LIPIDS I-IV

Prepared By: Group 6

III. Lipid Classes based upon whether or not
saponification occurs when a lipid is placed in
CHAPTER 1 basic aqueous solution.
(Saponification, it is the chemical reaction in which
the building blocks of fats and oils (triglycerides)
CONTENTS OF LIPIDS CHAPTER 1
Note:
I. Definition of lipids.
II. Lipids classes based on their biochemical A “cis” fatty acid – hydrogens are on the same side
functions. of the fatty acid backbone.
III. Lipid classes (Saponification).
IV. Major Lipid Classes and definition. A “trans” fatty acid – hydrogens are on the opposite
V. Physical Properties of fatty acids & Lipids. side of the fatty acid backbone.
VI. Number of double bonds.
VII. Fatty Acid chain length & Fatty acid react with lye to form soap. Saponification literally
Nomenclature.
means "turning into soap" from the root
VIII. The Essential fatty acids: Linoleic and Linolenic
word, sapo, which is Latin for soap. The products of
acid.
IX. Guidelines for saturated fatty acid consumption. the saponification reaction are glycerin and soap.
X. Storage of excess energy. Chemically, soap is a fatty acid salt.)
1. SAPONIFIABLE LIPIDS
converted into smaller molecules
when hydrolysis occurs
I. What are lipids? (triacylglycerols, phospholipids,
sphingoglycolipids, and biological
- Organic substances that are relatively insoluble in waxes).
water and soluble in organic solvents (e.g. ether, 2. NON SAPONIFIABLE LIPIDS
chloroform and benzene) cannot be broken up into smaller units
since they do not react with water
• Lipids are non-polar (hydrophobic) (cholesterol, steroid hormones, bile
compounds. acids, and eicosanoids).
• Lipids are all insoluble in polar solvents like
water but highly soluble in the non-polar or IV. MAJOR LIPID CLASSES
weakly polar organic solvents.
1) Fatty acids 3) Triglycerides
• Most membrane lipids are having a non-polar
2) Glycerophospholipids 4) Sphingolipids
end and a polar end.
1. FATTY ACIDS - Molecules that are long
II. LIPIDS CLASSES BASED ON THEIR
chains of lipid-carboxylic acid found in fats
BIOCHEMICAL FUNCTIONS
and oils and in cell membranes as a
component of phospholipids and glycolipids.
Energy- storage lipids Triacylglycerols (Carboxylic acid is an organic acid containing
the functional group -COOH.)
Membrane Lipids Phospholipids, Classification of fatty acids according to
sphingoglycolipids, and number and position of double bonds;
cholesterol Saturated (single C-C bond)
Unsaturated (Double band)
o Monounsaturated (1 double band)
o Polyunsaturated (2 or more double
Emulsification Lipids Bile acids
bands)

Messenger Lipids Steroid hormones and V. PHYSICAL PROPERTIES OF FATTY

eicosanoids ACIDS AND LIPIDS;
1) Water Solubility
2) Melting points
Protective-coating Biological waxes - Influenced by both carbon chain
lipids length and degree of unsaturation.
- Melting point of saturated fatty
acids is greater than the melting.

Chapter 1 Prepared By: Joseph Hilario

 point of unsaturated fatty acids with - Inflammation
the same number of carbon atoms. - Food sources: Nuts and seeds

VI. NUMBER OF DOUBLE BONDS Linolenic acid → ω-3 eicosanoids

- dilation of blood vessels
Influences; -Physical Nature of fatty acid
• Double bonds in fatty acids usually have the Saturated Fatty Solid at room
“cis” configuration. Most naturally occurring acids temperature
fatty acids have an even number of carbon
atoms. Monounsaturated Thick liquids or soft
• There is free rotation about C-C bonds in the fatty acids solids
fatty acid hydrocarbon, except where there is a
double bond. Each cis double bond causes a
Polyunsaturated Liquid
kink in the chain. Rotation about other C-C fatty acids
bonds would permit a more linear structure than
shown, but there would be a kink.
VII. FATTY ACID CHAIN LENGTH - Food Sources: Oils (soybean,
Affects; safflower, corn, flaxseeds)
- Chemical Properties
- Physiological functions IX. GUIDELINES FOR SATURATED FATTY
- Solubility in water ACIDS CONSUMPTION

