Department of Botany

Mid Term Assignment

Course Code: CHEM-5104 Course Name: Biochemistry

Due Date:25/04/2020 Submission Date:25/04/2020
Course teacher: Rana Mahmood Anwar Student Name: Zeenat Falak Sher
Student ID: BBOF18E021 Session: 2018-2022
Program: BS-Botany Semester: 4th
Regular/Self-support: Self- Support Main Campus/ Ex- PPP: University of Sargodha

ASSIGNMENT COVER SHEET

Title of the assignment: Lipids
Word count: 2449
Marks awarded by teacher:
Lipids:

Lipids are naturally occurring (organic) compounds that are insoluble in polar solvents such
as water . Their insolubility can be attributed solely to their long hydrophobic hydrocarbon
chains. These hydrophobic chains may be saturated or unsaturated. Unsaturated chains
contain double or triple covalent bonds between adjacent carbons while saturated chains
consist of all single bonds. Lipids are composed of a glycerol molecule bonded to long
hydrocarbon chain(s) (can be single or multiple) and, depending on the lipid, to other
molecules—such as a phosphate group (phospholipids).
Some examples of the types of lipids are: neutral, saturated, (poly/mono) unsaturated fats and
oils (monoglycerides, diglycerides, triglycerides), phospholipids, sterols (steroid alcohols),
zoosterols (cholesterol), waxes, and fat-soluble vitamins (vitamins A, D, E, and K). Lipids
have many different biological functions such as fuel molecules, structural building blocks
for phospholipids and glycolipids, covalent attachments to guide molecules to specific
membrane locations, and intracellular messengers.

"Chemical structure of the saccharolipid lipid A as found in E. Coli."

There are three common types of Membrane Lipids. They are phospholipids, glycolipids, and
cholesterol. [Structural Biochemistry].

Fats:
Consists of glycerol and 3 fatty acids. Fats are created via 3 condensation reactions creating
ester linkages that link the fatty acid carboxyl groups to the hydroxyl groups in glycerol.
There are two different types of fatty acids, saturated and unsaturated. In a saturated fatty
acid, it has the maximum number of hydrogen atoms possible, thus there are no double
bonds. There are only single bonds. Since saturated fatty acids are only single bonds, it can
pack more tightly together at room temperature and this makes it a solid at room temperature.
An example of a saturated fatty acid is butter. An unsaturated fatty acid has one more double
bond. These double bonds create a kink in the hydrocarbon tail, which in return results in
looser packing. At room temperature, it is a liquid. An example of this is oil.
Phospholipids:
They are found in biological membranes. The components of phospholipids include a
hydrophobic tail and hydrophilic head. The hydrophobic tail consists of two hydrocarbon
chains. The hydrophilic head consists of choline, phosphate, and glycerol. The fatty acids
give a hydrophobic barrier, whereas the remainder of the molecule has hydrophilic properties.
Phospholipids spontaneously form lipid bilayers due to amphipathic nature of lipid
molecules. Phospholipids are found in all cell membranes.

Cholesterol:
Cholesterol is a steroid and they are built from 4 fused hydrocarbon rings. The hydrocarbon
tail is connected to the steroid at one end, and a hydroxyl group is connected to the other end.
Cholesterol is a steroid important in cell membranes and acts as a precursor to some sex
hormones. However, prokaryotes do not have cholesterol.
Triglycerides:

Neutral fats (triglycerides) are composed of fatty acid hydrocarbon chains bonded to a single
glycerol molecule. Fatty acids consist of long hydrocarbon chains with a carboxyl group
while glycerol consists of 3 carbons and 3 hydroxyl groups. Fatty acids are the building
blocks of fat molecules. The method by which the three fatty acid chains in a triglyceride
attach to a single glycerol molecule is called dehydration synthesis. Dehydration synthesis is
also used in various other reactions, including the joining of two monosaccharides to form a
disaccharide. Triglycerides function primarily in energy storage, as a form of insulation, and
to protect and cushion cells and organs.

There is an image of a triglyceride molecule with three neutral fatty acid chains and a
glycerol group

Saturated fatty acids contain single bonds between the carbons of the hydrophobic chain.
Saturated fatty acids originate from animals and are found as component chains in a
triglyceride molecule. Saturated fatty acids exist in the solid state at room temperature.
Unsaturated fatty acids however contain one (monounsaturated) or more (polyunsaturated)
double bond(s) between the carbons of the hydrocarbon chain, which causes the molecule to
bend. Triglycerides with too many bends cannot be packed as closely together as neutral fatty
acids and therefore are less dense. Below is an example of a saturated fatty acid

Triglycerides composed of many fatty acids that melt at lower temperatures than those
triglycerides with saturated fatty acids. These unsaturated fatty acids do not bind at their
maximum number of hydrogen’s because of double bonding between the carbons of the
chain. Unsaturated fatty acids originate from plants and are found as component chains to
triglyceride molecules. Unsaturated fatty acids exist in the liquid state at room temperature.

