Mamalapat, Mohamidin K.

9/17/2023
Chem 2065 AY2023-24

Lipids and Proteins Are Associated in Biological Membranes

1. Differentiate among the different kinds of lipids according to their structural

components

Lipids can be divided into two main groups. First is the open-chain
compounds which means that they have a polar head group and long nonpolar
tails. This includes fatty acids, triacylglycerols, sphingolipids,
phosphoacylglycerols, and glycolipids. The second type is the fused-ring
compounds which includes steroids.

Lipids can also be classified into three main types, the triglycerides,
phospholipids, and sterols.

 Triglycerides is made up of glycerol and three fatty acids. Glycerol here is

the three-carbon backbone while the fatty acids are the long chains of
carbon molecules attached to the glycerol backbone.

 Phospholipids also have a glycerol backbone like the triglycerides

however, it only has two fatty acids attached to the glycerol backbone and
the third fatty acid is bonded to a phosphate group.

 Sterols are quite different from the first two. Most sterols do not have any
fatty acid but instead have multi-ring structures. This contains complex
molecules that has interlinking rings of carbon atoms, with attached
carbon, hydrogen, and oxygen side chains.
2. Characterize lipids based on fatty acids

Fatty acids are an important component of lipids. Its structure consists of a

carboxyl group at the polar end and hydrocarbon chain at the nonpolar tail. They
are considered amphipathic because the carboxyl group is hydrophilic while the
hydrocarbon tail is hydrophobic

3. Describe the characteristics of naturally occurring fatty acids (chain length, type
of unsaturation)

Naturally occurring fatty acids usually contain an even number of carbon atoms,
hydrocarbon chains generally unbranched, and may be classified accordingly
through the presence and number of C-C double bonds.

 Saturated fatty acids do not have C-C double bonds and only contain
single bonds.

 Unsaturated fatty acids have C-C double bonds in the chain. Usually,
naturally occurring unsaturated fatty acids have cis configuration. A cis
double bond puts a kink in the hydrocarbon tail, while the trans is like the
saturated fatty acid in its fully extended conformation.
4. Predict the effect of chain length on the mp of fatty acids

The principle of melting point is that as the molecular weight increases, the
melting point also increases. If we go back to organic chemistry, as the chain
gets longer there are relatively more electrons in the molecule which means that
there are stronger intermolecular forces between the molecules which require
more energy to break these forces thus melting points are higher. Therefore, the
longer the chain length the higher the melting point.

5. Predict the effect of unsaturation on the mp of fatty acids

Unsaturated fatty acids have lower melting points compared to saturated fatty
acids. Saturated fatty acids are denser since they have more hydrogen atoms
and do not contain any double bond. On the other hand, unsaturated fatty acids
have double bonds which result in “bends” in the molecule. The intermolecular
interactions are lesser thus lower melting point.

6. Describe the structure and function of triacylglycerols

Triacylglycerol is formed through the ester linkages of three fatty acids with a
glycerol. The three ester groups are the polar part while the tails of the fatty acids
are the nonpolar. They accumulate in the adipose tissue and provide means of
storing fatty acids, particularly in animals. In many organisms, extra
carbohydrates in the body are stored as triacylglyceride in the fat tissue.

7. Differentiate between fats and oils

Fats are mainly derived from animals, tend to be solid at room temperature,
mainly composed of saturated fatty acids thus no double bond in the molecular
structure, have higher melting point, stored in adipocytes, and two types are
trans and saturated fat. On the other hand, oils are usually derived from plants,
tend to be liquid at room temperature, composed of unsaturated fatty acids thus
lower melting point, stored in fat granules of plants, and two types are
monounsaturated and polyunsaturated fats.

8. Identify the role of lipases on triacylglycerols

Lipases is an enzyme used to hydrolyze ester linkages of triacylglycerol when an

organism uses fatty acids. It hydrolyzes triglycerides into their component fatty
acid and glycerol molecules. These molecules are taken up into the epithelial
 cells lining the intestinal wall, where they are resynthesized into triglycerides for
transport to muscles and adipose tissues. In the tissue, triglycerides are reformed
for storage until animals increase energy needs.