• Saturated Fatty Acid intake positively related to

VII. FATTY ACID NOMENCLATURE
risks for cardiovascular disease.
(Nomenclature, a collection of rules for naming • Dietary Guidelines: Saturated Fatty acids
things, is important in science and in many other should constitute no more than 10% of total
situations). kilocalories
o Alpha (α) Nomenclature - based on positions
2. TRIGLYCERIDES
and types of double bonds relative to the
are a type of fat (lipid) found in your blood.
carboxylic end of the fatty acids
When you eat, your body converts any
o Omega (ω) Nomenclature - Fatty acids
calories it doesn't need to use right away
categorized into groups based on where the
into triglycerides. The triglycerides are
first double bond is located relative to the
stored in your fat cells. Later, hormones
methyl (ω) end.
release triglycerides for energy between
o Examples:
meals. If you regularly eat more calories than
- Omega-3-fatty acid - first double bond
you burn, particularly from high-carbohydrate
is between the 3rd and 4th carbons
foods, you may have high triglycerides
from the ω end
(hypertriglyceridemia).
- Omega-6-fatty acid - first double bond
is between 6th and 7th carbons from
FUNCTIONS:
the ω end.
VIII. THE ESSENTIAL FATTY ACIDS: LINOLEIC 1) Provide essential fatty acids for body
AND LINOLENIC ACIDS functions
• Not produced in the body 2) Energy production
• Linoleic acid: makes arachidonic acid 3) Insulation
• Linolenic acid: converted to 4) Protection
docosahexaenoic acid (DHA) and
eicosatetraenoic acid (EPA)
X. STORAGE OF EXCESS ENERGY

• Large number of triglycerides can be

FUNCTIONS:
stored in small space
Eicosanoids • Energy yield from lipids relatively
- lipid mediators of inflammation; high (9kcal/g)
made from arachidonic acid and • Body has infinite ability to store
EPA excess energy in adipose tissue.
- includes:
prostaglandin thromboxane
prostacyclin leukotrienes
- assist and regulate immune and
cardiovascular systems act as
chemical messengers.
Linoleic acid → ω-6 eicosanoids

Chapter 1 Prepared By: Joseph Hilario

 CHAPTER 2
Compounds made up of isoprene units.

CONTENTS OF LIPIDS CHAPTER 2 • VITAMIN K – essential for blood clotting

process. Necessary for the carboxylation of
glutamic acid (Glu) residues in certain
I. Terpenes
proteins.
II. Cholesterol
• VITAMIN E – antioxidant (protects
III. Steroids derived from cholesterol
membrane lipids from oxidative damage)
IV. Eicosanoids
• VITAMIN D – precursor to a hormone that
V. Prostaglandins regulates calcium metabolism.
VI. Inhibition of Cyclooxygenase
• VITAMIN A – furnishes the visual pigment of
VII. Thromboxane the vertebrate eye and is a regulator of
VIII. Leukotrienes gene expression during epithelial cell
growth.

II. CHOLESTEROL

• Most common steroid in animals

• Precursor for all other animal steroids
• Component of animal cell plasma
membranes
• Component of lipoprotein complexes in the
blood
• Constituent of plaques that form on arterial
walls in atherosclerosis
• Also, a precursor of vitamin D, cardiac
glycosides, Sitosterol of the plant kingdom, and
some alkaloids.

Cholesterol is a 27 carbon compound with a

unique structure with a hydrocarbon tail, a central
sterol nucleus made of four hydrocarbon rings,
and a hydroxyl group. The center sterol nucleus
or ring is a feature of all steroid hormones. The
hydrocarbon tail and the central ring are non-
polar and therefore does not mix with water.
Therefore cholesterol (lipid) is packaged together
with apoproteins (protein) in order to be carried
through the blood circulation as a lipoprotein.

I. TERPENES

• Are a class of lipids formed from

combinations of two or more molecules of 2-
methyl-1,3-butadiene (isoprene)
• Largest single class of compounds found in
essential oils, also called isoprenoids – are
made up of isoprene molecules.
• Each isoprene molecule (sometimes called
isoprene unit) contains five carbon atoms
with double bonds.
• Terpene hydrocarbons are classified
according to the number of isoprene units:
Monoterpenes: 2 isoprene units, 10 carbon atoms.

o Sesquiterpenes: 3 isoprene units, 15

carbon atoms.
o Diterpenes: 4 isoprene units, 20
carbon atoms.
o Triterpenes: 6 isoprene units, 30
carbon atoms.
o Tetraterpenes: 8 isoprene units, 40
carbon atoms.

