Biochemistry-1 Carbohydrate-I

CARBOHYDRATE-I

Intended Learning Outcomes (ILOs):

By the end of this lecture students will be able to:

▪ Identify the Biological importance of Carbohydrates

▪ Describe structure and classes of carbohydrates
▪ List general and chemical characteristics of monosaccharides
▪ Explain what is meant by asymmetric carbon and isomerism
▪ Compare between types of isomerism
▪ Recognize common monosaccharides and their biological
importance
▪ Communicate with his colleagues during lecture to solve
problems

BY:
Dr. Tamer AlShafie
Assoc. Professor of Medical Biochemistry

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Biochemistry-1 Carbohydrate-I

CARBOHYDRATES
Carbohydrates, termed as sugars, are ‘staff of life’ for most organisms.

Carbohydrates are also known as ‘saccharides’ (from Greek word

sakcharon = sugar or sweetness) since many of those of relatively small
molecular weight have a sweet taste.

1. Importance/Functions of Carbohydrates
A. Carbohydrates provide energy for:
Brain Function
Heart Pumping
Muscle Exercise

B. Carbohydrates serve as food reserve material. For example,

glycogen in muscle tissue.

C. Carbohydrates are components of several animal and plant

tissues. In animals, carbohydrates are components of skin,
connective tissue, tendons, cartilage and bone. In plants, cellulose
is a component of wood and fiber.

D. Carbohydrates are components of cell membrane. For example,

glycoproteins and glycolipids.

E. Derivative of carbohydrates can form vitamins. For example,

Vitamin C (Ascorbic acid).

F. Derivative of carbohydrates can be used as drugs. For example,

antibiotics; Streptomycin is a glycoside and Erythromycin is an
amino-sugars derivative.

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Biochemistry-1 Carbohydrate-I

2. General Structure of Carbohydrates

Carbohydrates are organic compounds composed of carbon, oxygen
& hydrogen. The H : O ratio as in water 2: 1 with the general formula:
Cn (H2O)n , hence they are named "hydrates of carbon".
They are broadly defined as: derivatives of polyhydroxy aldehydes or
polyhydroxy ketones to cover a wide variety of compounds.
However, it was found some EXCEPTIONS such as:
❖ Some carbohydrates do not have the required ratio of hydrogen
to oxygen (e.g., Deoxyribose, C5H10O4).
❖ Some carbohydrates do not coincide with the above general
formula because they contain nitrogen, phosphorus and sulfur
(e.g., glucosamine, C6H13O5N)
❖ Some non-carbohydrates have C, H and O and the ratio of H : O is
also the same as in water, but are not a carbohydrates (e.g.
formaldehyde, CH2O and acetic acid C2H4O2)
3. Classification of Carbohydrates: carbohydrates are usually classified
into 3 groups:
✓ Monosaccharides
✓ Oligosaccharides
✓ Polysaccharides

A. Monosaccharides
(Mono=one; sakcharon=sugar) – (-ose is the suffex)
A. General Characteristics:
− Monosaccharides are the simplest sugars which cannot be
hydrolyzed into smaller units.
− Their general formula is: Cn (H2O)n or CnH2nOn
− They can be present in a linear molecule (Fischer structure) or
cyclic (ring) molecule (Haworth structure).

Linear molecule Ring molecule

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Biochemistry-1 Carbohydrate-I

B. Nomenclature and Classification:

1. According to Number of carbon atoms, monosaccharides can be
divided into: trioses, tetroses, pentoses, hexoses etc.,
The carbon atoms of a monosaccharide are numbered from the end
beside the aldehyde or ketone group.

Hexose (Glucose)
2. According to Type Specific group, monosaccharides can be divided
into: Aldoses contain aldehyde group (—CHO) or Ketoses contain
ketone group (—C=O).

Aldose (Glucose) Ketose (Fructose)

3. According to both Number of carbon atoms and Type of Specific

group.
For example: Glycerose (= glyceraldehyde) is an aldotriose
Ribulose is a ketopentose
Glucose is an aldohexose.

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Biochemistry-1 Carbohydrate-I

C. Asymmetric Carbon & Isomerism:

 Asymmetric Carbon Atoms in Carbohydrates:
Asymmetric carbon is the carbon atom attached to which 4 different
atoms or groups.
All monosaccharides contain asymmetric carbon except
dihydroxyacetone (ketotriose).

 Isomerism:
The presence of asymmetric carbon atoms in monosaccharides
makes it possible to form isomers.
Isomers are compounds have same molecular formula but differ in
chemical structure and physical properties due to different molecular
arrangement. Number of possible isomers of a given compound depends
on number of asymmetric carbon atoms in its molecule.
No. of isomers = 2n (where n= no. of asymmetric carbons).
Types of Isomers:
1. Enantiomers (Mirror image) also called: Optical isomerism
Enantiomers are isomers that are mirror image to each other.

*Optical Activity: Due to the presences of asymmetric carbon atoms,

when a beam of plane-polarized light is passed through a solution of the
optical isomerism, it will rotate either to the:

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Biochemistry-1 Carbohydrate-I

Right (called: dextrorotatory, D-) OR Left (called: levorotatory, L-).

Most monosaccharides in mammals are in the D- form.
Glyceraldehyde is the reference for optical isomers since it has one
asymmetric carbon atom.
*Racemic Mixture:
Racemic mixture is a mixture of equal amounts of 2 different optical
isomers (D- form & L-form). It doesn't give any optical activity.
2. Diastomers (Not mirror image)
 Epimers (Linear form)
Epimers are isomers that differ in only ONE asymmetric carbon.

