Carbohydrates

Lecture 1
Noor Ullah
B.Sc MLT, M.Sc Biochemistry, M.Phil Biochemistry/ Mol. Biology
PhD Scholar Biochemistry
Lecturer MLT, KMU IPMS
Carbohydrates

• Carbohydrates- Carbon hydrates ( C- H20)

• Polyhydroxy aldehyde or ketones

• Many, but not all, carbohydrates have the empirical formula (C- H20)n

• Most abundant biomolecules on the earth

• Three major classes of carbohydrates:

• Monosaccharides, oligosaccharides, and polysaccharides

• (The word “saccharide” is derived from the Greek sakcharon, meaning “sugar”).

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Monosaccharides

• Monosaccharides are the simplest carbohydrates

• They are colorless, crystalline solids that are freely soluble in water but insoluble
in nonpolar solvents.

• The simplest monosaccharides are the two three-carbon trioses: glyceraldehyde

and dihydroxyacetone.

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Monosaccharides

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Monosaccharides

• Monosaccharides with four, five, six, and seven carbon atoms in their backbones
are called, respectively, tetroses, pentoses, hexoses, and heptoses.

• The D-glucose and D-fructose are the most common monosaccharides in

nature.

• The aldopentoses, D-ribose and 2-deoxy-D-ribose are components of nucleotides

and nucleic acids.

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Monosaccharides

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Asymmetric or Chiral Centers

• Carbon to which four different atoms or groups are attached is called

asymmetric.

• All the monosaccharides except dihydroxyacetone contain one or more

asymmetric (chiral) carbon atoms and thus occur in optically active isomeric
forms- Enantiomers or Mirror images.

• To represent three-dimensional sugar structures on paper, we often use Fischer

projection formulas.

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Epimers

• Two sugars that differ only in the configuration around one carbon atom are
called epimers.

• D-glucose and D-mannose, which differ only at C-2 and D-glucose and D-
galactose (which differ at C-4) .

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Epimers

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 Tautomerism 
• The process of shifting a hydrogen atom
from one carbon atom to another to
produce enediols is known as
tautomerization
• Sugars possessing anomeric carbon atom
undergo tautomerization in alkaline
solutions
• When glucose is kept in alkaline solution
for several hours, it undergoes
isomerization to form D-fructose and D-
mannose through a common
intermediate- enediol- two OH groups are
attached to the double bonded carbon

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 Hemiacetals and hemiketals

• They are formed when an alcohol oxygen

atom adds to the carbonyl carbon of an
aldehyde or a ketone.

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 Cyclization of glucose to its hemiacetal form

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 Cyclization of Glucose

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Anomers and ring structure

• Isomeric forms of monosaccharides that differ only in their configuration

about the hemiacetal or hemiketal carbon atom are called anomers, and the

carbonyl carbon atom is called the anomeric carbon.

• Pyranose is a six-membered ring with Oxygen bridge between C no.1 and 5.

• Furanose is a five-membered ring with oxygen bridge between C no.1 and 4.

• The systematic names for the two ring forms of D-glucose are therefore

alpha-D-glucopyranose and beta-D-glucopyranose.

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 Pyranose and Furanose ring structure

Pyranoses and furanoses. The pyranose forms of D-glucose and the furanose forms of D-fructose are shown
here as Haworth perspective formulas. The edges of the ring nearest the reader are represented by bold lines.
Pyran and furan are shown for comparison.
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Glycosides

• When the hydroxyl group of one monosaccharide reacts with the hydroxyl group
of another monosaccharide, it forms glycosidic linkage.

• Glycosides are compounds in which a monosaccharide is attached at the

anomeric carbon to an alcohol residue of non-carbohydrate.

• The non-carbohydrate residue is called aglycon.

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Physiologically important glycosides

1. Glucovanillin (vanillin-D-glucoside) is a natural substance that imparts vanilla

flavor.

2. Cardiac glycosides (steroidal glycosides): Digoxin and digitoxin contain the

aglycone steroid and they stimulate muscle contraction.

3. Streptomycin, an antibiotic used in the treatment of tuberculosis is a glycoside.

4. Ouabain inhibits Na+ –K+ ATPase and blocks the active transport of Na+.

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Reducing Sugars

• All sugars having a free aldehyde group in open chain form (solution)

• Monosaccharides can be oxidized by relatively mild oxidizing agents such as

cupric (Cu2) ion. The carbonyl carbon is oxidized to a carboxyl group.

• All Monosaccharides such as Glucose, fructose, glyceraldehyde, galactose

etc. and disaccharides lactose and maltose can reduce cupric ion and are
called reducing sugars.

• Cupric ion oxidizes glucose and certain other sugars to a complex mixture of
carboxylic acids. This is the basis of Fehling’s reaction.
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Ring structure- Haworth formula

• Cyclic structures of sugars are more accurately represented in Haworth

perspective formulas than in the Fischer projection commonly used for linear
sugar structures.