Chapter 2 Prepared By: Juliana Cruzada

III. STEROIDS DERIVED FROM CHOLESTEROL
• Testosterone (androgen) and estradiol
(estrogen) – mediate the development of sexual
characteristics and sexual function in animals.
o Testosterone – the male sex hormone, is
produced in the testes.
o Estradiol – one of the female sex
hormones, is produced in the
ovaries and placenta.
• Progesterone – controls menstrual cycle
and pregnancy
• Glucocorticoid (cortisol) – participate in the
control of carbohydrate, protein and lipid
metabolism.
• Bile acids (cholic and deoxycholic acid) –
detergent molecules; secreted in bile from
the gallbladder; assist in the absorption of
dietary lipids in the intestine.
• Cortisol and aldosterone – hormones
synthesized in the cortex of the adrenal
gland; they regulate glucose metabolism
and salt excretion.
• Prednisolone and prednisone – are
synthetic steroids used as anti-inflammatory
agents.
IV. EICOSSANOIDS
Involved in:
• Reproductive function
Chapter 2
• Inflammation, fever, and pain associated
with injury or disease
• Formation of blood clots and the regulation
of blood pressure
• Gastric acid secretion
V. PROSTAGLANDINS
• Contains a five-carbon ring originating from
the chain of arachidonic acid.
• Name is derived from the prostate gland,
the tissue from which they were first isolated by
Bengt Samuelsson and Sune Bergstrom.
• Two groups of prostaglandins:
o PGE, for ether- soluble
o PGF, for phosphate buffer- soluble
Each group contains numerous subtypes,
named PGE1, PGE2, and so forth.
• Act in many tissues by regulating the
synthesis of the intracellular messenger 3,5-
cyclic AMP (cAMP).
• Some prostaglandins stimulate contraction
of the smooth muscle of the uterus during
menstruation and labor.
• Prostaglandins in a third group elevate body
temperature (producing fever) and cause
inflammation and pain.
• PGE – increases FA levels by increasing
cAMP synthesis; mediates inflammation.
• PGE2 – causes dilation of blood vessels;
activates cellular immune cells and attracts
macrophages towards the site of injury.
• Macrophages – with enzymes that destroy
tissue structure (site of injury) entry of water
inflammation
VI. INHIBITION OF CYCLOOXYGENASE
• Nonsteroidal anti-inflammatory drugs
(NSAIDs) – aspirin, ibuprofen, and
meclofenamate inhibit the enzyme
prostaglandin H2 synthase (also called
cyclooxygenase or COX), which catalyzes an
early step in the pathway from arachidonate to
prostaglandins and thromboxane.
VII. THROMBOXANES
• Have a six- membered ring containing
ether.
• Produced by platelets (also called
thrombocytes)
• Causes platelet coagulation (formation of
blood clots)
VIII. LEUKOTRIENES
• First found in leukocytes.
• Potent muscle contractant (induces
contraction of the muscle lining the airways to
the lung)
• Overproduction of leukotriene causes asthmatic
attacks, and leukotriene synthesis is one target
of anti- asthmatic drugs such as prednisone.
Prepared By: Juliana Cruzada
 CHAPTER 3
Phosphatidylinositol with inositol as polar head
group is one glycerophospholipid.
CONTENTS OF LIPIDS CHAPTER 3

I. Membrane of Lipids
Phosphatidylinositol is an acidic phospholipid that
II. Phospholipids
contains an inositol attached to the phosphate
III. Glycerophospholipids
group of phosphatidic acid and is found especially
IV. Phosphatidate
in cell membranes where it is precursor to several
V. Sphingolipids
substances that mediate cellular activity as second
VI. Cerebroside
messengers the parent phospholipid.
VII. Cholesterol
VIII. Lipoproteins

I. Membrane of Lipids
group of compounds (structurally similar to
fats and oils) which form the double-layered
surface of all cells (lipid bilayer).

II. Phospholipids

→ Major components of cell membranes

→ Aid in digestion, absorption, transport of
lipids, cellular metabolism
→ Amphipathic (contains both polar and non-
polar portion)
→ Made up of two fatty acids, a phosphate
group, and a glycerol molecule.