(E)-4-oxohexadec-2-enoic acid, An Unsaturated Fatty Acid

These images depict a saturated fatty acid chain (contain single carbon bonds) and an
unsaturated fatty acid chain (contain double carbon bonds).

Phospholipids:

Phospholipids are modified triglycerides with one of the fatty acid chains replaced with a
phosphate group. They are made by four distinguished groups: fatty acid chains, a platform, a
phosphate group, and an alcohol attached to the phosphate. The fatty acid chains are
hydrocarbon chains that are typically 14-24 carbons in length. The platform is either glycerol
or sphingosine, which is an amino alcohol with a hydrocarbon chain. Phospholipids have a
very characteristic non-polar fatty acid chain portion and a polar phosphate portion. The
amphipathic character of phospholipids contribute in its' crucial role in phospholipid bilayers.
The polar phosphate group is capable of interacting with water molecules and spontaneously
forms a bilayer in an aquatic environment. Phospholipids orientate themselves so that the
polar heads are facing the water molecules and the hydrophobic fatty acids are oriented
toward the inside of the bi-layer. The bi-layer environment enables the non-polar fatty acid
chains to stay together, avoiding the water while the hydrophilic phosphate group is oriented
toward the water. Phospholipids participate in the formation of the cell membrane by the
coming together of two layers of phospholipids. The phospholipids are responsible for the
membrane's semi-permeability and fluidity.

The structure describe a phospholipid:

This image illustrates the components and orientation of the hydrophilic phosphate group and
the hydrophobic fatty acid chains that form the lipid bi-layer.

Phospholipid is the most common group of lipids. In fact, cell membranes as well as
organized cellular compartments are all made up of these phospholipids. They can form
structures called micelles, in which when phospholipids congregate, the hydrophobic fatty
acid tails join together in the centre of the sphere away from the aqueous environment and the
polar heads are exposed to the outside. Structures such as liposomes can also be artificially
formed from these lipids: using high frequency sound waves to sonicate the sample
containing phospholipids and molecules of interest to create phospholipid vesicles that
contain the molecules of interest. This is often used to deliver drugs to the cells and study
how drugs pass through the membrane.

The plasma membrane is made up of the phospholipid bilayer. The membrane is an

amphipathic sheet-like structure that is fluid and electrically polarized. The membrane itself
has little functions, but the proteins that are integrally and peripherally integrated to the
membrane help mediate many of the functions that we contribute to membrane. The
membrane is asymmetric in that the proteins are randomly distributed across the membrane,
some are attached inside the cell, some outside, and others integrated within membrane. Also,
rapid lateral diffusion and slow transverse diffusion contribute both to the membrane's
asymmetric characteristic and fluidity. In transverse diffusion, phospholipids are flipped
inside-out or outside-in, and this flipping is regulated by filasse. However, the longer the fatty
acid chains are, the less likely for transverse diffusion to occur. Longer chains also decreases
the fluidity of the plasma membrane. There are other factors that may affect plasma
membrane's fluidity. For example, the better arranged the fatty acids chains are, the less fluid
the membrane is. On top of that, the more unsaturated the fatty acids are, the more fluid the
membrane is. This is because the double bonds bend the chains that allows sloppy
arrangements. The interruption of cholesterol within the membrane also causes more fluidity
since the polar hydroxy group in cholesterol disrupts the hydrophobic environment within the
phospholipid bilayer.

Glycolipids:

Glycolipids are sugar(glyco-)containing lipids. They are derived from sphingosine instead of
a form of phospholipids that derives from glycerol (phospholipids exist in both derivatives
from glycerol and sphingomyelin platform). Another difference from phospholipids is that
glycolipids contain a sugar unit (can be glucose or galactose) instead of a phosphate group.

Examples: Glycolipid molecules exist from the most basic molecule, cerebroside which
contains 1 fatty acid unit, a sphingosine backbone, and 1 sugar unit (glucose or galactose), to
the most complex molecules containing branched chains of multiple sugar residues (up to
seven residues in gangliosides).

Properties: When glycolipids exist in membranes, their sugar residue terminal always face the
extracellular side.

Chemical structure of Glycolipids

Cholesterol:
Cholesterol is a form of lipids that differs from the rest of its relatives. It is relatively medium
molecule that contains 4 adjacent cyclic hydrocarbon molecules with three six-member rings
and one five-member ring that has a hydroxyl and a saturated hydrocarbon chain terminals.
The molecule functions as a bufferor a temperature stabilizer for the membrane in which it
can make up of 25% of the membrane. When exist in membranes, the 4 cyclic molecules in
the cholesterol molecule lay parallel to the fatty acid chains of the phospholipids, meanwhile
the hydroxyl terminal points in the direction with the polar phospholipid heads in which it
interact with.