• In Haworth projections the six-membered ring is tilted to make its plane almost
perpendicular to that of the paper, with the bonds closest to the reader drawn
thicker than those farther away and numbering of the carbons is done in a
clockwise direction beginning with the anomeric carbon.

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Haworth projections

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Disaccharides
• Disaccharides (such as maltose, lactose, and sucrose) consist of two
monosaccharides joined covalently by an O-glycosidic bond, which is formed
when a hydroxyl group of one sugar molecule, typically cyclic, reacts with the
anomeric carbon of the other .

• Because maltose has a free OH group at C-1 of glucose, it is a reducing sugar.

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Disaccharides

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Polysaccharides

• Most carbohydrates found in nature occur as polysaccharides

• Polysaccharides, also called glycans, differ from each other in the identity of their
recurring monosaccharide units, in the length of their chains, in the types of
bonds linking the units, and in the degree of branching.

• Homopolysaccharides contain only a single monomeric species

• Heteropolysaccharides contain two or more different kinds

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 Amylopectin Glycogen
branches about every branches every
24-30 linear linkages 8-12 glucose units

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Heteropolysaccharides

• These heteropolysaccharides, the glycosaminoglycans, are a family of linear

polymers composed of repeating disaccharide units. They are unique to animals
and bacteria and are not found in plants.

• Hyaluronic acid forms clear, highly viscous solutions that serve as lubricants in
the synovial fluid of joints and give the vitreous humor of the vertebrate eye its
jellylike consistency (the Greek hyalos means “glass”.

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Heteropolysaccharides

• Hyaluronan is also a component of the extracellular matrix of cartilage and

tendons, to which it contributes tensile strength and elasticity.

• Hyaluronidase, an enzyme secreted by some pathogenic bacteria, can hydrolyze

the glycosidic linkages of hyaluronan, rendering tissues more susceptible to
bacterial invasion.
• Hyaluronidase is also present in high concentration in testes, seminal fluid, and
in certain snake and insect venoms.
• Hyaluronidase of semen is assigned an important role in fertilization as this
enzyme clears the gel (hyaluronic acid) around the ovum allowing a better
penetration of sperm into the ovum.

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Chondroitin Sulfate

• Chondroitin sulfate (Greek chondros, “cartilage”) contributes to the tensile

strength of cartilage, tendons, ligaments, and the walls of the aorta.

• Dermatan sulfate (Greek derma, “skin”) contributes to the pliability of skin and is
also present in blood vessels and heart valves.

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Agar

• Agar is a complex mixture of polysaccharides.

• The remarkable gel-forming property of agarose makes it useful in the

biochemistry laboratory.

• Agarose gels are used as inert supports for the electrophoretic separation of
nucleic acids, an essential part of the DNA-sequencing process.

• Agar is also used to form a surface for the growth of bacterial colonies.

• Another commercial use of agar is for the capsules in which some vitamins and
drugs are packaged.
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Biomedical Importance of Carbohydrates

• Chief source of energy.

• Constituents of compound lipids and conjugated proteins.

• Certain carbohydrate derivatives are used as drugs like cardiac

glycosides/antibiotics.

• Lactose principal sugar of milk—in lactating mammary gland.

• Degradation products utilized for synthesis of other substances such as fatty

acids, cholesterol, amino acid, etc.

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Biomedical Importance of Carbohydrates

• Constituents of mucopolysaccharides which form the ground substance of

mesenchymal tissues.

• Inherited deficiency of certain enzymes in metabolic pathways of different

carbohydrates can cause diseases, e.g. galactosemia, glycogen storage diseases
(GSDs), lactose intolerance, etc.

• Derangement of glucose metabolism is seen in diabetes mellitus.

• Seminal fluid is rich in fructose and sperms utilise fructose for energy. Fructose is
formed in the seminiferous tubular epithelial cells from glucose.

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Biomedical Importance of Carbohydrates

• Various food preparations, such as baby are produced by hydrolysis of grains and
contain large amounts of maltose.

• From nutritional point of view they are thus easily digestible.

• In lactating mammary gland, the lactose is synthesised from glucose by the duct
epithelium and lactose present in breast milk is a good source of energy for the
newborn baby.

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Biomedical Importance of Carbohydrates

• Glycosides are found in many drugs, spices and in the constituents of animal
tissues.

• Cardiac glycosides- digitalis

• Agar

• In human: Used as laxative in constipation. Like cellulose, it is not digested, hence

add bulk to the faces (“roughage” value) and helps in its propulsion.

• In microbiology: Agar is available in purified form. It dissolves in hot water and on

cooling it sets like gel. It is used in agar plate for culture of bacteria.

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