III. Glycerophospholipids (phosphoglycrides)

→ Common constituent of cellular membranes.

→ They have a glycerol backbone
→ most abundant phospholipids
→ found in highest amounts in the membranes
of all cells
→ present in very small quantities in fat stores.
IV. Phosphatidate
→ fatty acids are esterified to hydroxyls
→ common intermediate in the synthesis of
phospholipids and triacylglycerols
Phosphatidylcholine with choline as polar head
group, is another glycerophospholipid.
Phosphatidylcholine is a chemical contained in eggs,
soybeans, mustard, sunflower, and other foods. It is
found naturally in the body in all cells.
Phosphatidylcholine is also a source of choline in the
body. Phosphatidylcholine is used for ulcerative
colitis. There is some scientific research that supports
this use.

Chapter 3 Prepared By: Edrian Diaz

V. Sphingolipids
→ are derivatives of the lipid sphingosine,
which has a long hydrocarbon tail, and a
polar domain that includes an amino group.
→ Other derivatives of sphingosine are
commonly found as constituents of
biological membranes.
→ The amino group of sphingosines can form
an amide bond with a fatty acid carboxyl, to
yield a ceramide.
Sphingomyelin
→ has a phosphocholine or
phosphoethanolamine head group.
→ common constituent of plasma membranes
VI. Cerebroside
→ is a sphingolipid (ceramide) with a
monosaccharide such as glucose or galactose as
polar head group.
→ Ganglioside is a ceramide with a polar
head group that is a complex oligosaccharide,
including the acidic sugar derivative sialic acid.
→ Cerebrosides and gangliosides,
collectively called glycosphingolipids,
commonly found in the outer leaflet of the plasma
membrane bilayer, with their sugar chains
extending out from the cell surface.
Chapter 3
VII. Cholesterol
→ important constituent of cell membranes has
a rigid ring system and a short-branched
hydrocarbon tail.
→ largely hydrophobic.
→ has one polar group, a hydroxyl, making it
amphipathic.
VIII. Lipoproteins
→ combined lipid (cholesterol) with proteins
and phospholipids are soluble in water because
the surface consists of polar lipids.
→ It carries cholesterol from the liver to various
tissues are called low-density lipoproteins or
LDLs or the “bad cholesterol” because it
contributes to increased blood cholesterol levels.
→ Those that carry excess cholesterol from
tissues back to the liver are called high-density
lipoproteins or HDLs or “good cholesterol”
because it contributes to lessening blood
cholesterol levels.
Prepared By: Edrian Diaz
 CHAPTER 4

- All of the lipid molecules in cell membranes

CONTENTS OF LIPIDS CHAPTER 4 are amphipathic (or amphiphilic)—that is, they have
a hydrophilic (“water-loving”) or polar end and
I. Biological Membranes a hydrophobic (“water-fearing”) or nonpolar end.
II. Amphipathic Lipids
III. Amphipathic Detergents
IV. Membrane Fluidity
V. Integral Proteins
Possible molecular arrangements depending on
VI. Flip-Flop of Lipids
VII. Fluid Mosaic Model the lipid:
VIII. Passive Diffusion o Various Micelle Structures
IX. Facilitated Diffusion - Example: Spherical Micelle (stable configuration
X. Active Transport for amphipathic lipids with a conical shape such as
XI. Ouabain and Digitoxigenin fatty acids)
XII. Emulsification of Lipids: Bile o Bilayer
- most stable configuration for amphipathic lipids
with a cylindrical shape
I. BIOLOGICAL MEMBRANES - Example: Phospholipids

Cytoplasmic Membrane (Cell Membrane)

- It is a fluid phospholipid layer embedded with
proteins and glycoproteins.
- The phospholipid bilayer is arranged so that the
polar ends of the molecule form the outermost and
innermost surface of the membrane while the non-
polar ends form the center of the membrane.

Figure 2. Structure of a Bilayer and Spherical Micelle

The membrane lipid molecules are amphipathic.
The most numerous are the phospholipids.
When placed in water they assemble
spontaneously into bilayers, which form sealed
compartments that reseal if torn.

