KPJ HEALTHCARE UNIVERSITY

COLLEGE

BPH 1063 PHARMACEUTICAL

ORGANIC CHEMISTRY I

ASSIGNMENT 1 (CBL)

ChM. AFIQ BIN AZIL

NAME : SITI AMIRAH HAKIMAH BINTI MOHD FAIRUZ

NO. MATRIKS : 2062191008

BACHELOR OF PHARMACY (HONS)
PROGRAM :
COHORT 7
 The World Diabetes Day is celebrated on the 14 th on November each year.
There is a lot of chemistry revolved around diabetes.

Norman (n.d.) stated that, diabetes mellitus is a disorder characterized by

hyperglycemia or elevated blood glucose which is blood sugar in our body. Our
bodies function best at a certain level of sugar in the bloodstream. Diabetes is the
name of the condition where the blood sugar level consistently runs too
high. Diabetes is the most common endocrine disorder and has potential long-term
complications that can affect the kidneys, eyes, heart, blood vessels, and nerves.
Diabetes mellitus divided into two major subgroups which is Type 1
diabetes and Type 2 diabetes. This division is based upon whether the blood
sugar(glucose) problem is caused by insulin deficiency (type 1) or insulin resistance
(type 2). Insulin deficiency means there is not enough insulin being made by the
pancreas due to a malfunction of their insulin producing cells. In this form of 
diabetes, specialized cells in the pancreas called beta cells stop producing insulin
. Insulin resistance occurs when there is plenty of insulin made by the, but the cells
of the body are resistant to its action which results in the blood sugar being too high. 
Both glucose and insulin are organic compounds because in chemistry, organic
compounds are generally any chemical compounds that contain carbon-hydrogen
bonds. These are the structure of glucose (Figure 1.0) and insulin (Figure 2.0).

Figure 1.0 : Structure of Glucose

Figure 2.0 : Structure of Insulin
 Carbohydrates may be defined as
polyhydroxy aldehyde or ketone.
Carbohydrates are designated as D-
or L- according to the
stereochemistry of the highest
numbered chiral carbon of the Fisher
Projection (Z.,2014).

Figure 1.1 : Structure of Glucose in Straight-chain

Form (Fisher Projection) and Cyclic Form

Chatterjee (2013) stated that 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 on the
D-configuration. This is the reason why glucose is also known as D-glucose as its
hydroxy group of the highest numbered chiral carbon is pointing to the right (Figure
1.1). Glucose is by far the most common carbohydrate and classified as a
monosaccharide, an aldose, a hexose, and it is a reducing sugar. It is also known as
dextrose, because it is dextrorotatory (meaning that as an optical isomer is rotates
plane polarized light to the right) and also an origin for the D-designation . Glucose is
also called blood sugar as it circulates in the blood at a concentration of 65-110
mg/dL of blood (Katta,2014).

Monosaccharides are simple sugars, or the compound which possess a free

aldehyde (CHO) or ketone (C=O) group and two or more hydroxyl (OH) groups, They
are the simplest sugars and cannot be hydrolyzed further into smaller units. Glucose
contains aldehyde, alcohol, and hemiacetal groups and it exists in a straight-chain
form and in various cyclic forms (Figure 1.1). Refer to Figure 1.1, in the straight-form
(Fisher projection), the functional group at C-1 is an aldehyde group. The functional
groups on C-2 to C-6 are alcohol groups. In the cyclic form, the functional group on
C-1 is a hemiacetal group. A hemiacetal has an OH and an OR group on the same
carbon atom (Pvino, 2010).

Following is the properties of D-glucose (monosaccharides) (Ibrahim,2013):

1. Mutarotation :
 When a monosaccharide is dissolved in water, the optical rotatory power of
the solution gradually changes until it reaches a constant value. For ex :
When D-glucose is dissolved in water, a specific rotation of +112.2 ° is
obtained, but this slowly changes , so that at 24h the value has become
+52.7°. This gradual change in specific rotation is known as mutarotation. This
phenomenon is shown by number of pentoses, hexoses and reducing
disaccharides.
2. Glucoside formation :

When D-glucose solution is treated with methanol and HCl, two compounds
are formed, these are α – and β-D- glucosides. Thus, formed glucosides are
not reducing sugar and also does not show phenomenon of mutarotation.

