08LipAMO Suarez
08LipAMO Suarez
08LipAMO Suarez
They are classified according to their chemical nature which fall into two main
categories. One group, which consists of open-chain compounds with polar head
groups and long nonpolar tails. This includes fatty acids, triacylglycerols,
sphingolipids, phosphoacylglycerols, and glycolipids. The second major group
consists of fused-ring compounds, the steroids; an important representative of
this group is cholesterol.
A fatty acid has a carboxyl group at the polar end and a hydrocarbon chain at the
nonpolar tail. These compounds are amphipathic because the carboxyl group is
hydrophilic but the hydrocarbon tail is hydrophobic. The carboxyl group is
ionizable.
A fatty acid in a living system normally contains an even number of carbon atoms
while the hydrocarbon chain is usually unbranched. A fatty acid is unsaturated if
there are carbon-carbon double bonds, if there are only single bonds, then it is
saturated. In unsaturated fatty acids, the stereochemistry at the double bond is
usually cis rather than trans. The difference between cis and trans fatty acids is
very important to their overall shape. A cis bond puts a kink in the long-chain
hydrocarbon tail, while a trans fatty acid is like that of a saturated fatty acid in its
fully extended conformation. It’s also important to note that these double bonds
are isolated from one another by several single bonds, and fatty acids don’t
normally have linked double-bond systems. The notation used for fatty acids
indicates the number of carbon atoms and the number of double bonds. In this
system, 18:0 denotes an 18-carbon saturated fatty acid with no double bonds,
and 18:1 denotes an 18-carbon fatty acid with one double bond.
The melting point of a substance is the state in which both liquid and solid phase
are at an equilibrium. Compared to unsaturated fatty acids, saturated fatty acids
are stretched, therefore they have stronger intermolecular interactions, and it
takes more energy to change the phase from a solid to a liquid. Therefore, a
longer chain length results in a greater melting point.
Unsaturated fatty acids have lower melting points than saturated fatty acids.
They have lower density since they are more unstacked due to presence of kinks
in double bonds.
Glycerol is a simple compound that contains three hydroxyl groups. When all
three of the alcohol groups form ester linkages with fatty acids through
esterification, the resulting compound is a triacylglycerol, formerly triglyceride.
Note that The polar portion of the molecule is represented by the three ester
groups, while the nonpolar portion is represented by the fatty acid tails. It is usual
for three different fatty acids to be esterified to the alcohol groups of the same
glycerol molecule.
Fats and oils are typical lipids in terms of their solubility. A triglyceride is called a
fat if it is a solid at 25 degrees Celsius and it is called an oil if it is liquid at 25
degrees Celsius temperature. These variations in melting points show the
differences between the constituent fatty acids in terms of chain length and
degree of unsaturation. Animals frequently contain fats, which are made up of
saturated fatty acids and are typically solid at normal temperature. Oils are
typically found in plants and, due to their unsaturation, are liquid at room
temperature.
With the use of acids or bases as catalysts, the same hydrolysis reaction can
occur outside of living things. When a base like sodium hydroxide or potassium
hydroxide is used, the process is known as saponification, and the products are
glycerol and the sodium or potassium fatty acid salts.
Fatty acids are usually monoprotic acids (an acid that will only donate 1 proton)
with only one carboxyl group able to form an ester bond, but phosphoric acid is
triprotic and thus can form more than one ester linkage. Phosphatidyl esters
are formed when phosphoric acids form ester bonds both to glycerol and to some
other alcohol.
The nature of the fatty acids in the molecule can vary widely. All these
compounds have long, nonpolar, hydrophobic tails and polar, highly hydrophilic
head groups and thus are markedly amphipathic. In a phosphoacylglycerol, the
polar head group is charged, because the phosphate group is ionized at neutral
pH. A positively charged amino group is also frequently contributed by an amino
alcohol esterified to the phosphoric acid. Phosphoacylglycerols are important
components of biological membranes.
Sphingolipids do not contain glycerol, but they do contain the long-chain amino
alcohol sphingosine. Sphingolipids are found in both plants and animals; they are
particularly abundant in the nervous system.
Frequently, ceramides are the parent compounds for glycolipids. The glycosidic
bond is formed between the primary alcohol group of the ceramide and a sugar
residue, in most cases it is glucose or galactose, this results in a compound
called cerebroside. As the name indicates, cerebrosides are found in nerve and
brain cells, primarily in cell membranes.
Steroids are compounds with widely differing functions but have the same
general structure, a fused-ring system which consists of three six-membered
rings, the A, B, and C rings) and one five-membered ring, the D ring. There are
many important steroids, including sex hormones. Cholesterol is also an example
of a steroid. The only hydrophilic group in the cholesterol structure is the single
hydroxyl group. As a result, the molecule is highly hydrophobic. Cholesterol is
widespread in biological membranes, especially in animals, but it does not occur
in prokaryotic cell membranes. The presence of cholesterol in membranes can
modify the role of membrane-bound proteins. Cholesterol has a number of
important biological functions, including its role as a precursor of other steroids
and of vitamin D3.