Figure 1. Diagram of a Cytoplasmic Membrane

Functions of the Cytoplasmic Membrane:

o Separate the cytoplasm from the surroundings
o Exclusion of certain toxic ions and molecules
from the cell Figure 3. Amphipathic Lipid Aggregation that Form
o Accumulation of nutrients in Water
o Energy transduction III. Amphipathic Detergents
o Cell locomotion
o Reproduction - These are molecules that can be used to extract,
o Signal transduction process solubilize, and manipulate (disrupt or form)
o Interactions with molecules or other cells in the membrane proteins from biological membranes for
subsequent biochemical and physical
vicinity
characterization.
o Hydrophobic domains of detergents substitute
II. Amphipathic Lipids
for lipids, coating hydrophobic surfaces of
- When associated with water, these form integral proteins
complexes in which polar regions are in contact with o Polar domains of detergents interact with water
water and hydrophobic regions away from water.

Chapter 4 Prepared By: Jelica Luna

- Due to their unique structure, detergents can act as
excellent solubilizing agents. They have a polar,
hydrophilic (water-loving) head group which extends
from a long hydrophobic (water-fearing) tail.
Figure 4. Detergent Solubilization
- If detergents are removed, purified integral proteins
tend to aggregate & come out of solution. Their
hydrophobic surfaces associate to minimize contact
with water.
Figure 5. Motion of a Single Phospholipid in a Bilayer
IV. Membrane Fluidity
- The interior of a lipid bilayer is normally highly fluid
- Cell membranes are composed of phospholipids,
proteins, and carbohydrates loosely attached to one
another through chemical interactions.
- Molecules are generally able to move about in the
plane of the membrane, giving the membrane its
flexible nature called fluidity.
o In the liquid crystal state, hydrocarbon chains of
phospholipids are disordered and in constant
motion.
o At lower temperature, a membrane containing a
single phospholipid type undergoes transition to
a crystalline state in which fatty acid tails are fully
extended, packing is highly ordered, & van der
Waals interactions between adjacent chains are
maximal.
o Kinks in fatty acid chains, due to cis double
bonds, interfere with packing in the crystalline
state, and lower the phase transition
temperature.
Chapter 4
Figure 6. Structure of a Liquid Crystal and Crystal
V. Integral Proteins
- These have domains that extend into the
hydrocarbon core of the membrane. Often they span
the bilayer.
- Integral membrane proteins are permanently
embedded within the plasma membrane.
- Intramembrane domains have largely hydrophobic
surfaces that interact with membrane lipids.
Functions of Integral Proteins:
o Channeling or transporting molecules across the
membrane
o Act as cell receptors
Figure 7. Membrane Proteins
Integral membrane proteins can be classified
according to their relationship with the
bilayer:
o Transmembrane proteins span the entire
plasma membrane. Transmembrane
proteins are found in all types of biological
membranes.
o Integral monotopic proteins are permanently
attached to the membrane from only one side.
Figure 8. Lateral Mobility
Prepared By: Jelica Luna
o High speed tracking of individual lipid
molecules has shown that lateral movements
are constrained within small membrane
domains.
o Hopping from one domain to another occurs
less frequently than rapid movements within a
domain.
o The apparent constraints on lateral
movements of lipids (and proteins) have been
attributed to integral membrane proteins,
anchored to the cytoskeleton, functioning as a
picket fence.

VI. Flip-flop of Lipids

Figure 10. Fluid Mosaic Model
- Transverse diffusion or flip-flop involves the
movement of a lipid or protein from one membrane TRANSPORT PROCESSES
surface to the other. Unlike lateral diffusion,
transverse diffusion is a fairly slow process due to
the fact that a relatively significant amount of energy
is required for flip-flopping to occur.

Figure 11. General Classes of Transport Systems

VIII. Passive Diffusion

- Passive diffusion is the process by which

molecules diffuse from a region of higher
Figure 9. Flip-flop of Lipids concentration to a region of lower concentration. It is
the most important mechanism for passage of drugs
through membranes.
- Flip-flop would require the polar head-group of a
lipid to traverse the hydrophobic core of the
membrane.
- The two leaflets of a bilayer membrane tend to
differ in their lipid composition.
- Flippases catalyze flip-flop in membranes where
lipid synthesis occurs.
- Some membranes contain enzymes that actively
transport particular lipids from one monolayer to the
other.
Figure 12. Movement of Solutes across a
VII. Fluid Mosaic Model Semipermeable Membrane