9. Recall the nature of saponification reactions based on your previous knowledge

in organic chemistry

Saponification is the reaction in which triglycerides react with sodium or

potassium hydroxide producing glycerol and fatty acid salt which is called “soap”.
Esters are cleaved back to carboxylic acid and alcohol with the reaction of water
and base.

10. Draw the structures of various phosphoacylglycerols (phosphatidic acid,

phosphatidyl esters)

11. Explain the amphipatic nature of phosphoacylglycerols based on their structures

Phosphoacylglycerols are amphipathic because they have long, nonpolar,

hydrophobic tails and polar highly hydrophilic head groups. The polar head group
is also charged because the phosphate group is ionized at neutral pH.

12. Describe the structure and function of waxes

 Waxes are made up of complex mixtures of an ester of long chain alcohol and
fatty acid (carboxylic acid). Waxes serve as protective coatings for both plants
and animals. In plants, it coats the stem, leaves, and fruit while in animals, waxes
are often found in fur, feathers, or the skin. Its hydrophobic nature allows them to
serve as water repellents on leaves, feathers, and cuticles of some insects. In
planktons, waxes serve as energy-storage substances.

13. Describe the structure and function of sphingolipids and sphingomyelin

● Sphingolipids, although do not contain glycerol, contain long-chain amino

alcohol sphingosine. It is composed of a sphingoid base backbone where a fatty
acid may be attached through an amide bond and a head group at the primary
hydroxyl. The head group can be a simple hydrogen to more complex species.
Sphingolipids can be found on both plants and animals and is very abundant in
the nervous system. It plays a significant role as a structural component of cell
membranes and as signaling molecules in the regulatory pathways.

● Sphingomyelins are phosphorus-containing sphingolipids. It contains a primary

alcohol group of sphingosines which is esterified into phosphoric acid, which is
also esterified into another amino alcohol called choline. Sphingomyelins are
structural components of cell membranes in the nervous system which contribute
to the stability of the membrane domains.

14. Describe the structure and function of glycolipids (ceramides and

cerebrosides)
 ● Glycolipids are carbohydrate-containing molecules and are components of
cellular membrane composed of a hydrophobic tail, and one or more hydrophilic
sugar groups. When a carbohydrate is bound to an alcohol group of a lipid
through glycosidic linkage, it forms glycolipids.

Ceramides are the parent compounds for glycolipids, and the glycosidic bond is
formed between the primary alcohol group of the ceramide and a sugar residue.
The resulting compound is called the cerebroside. Glycolipids are essential
parts of cell membranes and play a role in determining the blood group of an
individual and in tissue and organ specificity. They also act as receptors at the
surface of the red blood cells. The cerebrosides are found in nerve and brain
cells.

15. Describe the structure and function of glycolipids

When a carbohydrate is bound to an alcohol group of a lipid through glycosidic

linkage, it forms glycolipids. Glycolipids are essential parts of cell membranes
and play a role in determining the blood group of an individual and in tissue and
organ specificity. They also act as receptors at the surface of the red blood cells.

16. Describe the structure and function of steroids, especially cholesterol,

testosterone, estradiol

Steroids are one of the major classes of lipids, however, are totally different from
the structure of the other classes of lipids. Steroids’ main feature is the fused-ring
system which consists of three six-membered rings (A, B, C rings) and one five-
membered ring (D ring).

Cholesterol is the best known and the most abundant steroid in the body. The
single hydroxyl group in its structure is the only hydrophilic group. As a result, the
whole molecule of cholesterol is highly hydrophobic. Cholesterol is formed in the
brain and nerve tissues, and also the bloodstream. In membranes, it can modify
the role of membrane-bound proteins. It is also a precursor of other steroids and
of Vitamin D3. However, cholesterol is best known for its harmful health effects
where it is excessive in the blood. This may lead to atherosclerosis.
 Sex hormones are also steroids. Testosterone, the male hormone, is responsible
for the development of secondary sex characteristics. Progesterone and
Estrogen (Estradiol), the two female sex hormones, control the ovulation cycle.

