Professional Documents
Culture Documents
• Introduction
• Biochemistry of Amino Acids
• Biochemistry of Proteins
• Portrait of Allosteric Protein
• Enzymes
Outline
• Biochemistry of Carbohydrates
• Glycoproteins and Glycosaminoglycan
• Biochemistry of Lipids
• Biological Membranes
• Bioenergetics and Oxidative
Phosphorylation
• Basic Concepts of Metabolism
Outline
• Biochemistry of Carbohydrates
• Glycoproteins and Glycosaminoglycan
• Biochemistry of Lipids
• Biological Membranes
• Bioenergetics and Oxidative
Phosphorylation
• Basic Concepts of Metabolism
Biochemistry of Lipids
:Objectives
”Recognize the features and Functions of different classes of “Lipids -
Understand the nomenclature and the physical properties of fatty acids and the relation -
.of these properties to the saturation state of the fatty acids
.Recognize the structure and the function of different classes polar lipids -
.Recognize the structure most popular examples for each class of lipids -
Understand the role lipids as pigments, signals and cofactors, knowing different -
examples
Classification
1. Storage lipids.
2. Structural lipids in membranes.
3. Lipids as signals, cofactors and pigments.
Storage Lipids
Fatty acids are hydrocarbon derivatives.
- C4 to C36.
- Saturation.
- Nomenclature.
- Physical properties.
Triacylglycerols.
- Simple vs. complex triglycerides.
- Functions: provide stored energy and insulation.
Waxes.
- Functions: serve as energy stores and water repellents
Structural Lipids
Types of membrane lipids:
1. Glycerophospholipids:
- Phosphatidic acid.
2. Sphingolipids:
- Sphingosine.
3. Sterols:
- Steroid nucleus.
- Functions.
Lipids as signals, cofactors and pigments
References
Chap. 11 of Lehninger
Lipids
Defined on the basis of solubility.
Lipids: heterogeneous group of water insoluble
(hydrophobic) organic molecules,
they are chemically diverse compound but
have one feature: water insoluble
1. Storage lipids
Triglycerides, Waxes and Fatty acids.
Triglycerides
Fats and oils are stored forms of energy and are derivatives of
fatty acids.
- Leukotrienes.
lysophosphatidic acid (LPA)
sphingosine-1-phosphate (S1P)
platelet activating factor (PAF)
- Steroid hormones carry messages between tissues.
anandamide or arachidonoyl ethanolamine (AEA)
Fatty acids (F.A) are carboxylic acids with long hydrocarbon chain ranging from 4-36
carbon atom 16- and 18-C long are most abundant.
-Even number of carbons, 16, 18… the odd are also present but rare.
-the hydrocarbon chain can be fully saturated (without double bonds), or with one, two or
three double bonds (cis-configuration only)
• The delta system numbers the double bonds from the carboxyl group (the α
carbon), specify the chain length and the number of
double bonds separated by colon
Palmitic acid is saturated F. A with 16 C atoms 16:0
Stearic acid 18:0
9
Molecular structure Name
Lauric acid: saturated C12
*The carboxyl group is polar and this accounts for the slight solubility of
short chain fatty acid in water
*The longer the fatty acid acyl and fewer the double bonds, the lower is the
solubility in water
Melting points
melting points are strongly influenced by the length and degree of unsaturation
at R.T the saturated F. A with length chain 12-24 have waxy consistency while
the unsaturated F. A are liquid
fully saturated molecule
free rotation around each C-C
This gives the hydrocarbon
chain great freedom and
flexibility Saturated chains pack
adopt the most stable tightly and form more
conformation which is the rigid, organized
fully extended form in which aggregates
the steric hindrance of
neighboring atoms is minimized
The molecules can pack together
tightly in nearly crystalline arrays.
So the Vander Waal interaction
and the hydrophobic interaction
are maximized
High thermal energy required to
disorder (melt) these highly
ordered F.A molecules higher
melting points
In the unsaturated F. A
the cis configuration
double bond forces a kink
(bend) in the hydrocarbon
chain
Unsaturated chains bend
and pack in a less ordered
way, with greater potential
for motion
The saturated F.As take high thermal energy required The unsaturated F.As take less thermal energy to
to disorder (melt) these highly ordered disorder these poorly ordered arrays of
F.A molecules higher melting points unsaturated F.As they have lower melting points
Triacylglycerols or Triglycerides
Fatty acid triesters of glycerol
Most contain two or three different types
of fatty acid residues
*Two advantages for using the triglycerides as stored fuel rather than
polysaccharides as glycogen and starch:
1- the carbon atoms of F.A are more reduced than that of carbohydrates
oxidation of triglycerides yields more than twice as much energy (gm/gm) as the
oxidation of CHO ( F.A 9 Kcal, CHO 4 Kcal).
2- triglycerides are hydrophobic unhydrated, the organism that carries fat as
fuel does not have to carry the extra weight of water of hydration that is
associated with stored polysaccharides (2gm water/1gm polysaccharides).
Fats function as energy reservoirs in animals
The fat content of normal humans allows them to survive starvation for 2 or 3
months
While human store of glycogen can supply only for one day but carbohydrates
are quick sources for metabolic energy because of water solubility
* Exposure of the lipid rich food to oxygen for long time may spoil and the
lipid is said to be Rancid. Rancidity results from the cleavage of double bond in
unsaturated F. A that produce aldehyde and carboxylic acid with low M.wt
bad smell
Waxes serve as energy store and water repellents
Biological waxes are esters of
• long chain (C14-C36) saturated and unsaturated fatty acid
• with long chain alcohol (C16-C30)
• melting points about 60-100 ºC
C14-C36 sat. & unsat. F.A C16-C30 long chain alcohol
Biological membranes
feature: double layer of lipid
act as barrier to the passage
of polar molecules and ions.
Amphipathic: one end of the
molecule is hydrophobic and
the other is hydrophilic
Platelet activating
factor: released from
leukocyte (basophiles)
and stimulate platelet
aggregation and the
release of serotonin
B- Ganglioside: the most complex glycolipid, have oligosaccharide as their polar head groups
and one or more residues of Sialic acid
Ganglioside are primarily components of membranes on cell surfaces and constitute 6% of
brain lipids
Sphingolipids: act as a site of biological recognition,
act as receptors for hormones and glycoproteins
3-Sterols
Structural lipids present in the
membranes of some eukaryotic cells.
Characterized by the steroid nucleus
consisting of four fused rings three
rings with 6 C atoms and one ring with 5
C atoms, the steroid nucleus is relatively
rigid and planar
Cholesterol is the major sterol in animal
tissues and it is amphipathic with a polar
head (the –OH group), and the non-polar
body is the steroid nucleus
Similar sterols are present in
eukaryotes: Stigmasterol plants
Ergosterol fungi
Functions
- Membrane constituents
- Precursors of different product with vital biological activities (steroidal
hormones that regulate the gene expression)
- Bile acids are derivatives of cholesterol that act as emulsifying agent in the
intestine
Lipids as Signals, cofactors and pigments
Group of lipids present in small amounts play various essential function
- Have active roles in metabolic processes as metabolite and messenger
- Potent signals and hormones carried in the blood from one tissue to others
- Intracellular messengers generated to response to outer signal
- Can function as cofactors
- Pigments
- Fat soluble vitamins
Vit K1 (Phylloquinone)
The End
A Lipid Bilayer Model of Cell Membrane Structure
An acyl compound is a compound that has a carbon doubled bonded
to an oxygen (C=O) in its molecule.