- The fluid mosaic model of the plasma membrane
describes the plasma membrane as a fluid
combination of phospholipids, cholesterol, and
proteins. Carbohydrates attached to lipids
(glycolipids) and to proteins (glycoproteins) extend
from the outward-facing surface of the membrane.
- The transported species moves across the
membrane in the thermodynamically favored
direction without the help of any specific transport
system/molecule
IX. Facilitated Diffusion

Chapter 4 Prepared By: Jelica Luna

- Facilitated diffusion is similar to passive
diffusion with the exception that carrier
proteins embedded in the membrane
bilayer facilitate the transfer of chemicals across the
membrane.
- It is a type of transport facilitated by a transporter.
(Examples: protein pores, carrier molecules as well
as membrane vesicles)

Two features of proteins:

o They facilitate net movement of solutes only in
the thermodynamically favored direction; display
a measurable affinity and specificity for the
transported solute
o Display saturation behavior Figure 14. Ouabain Action

X. Active Transport XII. Emulsification of Lipids: Bile

- Active transport is defined as movement of a Emulsifier

solute from a region of low electrochemical - It is a substance that can scatter and steady
potential on one side of the cell membrane to a water-insoluble substances as colloidal particles
region of higher electrochemical potential on the in an aqueous solution.
opposite side.
- It is driven in an energetic sense (the most
common energy input is ATP hydrolysis).
- Example: Monovalent cation transport: Na + K+
ATPase (known as sodium pump)

Figure 15. Fat Emulsification

Figure 13. Two Types of Active Transport
XI. Ouabain and Digitoxigenin
- Active ingredients of digitalis (foxglobe leaf
extract)
- Digitalis has been used to treat congestive
heart failure; strengthens muscle contractions
without increasing the heart rate and thus
increases the efficiency of the heart.
- Digitalis inhibits the efflux of Na ions, raising the
intracellular [Na] enough to activate a Na-Ca2
antiporter in cardiac muscle; elevated cytosolic
[Ca2], strengthens the contractions of the heart.
Bile Acids
- These are cholesterol derivatives that functions
as a lipid-emulsifying agent in the aqueous
environment of the digestive tract.
Bile
- It is a fluid, synthesized in the liver from
cholesterol, stored in the gallbladder, and
secreted into the small intestine during digestion.
Bile also comprises bile pigments (breakdown
products of hemoglobin, cholesterol itself, and
electrolytes such as bicarbonate ion. The bile
acids that are present increase the solubility of
the cholesterol in the bile fluid.

Chapter 4 Prepared By: Jelica Luna

References: o https://www.sciencedirect.com/topics/chemistry/
passive-
Chapter 1:
diffusion#:~:text=Passive%20diffusion%20is%2
Chapter 26: Lipids. (n.d.). Retrieved from University of 0the%20process,penetrate%20lipid%20membr
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http://www.chem.ucalgary.ca/courses/351/Car o https://www.sciencedirect.com/topics/chemistry/
ey5th/Ch26/ch26- facilitated-diffusion
0.html#:~:text=Lipids%20are%20all%20insolubl
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Chemical Nomenclature. (n.d.). Retrieved from Lumen

Learning:
https://courses.lumenlearning.com/chemistryfo
rmajors/chapter/chemical-nomenclature/

FIsher, D. (2020, January 12). Saponification in Soap

Making. Retrieved from The Spruce Crafts:
https://www.thesprucecrafts.com/saponificatio
n-in-soap-making-517092

Triglycerides: Why do they matter? (2020, September

29). Retrieved from Mayo Clinic:
https://www.mayoclinic.org/diseases-
conditions/high-blood-cholesterol/in-
depth/triglycerides/art-20048186

William C. Shiel Jr., M. F. (n.d.). Medical definition of

fatty acids. Retrieved from Medicine Net:
https://www.medicinenet.com/script/main/art.
asp?articlekey=15387

Chapter 3:
https://www.webmd.com/vitamins/ai/ingredient
mono-
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search%20that%20supports%20this%20use.
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#:~:text=All%20of%20the%20lipid%20molecule
s,and%20two%20hydrophobic%20hydrocarbon
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study-of-membrane-proteins
o https://www.jove.com/science-
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o https://bio.libretexts.org/Bookshelves/Introducto
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