Estradiol is an estrogen steroid hormone and the major female sex hormone. It
plays a role in controlling the menstrual and estrous cycles in females. The
growth of secondary female sexual traits including the breasts, widening of the
hips, and a pattern of fat distribution exclusive to women are all brought on by
estradiol. During puberty, adulthood, and pregnancy, it is crucial for the growth
and maintenance of female reproductive structures such the mammary glands,
uterus, and vagina.
Every cell has a cell membrane or a plasma membrane; eukaryotic cells also
have membrane-enclosed organelles, such as nuclei and mitochondria. The
molecular basis of the membrane’s structure lies in its lipid and protein
components. It separates cells from the external environment (protection through
compartmentalization). It also plays an important role in regulation of what goes
in and out of cells. A number of important enzymes are found in membranes and
depend on this environment for their function.
Ampiphatic molecules are pretty useful and versatile due to their hydrophobic
and hydrophilic regions. In an aqueous environment, these molecules organize
into a bilayer structure in which hydrophilic ends are on the outside and
hydrophobic ends inward. This forms the very foundation of the cell membrane.
20. Discuss how the degree of unsaturation of the fatty acid components of
phosphoglycerides affects membrane fluidity.
The arrangement of the hydrocarbon interior of the bilayer can be ordered and
rigid or disordered and fluid. The bilayer’s fluidity depends on its composition. In
saturated fatty acids, a linear arrangement of the hydrocarbon chains leads to
close packing of the molecules in the bilayer, and thus to rigidity. Unsaturated
fatty acids have a kink in the hydrocarbon chain that does not exist in saturated
fatty acids. The kinks cause disorder in the packing of the chains, which makes
for a more open structure than would be possible for straight saturated chains.
When heat is introduced, ordered bilayers become less ordered; bilayers that are
comparatively disordered become even more disordered. This cooperative
transition takes place at a characteristic temperature, like the melting of a crystal,
which is also a cooperative transition. . The transition temperature is higher for
more rigid and ordered membranes than it is for relatively fluid and disordered
membranes
The presence of cholesterol may also enhance order and rigidity. The fusedring
structure of cholesterol is itself quite rigid, and the presence of cholesterol
stabilizes the extended straight-chain arrangement of saturated fatty acids by van
der Waals interactions. Furthermore, the presence of cholesterol is characteristic
of animal, rather than plant, membranes. As a result, animal membranes are less
fluid (more rigid) than plant membranes, and the membranes of prokaryotes,
which contain no appreciable amounts of steroids, are the most fluid of all.
23. Explain how the natural lipid bilayer asymmetry affects possible membrane
composition (bulkier molecules are found in the outer layer)
The distribution of lipids is not the same in the inner and outer portions of the
bilayer. Because the bilayer is curved, the molecules of the inner layer are more
tightly packed. Bulkier molecules, such as cerebrosides tend to be located in the
outer layer.
Integral proteins are found within the lipid bilayer. Removing integral proteins
from membranes is much more difficult. It is any protein which has a special
functional region for the purpose of securing its position within the cellular
membrane. In other words, an integral protein locks itself into the cellular
membrane.
Lipid-anchored proteins is a point of attachment in which proteins anchored to
the lipids via covalent bonds from cysteines or free amino groups on the protein
to one of the several lipid anchors.
26. List the three main functions of membranes and membrane proteins.
The three main functions of membranes and membrane proteins are transport,
receptor, and catalysis.
30. Explain how the rate of transport against a concentration gradient can be
used to elucidate a facilitated diffusion mechanism.
37. Explain the important role of vitamin A in the primary chemical reaction of
vision.
When rhodopsin is active (that is, when it can respond to visible light), the double
bond between carbon atoms 11 and 12 of the retinal (11-cis-retinal) has the cis
orientation. Under the influence of light, an isomerization reaction occurs at this
double bond, producing an all-trans retinal. Because the all-trans form of retinal
cannot bind to opsin, alltrans-retinal and free opsin are released. As a result of
this reaction, an electrical impulse is generated in the optic nerve and
transmitted to the brain to be processed as a visual event. The active form of
rhodopsin is regenerated by enzymatic isomerization of the all-trans-retinal back
to the 11-cis form and subsequent re-formation of the rhodopsin.
38. Explain the important role of vitamin D in the regulation of calcium and
phosphorus.
The several forms of vitamin D play a major role in the regulation of calcium and
phosphorus metabolism. Vitamin D3 is formed from cholesterol by the action of
ultraviolet radiation from the sun. It is further processed in the body to form
hydroxylated derivatives, which are the metabolically active form of this particular
vitamin.