BCH 401

BIOSYNTHESIS OF
MACROMOLECULES
 Lipids
❖ Lipids are class of biological compounds that are insoluble
in water (i.e. non-polar or hydrophobic) but soluble in
organic solvents.

❖ Lipids are formed mainly from alcohol and fatty acids

combined together by ester linkage.

O
H2O O
R CH2 OH HO C R R CH2 O C R
+
Fatty alcohol Fatty acid Esterase (lipase) ester (lipid)
 Functions of Lipids
❖The functions of lipids include:
▪Energy storage
▪Major component of cell membranes
▪Important in cell signaling as steroid
hormones and messenger molecules.
 Major Classes of Lipids
❖Fatty acids
❖Triacylglycerol
❖Phospholipids
❖Glycolipids
❖Sterols (i.e. cholesterol)
 Fatty Acids
❖ The simplest lipids are fatty acids.
❖ Fatty acids are long hydrocarbon chains (16 or 18 carbons) with a
carboxyl group (COO–) at one end.
❖ Have the general formula R-(CH2)n-COOH and mostly have straight
chain (a few exceptions have branched and heterocyclic chains).
▪ In this formula "n" is mostly an even number of carbon atoms
(2-34) with a few exceptions that have an odd number.
❖ They can be classified as saturated or unsaturated
5
 Fatty Acids Contd.
❖ Saturated fatty acids
▪ contain single bonds in the hydrocarbon chain.
▪ solid at room temperature because their aliphatic chain allows
molecules to be packed in a parallel alignment.
▪ interactions between neighboring chains are weak.
❖ Unsaturated fatty acids
▪ have one or more double bonds in the chain.
▪ liquid at room temperature because the cis double bonds
interrupt the packaging of chains. 6
 Fatty Acids Contd.
❖ A 16-C fatty acid: CH3(CH2)14-COO-
Non-polar polar

❖ A 16-C fatty acid with one cis double bond between C atoms 9-10
may be represented as 16:1 cis ∆9.
❖ Some fatty acids and their common names:
14:0 myristic acid; 16:0 palmitic acid; 18:0 stearic acid;
18:1 cis ∆9 oleic acid
18:2 cis ∆9,12 linoleic acid
18:3 cis ∆9,12,15 a-linonenic acid
20:4 cis ∆5,8,11,14 arachidonic acid
20:5 cis ∆5,8,11,14,17 eicosapentaenoic acid (an omega-3) 7
 Structure of Fatty Acids

❖ Palmitate and Stearate are saturated fatty acids while oleate is

unsaturated.
 Triacylglycerol
❖ Fatty acids are stored as triacylglycerols, or fats: three fatty
acids linked to a glycerol molecule.
 Phospholipids
❖ Phospholipids are principal components of cell membranes;
consist of two fatty acids joined to a polar head group.

❖ All phospholipids are amphipathic molecules; they have

hydrophobic tails and hydrophilic head groups.

▪ Glycerol phospholipids: the fatty acids are bound to glycerol.

The third carbon of glycerol is bound to a phosphate group,
which is often bound to another polar group.
Structure of Phospholipids
Structure of Phospholipids Contd.
 Glycolipids
❖ Glycolipids are also part of membrane lipids. They consist of two
hydrocarbon chains and a carbohydrate polar head group (amphipathic).
 Cholesterol
❖ Cholesterol is the lipid responsible for the fluidity of membranes.

❖ Cholesterol consists of four hydrophobic hydrocarbon rings and a polar

hydroxyl (OH) group (amphipathic).