltose=Glucose + Glucose it is reducing sugar

Sucrose (Common Table Sugar)

• Sucrose is a disaccharide of glucose and fructose. it is formed by plant but not

by human beings. Sucrose is the commonly used table sugar. In contrast to
maltose and lactose, sucrose is non reducing sugar (why?)

becaue sucrose contains no free anomeric carbon atom the anomeric carbon
of both glucose and fructose are involved in the formation glycosidic bond.

Sucrose= Glucose + Fructose

Oligosaccharides (Greek: oligo = few)

• Oligosaccharides consist of a short chain of monosaccharide units (2 to 10 units), joined
together by a characteristic bond called glycosidic bond which, on hydrolysis, gives two to ten
molecules of simple sugar (monosaccharide) units.

Polysaccharides
• Carbohydrates composed of ten or more units of monosaccharide

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• Polysaccharides are colloidal in size. In polysaccharides, monosaccharide units
are joined together by glycosidic linkages. Another term for polysaccharides is a
“glycans Polysaccharides are subclassified in two groups :-

1. Homopolysaccharides (Homoglycans): When a polysaccharide is made up of

several units of one and the same type of monosaccharide unit only, it is called
homopolysaccharide.e.g. starch ,glycogen

2. Heteropolysaccharides (Heteroglycans): They contain two or more different

types of monosaccharide units or their derivatives. e.g.hyaluronicacid.

Starch

• It is the storage form of glucose in plants, e.g. in potato. Starch is composed

of two constituents. 1- amylose and. 2- amylopectin

Amylose is a linear polymer of D-glucose units joined by α-1 → 4 glycosidic

linkages

• Amylopectin: amylopectin is a branched polymer,it is structurally identical to

those of amylose (α-1→ 4 glycosidic linkages) but with side chains joining them
by α-1→ 6 linkages.Thus, having both α-(1 → 4) and α-(1 → 6) linkages.

• Glycogen (Animal Starch)

• Glycogen is the major storage form of carbohydrate(glucose) in animals, found

mostly in liver and muscle.

• It is often called animal starch.

• The structure of glycogen is similar to that of amylopectin, except that it is more

highly branched,

Functions of glycogen

• The function of muscle glycogen is to act as a readily available source of glucose

for energy within muscle itself.

• Liver glycogen is concerned with storage and maintenance of the blood glucose

Cellulose

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• Cellulose is the chief constituent of cell wall of plants.

• It is an unbranched polymer of glucose and consists of long straight chains which

are linked by β-(1→4) glycosidic linkages and not α-(1→ 4) as in amylase.

• Since humans lack an enzyme cellulase that can hydrolyze the β-(1→ 4)
glycosidic linkages, cellulose cannot be digested and absorbed and has no food
value unlike starch. However, the ruminants can utilize cellulose because they
have in their digestive tract microorganisms whose enzymes hydrolyze cellulose

Structure of cellulose

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