Cholesterol molecules exist primarily in nerve cells. The molecule binds to the myelin sheath
membrane which provides an outer coating that protects the nerve cell from its surroundings.

It is an essential predecessor to sex hormones that exists in males (testosterone) and females
(oestradiol). Also an essential component in vitamin D that enables the body to utilize
calcium to form bones.

Animals acquire very little cholesterol from the food they eat; they make cholesterol within
the body. Although cholesterol is essential for many processes and structural function, it can
be detrimental to have excess cholesterol. Too much cholesterol in the blood will cause
blockages in the arteries which can result in heart disease, high blood pressure, and stroke.
Only 0.25% of human beings retain High Cholesterol disease from heredity, however people
are gaining high cholesterol in their blood from the food they eat (especially people in
America).
Membrane Properties:

The cell membrane has a set of properties that are contributed to the presences of the lipids as
well as proteins. 1. Structures are like sheets. 2. They are formed by lipids, proteins, and
carbohydrates. 3. The membrane is amphipathic (contain hydrophobic and hydrophilic
regions). 4. Each protein allows for the function of the membrane. 5. Membranes are held on
by weak, non-covalent bonds. 6. The structure is asymmetric. 7. It is high in fluidity. 8. The
membrane is polarized.
Fluidity:

The presence of the lipids in the membrane structure of a cell is vital for the cell especially
affecting its fluidity. As addressed in the section below, this is necessary to allow things to
flow in and out of the cell. One factor that plays a big role in this is cholesterol as shown
below. Another one is the presence of double bonds. The more the double bonds, the greater
the amount of kinks or curve in the lipid and therefore more free space. The length of the
lipids also plays a role. Lipids move in two distinct ways. Most commonly they interact in
lateral diffusion where they switch places with the lipid to the left or right of them. Other
times, they go through transverse diffusion where they flip flop with the ones whose tails they
are facing. This is due to the weak, Van der Waals interaction of the lipid molecules. The
longer the lipid is, the stronger this interaction is, therefore decreasing the mobility of the
lipids. Decrease lipid mobility yields in decreasing the fluidity of the membrane.

Cholesterol and fluidity:

This shows the cholesterol molecules submerged in the lipid bilayer

Cholesterol is an important factor in membrane permeability, that is, how much can flow
through the cell. Cholesterol acts as a 'buffer' to prevent against any extremes. Obviously, the
membranes permeability cannot be too fluid as to allow anything inside the cell (harmful
agents), but at the same time, the membranes permeability must be fluid enough as to let
out/let in important agents that need to enter the cell.

Cholesterol is a hydrocarbon steroid with one single alcohol group, which leads to its
amphiphatic nature.

Generally,

1.AT LOW TEMPERATURES: Cholesterol in a membrane leads to a more fluid

membrane.
2.AT HIGH TEMPERATURES: Cholesterol in a membrane leads to a less fluid
membrane.
Ether Lipids with Branched Chains:
Two major factor that separates Archaea (bacteria) from Bacteria is the Archea's cell
membranes phospholipid consists of ether linkages and the fatty acid hydrocarbon chains are
completely saturated and branched with a methyl group every 5 carbons. These simple
structural differences provide Archeabacteria drastic difference from bacteria in terms of their
habitat's harsh environments. These 2 factors contribute to the chemical properties that their
membrane is more resistant to hydrolysis (ether versus ester linkages) and resistant to
oxidation (branched saturated hydrocarbon chains).

Phospholipids and Glycolipids Readily Form Bimolecular Sheets in Aqueous

Media:

Phospholipids and glycolipids have amphipathic characteristics which enables them to form a
micelle or a "lipid bilayer". Due to the hydrophobic hydrocarbon tail and the hydrophilic
polar head group, the lipids arrange in a form where the polar groups face water while the tail
is away from water. One formation is the micelle where the lipids arrange themselves in a
circle with the head groups making the circumference while the tails are inside. A more
favourable formation is the lipid bilayer or the bimolecular sheet. This arrangement has the
lipids form a barrier where the polar head groups face the aqueous media and the
hydrophobic tail face inside away from water. This type of formation is favourable to cell
membranes for it forms a barrier from the extracellular fluid and protects the cytoplasm
within the cell. Integral and peripheral proteins may be present in the lipid bilayer to allow
certain functions to occur such as transportation of ions or acting as pumps.

References:
Berg, Jeremy; Tymoczko, John; Stryer, Lubert. Biochemistry, 6th edition. W.H. Freeman and
Company. 2007. Berg, Jeremy M., Tymoczko, John, L., Stryer, Lubert. Biochemistry.
Seventh Edition.

The Organics of Biochemistry:

"Lipid bilayer." Wikipedia. 7 December 2012. 7 December 2012

Viadiu, Hector. "Lipids and Cell Membranes." UCSD, 19 November 2012.