17. Describe the important role of biological membranes

The molecular basis of a membrane’s structure lies in its lipid and protein
components. Biological membranes serve three primary functions: (1) separate
cells from external environment thus they keep toxic substances away from the
cell; (2) play important role in transport of substances in and out of the cell
because they contain receptors and channels that allow these specific molecules
that mediate cellular and extracellular activities to pass between organelles; (3)
biological membranes separate vital but incompatible metabolic processes
conducted within organelles. In addition, there are also a number of important
enzymes that can be found in membranes and depend on this environment for
their function.

18. Illustrate how amphipatic molecules like phosphoglycerides and glycolipids

form biological membranes

Phosphoglycerides are amphipathic molecules and are the principal components

of membranes. Phospholipids derived from glycerol are phosphogylcerides. They
are key components of cell membranes due to their amphipathic characteristics.
In aqueous solutions, these phospholipids are driven by hydrophobic interactions
which results in the fatty acid tails accumulating which minimizes interactions
with water molecules. The result of this is often the phospholipid bilayer.

19. Discuss how chain length of the fatty acid components of phosphoglycerides
affects membrane fluidity

Fatty acid tails of phospholipids affect membrane fluidity, since fatty acids can
vary in length and number of double bonds in the hydrocarbon chain. Longer
fatty acids are more rigid because the intermolecular interactions between the
phospholipid’s tail adds rigidity to the membrane. As a result, longer phospholipid
tails then more possible interactions between the tail and thus this reduces
membrane fluidity and permeability
20. Discuss how the degree of unsaturation of the fatty acid components of
phosphoglycerides affects membrane fluidity

The fluidity of the bilayer depends on its composition. In saturated fatty acids, the
hydrocarbon chain’s linear arrangement leads to the close packing of molecules
and thus rigidity. On the other hand, unsaturated fatty acids which have kinks,
which cause the disorder in the packing of the chains, which will make way to a
more open structure causing greater fluidity in the bilayer.

21. Discuss how heat affects membrane fluidity

Ordered bilayers become less ordered with application of heat. When bilayers
are comparatively disordered, they become even more disordered. This transition
takes place at a distinguishing temperature. Higher transition temperature is
needed for more rigid and ordered membranes compared to relatively fluid and
disordered membranes

22. Discuss how the presence of cholesterol affects membrane fluidity

Presence of cholesterol also enhances order and rigidity. The structure of

cholesterol, the fused-ring, is itself quite rigid and with the presence of
cholesterol, it stabilizes the long straight-chain arrangement of saturated fatty
acids through the Van der Waals interactions. At high temperatures, it stabilizes
the membrane and raises the melting point while at low temperature, it inserts
between phospholipids and prevents clustering together.

23. Explain how the natural lipid bilayer asymmetry affects possible membrane
composition (bulkier molecules are found in the outer layer)

The bilayer’s inner and outer layers are composed of mixtures of lipids; however,
their compositions differ and are used to distinguish the inner and other layers
from each other. The concentration of bulkier molecules is higher in the outer
layer while smaller molecules tend to be in the inner layer in which they are more
tightly packed.

24. Characterize the properties of proteins found in biological membranes according

to their location (peripheral proteins. integral proteins, lipid-
anchored proteins)

Integral proteins are embedded in the whole bilayer whereas peripheral proteins are
located on the inner or outer surface of the phospholipid bilayer. Unlike integral
membrane proteins, peripheral membrane proteins do not stick into the hydrophobic
core of the membrane, and they tend to be more loosely attached. Lipid-anchored
proteins are proteins located on the surface of the cell membrane that are covalently
attached to lipids embedded within the cell membrane.
25. Describe the fluid-mosaic model of biological membranes

The fluid-mosaic model is the membrane model where proteins and a lipid bilayer
exist side by side without covalent bonds between the proteins and lipids. It
describes the membrane as a tapestry of several types of molecules
(phospholipids, cholesterols, and proteins) which are constantly moving. This
movement is what helps the membrane maintain a barrier between the inside
and outside of the cell environment.