3. Reducing power :

Sugars having free or potentially free aldehyde or ketone group have an

ability to reduce the cupric copper to cuprous. The following reaction is
followed by equation below:

Reducing sugar + 2 Cu²⁺ oxidized + 2 Cu⁺

(cupric) (sugar) (cuprous)

4. Oxidation and Reduction reaction:

The alcoholic OH, aldehyde (COH) or ketone (C=O) group are oxidized to
carboxyl group with certain oxidizing agents. The oxidation may be brought
under mild or with vigorous oxidizing condition. In reduction, the aldehyde
group present in D-glucose give hexahydric alcohol. The aldehyde reduction
product of glucose is the molecule sorbitol. The reduction of the five-
carbon sugar xylose produces another sugar alcohol, xylitol.

Joshi, Parikh, and Das (2007) found that

insulin is a protein chain or a
polypeptide hormone that consist of 51
amino acids in an insulin molecule that
produced by beta cells (ß-cells) in the
islets of Langerhans in the pancreas
which is a gland located behind
stomach. It allows your body to use
glucose for energy. Based on Figure
2.0, insulin composed of 2 polypeptide
chains A (with 21 amino acid residues)
and B (with 30 amino acid residues. Both
A chain and B chain are linked together
by two inter-chain
disulfide bridges. In addition, A chain Figure 2.1 : Amino Acid Structure
contains an intra-chain disulfide bridge
linking residue 6 and 1 (p. 20).

Figure 2.1 shows the amino acid structure in an insulin molecule. Insulin is primarily
made up of carbon, hydrogen, nitrogen and oxygen atom. The molecular formula of
human insulin is C257H383N65O77S6 and has a molecular weight of 5734 gram per mol.
Amino acids serve primarily as the building blocks for the proteins and the order of
the amino acids determines function and shape of protein. Proteins are simply a long
chain of amino acids, without water due to peptide bonding (Pvino,2010). Boyd
(2006) stated that the conversion of proinsulin to insulin in human is by proteolytic
cleavage. Proteolytic cleavage is basically the process of breaking the peptide bonds
between amino acids in proteins. This process is carried out by enzymes called
peptidases, proteases or proteolytic cleavage enzymes.

Insulin is a hormone that moves glucose from your blood into the cells for energy
and storage. Insulin is a chemical messenger that allows cells to absorb glucose, a
sugar, from the blood. Clusters of cells in the pancreas called islets produce the
hormone and determine the amount based on blood glucose levels in the body. The
higher the level of glucose, the more insulin goes into production to balance sugar
levels in the blood. A delicate balance of insulin regulates blood sugar and many
processes in the body. If insulin levels are too low or high, excessively high or low
blood sugar can start to cause symptoms. If a state of low or high blood sugar
continues, serious health problems might start to develop such as diabetes (Felman
& Prelipcean, 2018).

According to National Institutes of Health (2020), causes for each type of diabetes
mellitus is differ from each other as type 1 diabetes is generally considered to be an
autoimmune disorder. Autoimmune disorders occur when the immune system
attacks the body's own tissues and organs.  People with type 1 diabetes, their
immune system damages the insulin-producing beta cells (ß-cells) in the pancreas
causes the inability to produce sufficient insulin which results in low rates of glucose
uptake into muscle and adipose tissue. Without the presence of insulin, many of the
body’s cells cannot take glucose from the blood and therefore the body uses other
sources of energy. Ketones are produced by the liver as an alternative source of
energy, however, high levels of the ketones can lead to a dangerous condition
called ketoacidosis. People with type 1 diabetes will need to inject insulin to
compensate for their body’s lack of insulin.
In type 2 diabetes, your body has become resistant to the effects of insulin. This
means your body needs more insulin to get the same effects. Therefore, your body
overproduces insulin to keep blood glucose levels normal. However, after many
years of overproduction, the insulin-producing cells in your pancreas burn out. Type
2 diabetes affects people of any age, but typically develops later in life. Depending
on their level of insulin resistance, people with type 2 diabetes  may also need to
take insulin injections to manage their blood sugar levels (Editor,2020).