D-glucose and D-mannose are epimers with respect to C 2

 Anomers (Ring form)

Anomeric carbon: it is the carbon atom that present in the ring
form of the sugar and represents the sugar carbonyl carbon
(either —CHO or —C=O)
Anomers are isomers that differ in the anomeric carbon of the
sugar the ring form (in solutions).
Anomers are designated as: either α- or β- anomers.

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*Mutarotation:
If a freshly prepared sugar is left in water for few hours, it exhibits a
specific rotation change due to the change in α- & β- anomers ratios.

Examples:
I. 1CHO Contain aldehyde gr. Aldose
2CHOH No. of C. atoms = 4 Tetrose
3CHOH No. of Asymmetric C. = 2
4CH2OH Aldotetrose No. of Isomers = 4
CHO CHO CHO CHO
H-C-OH OH-C-H OH-C-H H-C-OH
H-C-OH OH-C-H H-C-OH OH-C-H
H-C-H H-C-H H-C-H H-C-H
OH OH OH OH
D-Erythrose L-Erythrose D-Threose L-Threose

II. 1CH2OH Contain ketone gr. Ketose

2C=O No. of C. atoms = 4 Tetrose
3CHOH No. of Asymmetric C. = 1
4CH2OH Ketotetrose No. of Isomers = 2
OH OH
H-C-H H-C-H
C=O C=O
H-C-OH OH-C-H
H-C-H H-C-H
OH OH
D-Erythrulose L-Erythrulose

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Biochemistry-1 Carbohydrate-I

D. Chemical Properties of Monosaccharides

Monosaccharides contain active groups responsible for their
chemical behavior; hydroxyl (OH) and aldehyde (CHO) or ketone (C=O).
 Reducing Properties:
All monosaccharides are reducing sugars because they always have
a free (-CHO) or (-C=O) group which undergo chemical reactions include:
− Reducing sugars can reduce chromogenic agents (e.g., Benedict’s
reagent or Fehling’s solution) and a specific color appears, with the
aldehyde group of the acyclic sugar becoming oxidized.

− Reducing sugars can undergo a 3-step reaction with phenylhydrazine

to form Osazone.

− Reducing sugars react with hydroxylamine to yield Oximes.

 Formation of Glycosidic bonds:

All monosaccharides contain hydroxyl groups (-OH) by which they can
make glycosidic bonds with other carbohydrates and non-carbohydrates
compounds. (Discussed Next Lecture)

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Biochemistry-1 Carbohydrate-I

E. Common Monosaccharides / Derivatives

 MONOSACCHARIDES:
1. Hexoses (glucose, fructose, galactose and mannose)
2. Pentoses and Deoxy sugars
1. Hexoses
#D-Glucose (grape sugar)
Sources:
Fruit juices, hydrolysis of starch, cane or beet sugar.
It can be obtained by hydrolysis of starch, cane sugar, maltose and
lactose.
Importance:
It is the most important carbohydrate in biology.
It is the blood sugar which the cell uses as the main source of energy
and metabolic intermediate.
#D-Fructose (fruit sugar)
Sources:
Fruit juices, honey, hydrolysis of cane or beet sugar.
It can be obtained by enzymic isomerization of glucose syrups for food
manufacture.
Importance:
It is an important component in the seminal fluid in man.
#D-galactose
Sources: Hydrolysis of lactose
Importance:
Synthesis of lactose in milk in the mammary gland.
It is a constituent of galactolipids, glycoprotein and glycosaminoglycans.
#D-Mannose
Sources: Hydrolysis of plant mannan gums
Importance: Constituent of glycoproteins
2. Pentoses
#D-ribose & Deoxy-ribose:
Sources: muscle and liver
Importance: D-ribose is a structural element of ribonucleic acid (RNA)
and coenzymes (e.g., ATP, GTP, NAD and NADP). Deoxyribose is a
structural element of nucleic acid (DNA)

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Biochemistry-1 Carbohydrate-I

 MONOSACCHARIDE DERIVATIVES:
1. Sugar alcohols
2. Sugar-phosphate esters
3. Amino sugars

1. Sugar alcohols (Alditols)

Sugar alcohols are obtained from reduction of aldehyde or keto
groups of sugar produces polyhydroxy alcohols or polyols. They are
characteristically sweet tasting, and widely used to sweeten sugarless
gum and mints. Examples….
Sorbitol:
It is used as sweetener and laxative.
It is built-up in eyes of diabetics is implicated in cataract formation.

Xylitol:
It is as sweet as sucrose and has been used as a food additive as well as a
sugar substitute for diabetics.
Ingestion of large amounts of xylitol causes bladder tumors as well as
oxalate stones in experimental animal models.

Inositol:
Myo-inositol is an important isomer of inositol.
It is a structural component of phospholipids and cell membrane.
It has an important role in cell signaling.

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2. Sugar-phosphate esters
Phosphate esters of hexoses are important metabolic intermediates.
Phosphate esters of ribose moiety are component of nucleotides
such as ATP and GTP.

3. Amino sugars
Amino sugars are sugars that contain an amino group (instead of a
hydroxyl group) at C-2 position.
Examples include β-D-glucosamine and β-D-galactosamine which are
found in many oligo- and polysaccharides.
Several antibiotics (e.g., erythromycin) contain amino sugars, which
are important for their antibiotic effect.

End of Lecture
Thank You...

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