26. List the three main functions of membranes and membrane proteins

The three main functions of membranes are transport, catalysis, and receptor
property.

o Transport – since membranes are semipermeable barriers to the flow of

substances in and out of the cell

o Catalysis – Enzymes can be bound to membranes and the enzymatic reactions

takes place on the membrane

o Receptor property – proteins bind specific biologically important substances

that trigger biochemical responses to the cell

27. Differentiate between passive transport and active transport

Passive transport is when a substance moves from a region of higher

concentration to one of lower concentration, or it is the movement of a substance
in the same direction as the concentration gradient thus the cell does not use
energy.

Active transport is when a substance moves from lower concentration region to

higher concentration across a concentration gradient thus requiring the cell to
expend energy.
28. Differentiate between simple diffusion and facilitated diffusion across the
biological membrane

Simple diffusion happens when a molecule moves directly through a membrane

without interacting with another molecule. This is seen in small and uncharged
molecules passing through membranes. The rate of movement is controlled by
the concentration difference across the membrane.

Facilitated diffusion is the process where the moving of molecules happens

passively through a membrane using a carrier protein where the molecules bind.
This is observed in larger molecules, especially the polar ones.

29. Use the mechanism of glucose permease to illustrate facilitated diffusion

The glucose concentration in the blood is higher than the intracellular glucose
concentration, creating a glucose gradient. Glucose passes through a carrier
protein called glucose permease. This is considered a facilitated diffusion
because no energy is expended and a protein carrier is used.

30. Explain how the rate of transport against a concentration gradient can be used to
elucidate a facilitated diffusion mechanism

It is identified that facilitated diffusion at the rate of transport, when plotted

against concentration of molecules being transported, creates a hyperbolic curve
like that of the Michaelis-Menten enzyme kinetics, and they display saturation
behavior.

31. Differentiate the structural difference between regular globular

proteins found in the cytoplasm and the intrinsic proteins found in the
membrane
 Globular proteins that are found in cytoplasm are larger compared to that of the
intrinsic proteins in membranes. Globular proteins are more compact and in
round shape. The primary structure of globular proteins is simply the sequence of
amino acids forming the peptide chain. The peptide chain is folded in an ordered
and repetitive manner and thus creates the secondary structures.

Intrinsic proteins penetrate and bind tightly with the lipid bilayer. They have
amino acids with nonpolar side chains at the interface between the protein and
the nonpolar central region of the lipid bilayer.

32. Differentiate between primary active transport and secondary active

transport

In primary active transport, movement of molecules against a gradient is directly

linked to the hydrolysis of a high energy molecule while in the secondary active
transport, transport of molecules across the membrane utilizes energy in other
forms than ATP. This energy comes from electrochemical gradients which is
created by pumping ions out of the cell.

33. Use the mechanism of the sodium-potassium pump as an example to

illustrate primary active transport

The sodium-potassium pump is moving potassium ions into a cell and

simultaneously moving sodium ions out of the cell. One subunit of the protein
hydrolyzes the ATP and transfers the phosphate group to an aspartate side chain
on another subunit. Binding of the three Na+ ions from the interior of the cell
takes place simultaneously. The phosphorylation of one subunit causes a
conformational change in the protein thus opening a channel or pore through
which the three Na+ ions can be released to the extracellular fluid. Outside the
cell, two phosphorylated K + ions bind to the pump enzyme. This second
 conformational change regenerates the original form of the enzyme and allows
the two K+ ions to enter the cell. The pumping process transports three Na+ ions
out of the cell for every two K+ ions transported into the cell.

34. Use the mechanism of the galactoside permease as an example to illustrate

secondary active transport

In bacterial cells, lactose concentration is higher inside compared to outside thus

moving lactose into the cell needs energy to take place. The galactoside
permease does not directly hydrolyze ATP. Instead, it uses the higher
concentration of H+ outside to drive the concentration inside the cell. As long as
more energy is available allowing the hydrogen ions to flow than it is required to
concentrate the lactose, the process is possible. However, to arrive with higher
concentration of H ions on the outside than inside, another primary active
transporter must establish an H ion gradient. Proton pumps are active
transporters that create H ion gradients.

