Sugars

and Lipids (Lecture 6):

Sugar functions: energy storage, building block for nucleic acids, structural
component (wood).

Disaccharide: table sugar, made of fructose and glucose

The typical structure is a multiple of CH2O, e.g. C3H6O3
You always find two functional groups in a sugar: one carbonyl group and several
hydroxyl groups.

Aldose and ketose are isomers, same formula, but different structure.

Important to keep in mind: all isomers differ in their covalent bonds (that is, optical
isomers also have a different structure).

This can be illustrated by drawing two optical isomers and trying to rotate one to
make it overlap the other. This is impossible, just like your two hands can never
overlap.

Glucose and galactose are two different optical isomers of this 6-carbon sugar.

In solution, straight-chain glucose forms another covalent bond to become the ring
form of glucose. Because this converts C-1 from a symmetric to an asymmetric
carbon atom (C-1 in the ring form has four different groups attached to it, versus 3
in the straight chain form), you can get two glucose isomers, alpha- and betaglucose.

Sugar polymers (polysaccharides) are formed by covalent bonds called glycosidic
linkages between the C-1 of one sugar with any OH-group of the second sugar, but
only two links are interesting to us: alpha1,4 giving rise to maltose and eventually
starch, and beta1,4 giving rise to cellobiose, and eventually cellulose.
In starch, bulky CH2OH groups are all on the same side, bending the polymer
resulting in the shape of a spiral.

On the other hand, the second glucose in cellobiose is flipped (with the CH2OH group
pointing downwards) compared to starch, which has huge structural implications.
You now get a very symmetrical, straight molecule.

Another reminder about structural formulas: they are often simplified by omitting C
and H atoms: each corner corresponds to a carbon atom bonded to 2 hydrogen
atoms if nothing else is indicated.

Lipids: can be all kinds of structures: the only thing they have in common is that
they are insoluble in water.


The most important lipids are fats (solid) and oils (liquid), which consist of three
fatty acids and one glycerol connected by covalent bonds. Fatty acids on their own
have one carboxyl group and a long hydrocarbon chain. Fatty acids are amphiphilic
(hydrophilic carboxyl group plus hydrophobic hydrocarbon chain), and are found in
soap.

Fats provide more energy per weight than starch, but take longer to mobilize; longterm storage.

Phospholipids are also amphiphilic: a hydrophilic head group and two hydrophobic
fatty acid tails attached to glycerol. Phospholipids have the unique capability to selfassemble into lipid bilayers with the hydrophobic fatty acid tails pointing inward
away from water.
To avoid exposed edges, lipid bilayers will assemble into a globular compartment.
This is energetically most favorable, as no more hydrophobic parts are exposed to
water.
No complicated mechanism needed to invoke evolution of a primitive cell enclosed
by a lipid bilayer; phospholipids preferentially assemble into a sealed compartment.

Lipid bilayers (cell membranes) are very fluid, with phospholipids in constant
lateral motion.

Some fatty acids contain double bonds; then they are called unsaturated fatty acids.
Double bonds cause kinks in fatty acid tails. Therefore they cannot be packed as
closely together as straight, saturated fatty acids. This is the reason butter is solid at
room temperature (only straight-chain fatty acids in butter fat), and oils are fluid
(many unsaturated fatty acids: double bonds making kinks).

Unsaturated fatty acids in lipid bilayers increase the fluidity and permeability of the
membrane.

Fish and plants adjust the amount of double bonds in phospholipids to keep
membrane fluidity stable over a wide variety of temperatures.