Ala (2014) stated that the concentration of glucose in blood and urine can be
determined by Fehling's test. Fehling's test can be used to distinguish aldehyde and
ketone functional groups. The Fehling's solution is added to the sample to be tested
and the mixture is heated. Aldehydes are oxidized, giving a positive result (red
colour), but ketones do not react (blue colour), unless they are alpha-hydroxy-
ketones. Fehling’s solution cannot be used for aromatic aldehyde. Fehling's solution
contains copper(II) ions complexed with tartrate ions in sodium hydroxide solution.
Complexing the copper(II) ions with tartrate ions prevents precipitation of copper(II)
hydroxide.

Based on Figure 3.1, formation of red precipitate in Fehling’s reaction shows the
presence of a reducing sugar such as glucose. The reactive species of the
reaction is Copper (II) Oxide (Cu2 O). This is reduced to red Cuprous Oxide that
would be responsible for the brick red precipitate.

Figure 3.1 : Result of Fehling’s Test

The basic equation is followed below:

The aldehydic group of the glucose molecule is oxidized to carboxylic group.
That is D-glucose is converted to D-gluconic acid (refer Figure 3.2).

Figure 3.2 : Fehling’s Test Equation for Glucose

Fehling's test can be used as a common test for monosaccharides (due to the
oxidizable aldehyde group) and other reducing sugars (e.g. maltose, glucose and
fructose). In the area of clinical chemistry, Fehling's test is widely used for detecting
diabetes mellitus to screen for glucose in urine and blood. Excess of glucose in
blood and urine can lead to diabetes.

In addition, a variation on Fehling’s test called Benedict’s test was used in the first
kits to detect urine glucose. The blue color of the copper ions meant that there was a
range of yellows and oranges available depending upon the amount of the sugar
(and so of the red copper oxide). Benedict's solution contains copper(II) ions
complexed with citrate ions in sodium carbonate solution. The copper(II) ions
prevents the formation of a precipitate, this time is the formation of copper(II)
carbonate.

Fehling’s test is not used for the analysis of carbohydrates in clinical samples
because Fehling’s solution is always prepared fresh in the laboratory. It is made
initially as two separate solutions, known as Fehling's A and Fehling's B. Fehling's A
is a blue aqueous solution of copper (II) sulphate pentahydrate crystals, while
Fehling's B is a clear solution of aqueous potassium sodium tartrate (also known as
Rochelle salt) and a strong alkali (commonly sodium hydroxide). There are many
advantages of Benedict’s test over Fehling’s test such as :

Fehling’s Test Benedict’s Test

The reagent is unstable
It has to be freshly prepared in two parts
which has to be stored separately.
It is only qualitative test.
The strong alkali (potassium hydroxide)
present in the reagent can destroy base
the destruction of carbohydrate.
Auto reduction of cupric hydroxide occur
in resulting false positive test.
It is more sensitive.
The reagent is very stable.
Single solution is prepared and storage
is convenient.
It is both qualitative and semi-
quantitative test.
Since sodium carbonate is a very weak
base, the destruction of carbohydrate is
insignificant.
Auto reduction doesn’t take place.
It is less sensitive.

Nowadays, better and more specific tests were developed for glucose and the non-
specific copper tests became a thing of the past. For example, the glucometer.
Glucose oxidase is an enzyme that is highly specific for glucose and forms the basis
of very sensitive tests. The enzyme oxidizes glucose using oxygen which is
converted to hydrogen peroxide (while the glucose gets converted to a cyclic ester
that hydrolyses to glucuronic acid). The hydrogen peroxide can be used to generate
a color change and this can be seen by eye, for example on a plastic urine test strip,
or by spectrophotometer. Glucose oxidase is reasonably stable and can be isolated
from the bread mold Aspergillus niger. It is important that blood glucose is kept within
the normal range in diabetics and test strips, as well as more accurate assays with
the same underlying chemistry, helps the patient and their doctor to achieve this
(Figure 3.3)

Figure 3.3 : Equation of Glucose Oxidation Reacts with a Dye (Mishra,2012)

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