35. Use the mechanism of the LDL receptor to illustrate the receptor properties of
cell membranes

LDL is the principal carrier of cholesterol in the bloodstream. It consists of various

lipids and a protein. The protein in the LDL binds to the LDL receptor of the cell
 and complex form is pinched off into the cell through endocytosis. Then, the
receptor protein is recycled back to the cell surface. Oversupply of cholesterol
causes problems and inhibits the synthesis of LDL receptors. Few receptors
mean the level of cholesterol in the bloodstream increases.

36. Provide an overview of the conversion of beta-carotene into vitamin A (retinol)

When an organism requires Vitamin A, the beta-carotene is converted in the

liver. Two molecules of Vitamin A are formed from one molecule of the beta-
carotene. One way to convert beta-carotene to vitamin A is to break it apart at
the center. The breakdown occurs in the walls of the small intestine and is
catalyzed by beta-carotene dioxygenase to from the retinal.

37. Explain the important role of vitamin A in the primary chemical reaction of
vision

Opsin is the derivative of Vitamin A that plays a crucial role in vision when it is
bound to protein. The cone cells in the retina of the eye contain several types of
opsins and is responsible for the vision in bright light and colored vision. The rod
cells contain only one type of opsin which is responsible for dim light vision.

38. Explain the important role of vitamin D in the regulation of calcium and
phosphorus

Vitamin D plays a major role in the regulation of calcium and phosphorus

metabolism. The presence of Vitamin D3 leads to increased synthesis of Ca2+ -
binding protein, which increases the absorption of dietary calcium in the
intestines. This process results in calcium uptake by the bones. Deficiency can
lead to rickets, condition of the bones of growing children.

39. Provide an overview of the conversion of cholesterol into vitamin D

Vitamin D3 is formed from cholesterol by UV radiation from the sun and is

processed in the body to form hydroxylated derivatives. Cholesterol is
photochemically cleaved, and the photochemical cleavage occurs and the
electron arrangements after the cleavage form the Vitamin D3.

40. Explain why vitamin D does not fit the definition of 'vitamin'
 Vitamin is any of a group of organic compounds which are essential for normal
growth and nutrition and are required in small amountin the diet because they
cannot be synthesized by the body. Vitamin D is a steroid hormone produced
from cholesterol when the skin is exposed to the sun thus it is not a vitamin
because it is produced in the body.

41. Explain how vitamin E plays a role as an antioxidant

Vitamin E is an established antioxidant which is found to be a good reducing

agent thus it reacts with oxidizing agents before they can attack other
biomolecules. The vitamin’s antioxidant action protects important compounds
from degradation. Vitamin E is to react with, and thus remove, the very reactive
and highly dangerous substances called free radicals which plays a part in
development of cancer and aging process.

42. Explain the important role of vitamin K in blood clotting

Vitamin K is required in the process of blood clotting. It modifies prothrombin and

other proteins involved in the process. In prothrombin, addition of another
carboxyl group alters the side chains of several glutamate residues of
prothrombin. This produces y-carboxyglutamate residues. Two carboxyl groups
in proximity form bidentate ligand which bind calcium ions. If prothrombin is not
modified in this way, it does not bind Ca2+ that is required in blood clotting.

43. Provide an overview on the structure and functions

of prostaglandins, leukotrienes, and thromboxanes (the eicosanoids)

● Prostaglandins, leukotrienes, and thromboxane are derived from fatty acids.

Prostaglandins are produced in the prostate gland, it contains a five-membered ring, it
controls blood pressure, stimulation of smooth-muscle contraction and induction of
inflammation. It also inhibits aggregation of platelets
Leukotrienes are found in leukocytes and have three conjugated double bonds, it
constricts smooth muscles and inflammatory properties and may be involved in
rheumatoid arthritis
Thromboxanes are third class derivatives of arachidonic acid; contain cyclic ethers;
known to induce platelet aggregation and smooth-muscle contraction