Condensation

and Hydrolysis
Condensation - basic principles

The term monomer is given to single (smaller, simple) sub-units from which (larger, complex) molecular
stuctures called polymers are built up by condensation.
Condensation is a chemical process by which 2 molecules are joined together to make a larger, more
complex,
molecule,
with
the
loss
of
water.
It is the basis for the synthesis of all the important biological macromolecules (carbohydrates,
proteins,
lipids,
nucleic
acids)
from
their
simpler
sub-units.
It is important not to get condensation and hydrolysis muddled up, as they are in fact opposite
processes! Condensation is so called because the product is drawn together from two other substances,
in effect getting smaller by losing water. It does not give off water to condense and run down the
window!
In all cases of condensation, molecules with projecting -H atoms are linked to other molecules with
projecting -OH groups, producing H 2O, ( H.OH ) also known as water, which then moves away from the
original molecules.
A-H + B-OH
--> A-B
+ H 2O

More details:

In each of the cases below, some details are included in order to show the similarities which explain
the basic processes of condensation and hydrolysis, as well as some other features which are specific
to the categories of compounds, and which may be covered in the later sections of the syllabus
specification. In the cases of condensation reactions below, you are not expected to know all the
background details. For example, in each case specific enzymes are involved ( names unimportant - mostly
synthetases), as well as activation energy in the form of ATP (because simple molecules do not
spontaneously
join
together
to
become
more
complex
or
ordered).
In carbohydrates, the sub-units to be joined are monosaccharides like glucose. Both of the groups
which combine are -OH groups, (even though there are many single -H atoms on a glucose molecule).
Joining two -OH groups with the removal of H 2 O results in a disaccharide containing an
-O- bridge
between the 2 monosaccharide units. Between glucose units, these bonds are usually between carbon 1 of
one glucose molecule and carbon 4 or 6 on the other. Depending on the direction of the -OH group at
carbon 1, it may be called an alpha or a beta linkage. The bond so formed is called a glycosidic bond
or link. These links can be extended many times, resulting in the production of polysaccharides.
In proteins, the sub-units to be joined are amino-acids. The -H comes from -NH 2 (the amino, or amine,
group) and the -OH comes from -COOH (the carboxylic acid group) at the end of another amino acid
molecule. As a result, a peptide bond (- CONH-) is formed between the two amino acids, and the product
is called a dipeptide. These links can also be extended many times, resulting in the production of
polypeptides. A protein is effectively formed when a polypeptide chain re-organises itself into a
specific
shape.
In lipids (fats and oils) glycerol provides up to three -OH groups (it is actually a triple alcohol)
to react with -COOH (carboxylic acid groups) on so-called fatty acids. Once again this results in -Obridges forming between the glycerol and each fatty acid chain. The links so formed are called ester
bonds.
Glycerol attached to one fatty acid chain is called a monoglyceride; glycerol molecules with two fatty
acid chains are diglycerides, glycerol with three attached fatty acid chains are triglycerides. A
similar ester bond can be used to attach a single group containing phosphate, resulting in a
phospholipid.
Since the maximum number of fatty acid chains or other groups which can be attached to glycerol is 3,
there is no way that lipids can be continually added to like polysaccharides and polypeptides.
In
nucleic
acids,
there
is
a
similar
but
somewhat
more
complex
situation.
Different nucleotides (each composed of a base, pentose sugar and a phosphate group) are joined by
condensation reactions to form DNA and RNA. The outer sections of the DNA double helix are composed of
the pentose sugar deoxyribose alternating with phosphate groups held together with special ester links
(phosphodiester bonds). In DNA replication, each new strand that forms is built up from nucleotides
according
to
base
pairing
rules
and
joined
by
repeated
condensation
reactions.
In RNA there is a single strand, this time of the pentose sugar ribose (each attached to a base)
alternating with phosphate groups but also held together by phosphodiester bonds. In transcription,
messenger RNA is built up from individual RNA nucleotides corresponding (by slightly different base
pairing rules) to a section of the DNA template molecule. These nucleotides become joined together in a
row
by
condensation
reactions.
The linkages between nucleotides can effectively be extended to a large extent, resulting in
polynucleotide
chains.
The covalent and fairly permanent covalent linking of pentose sugars to bases also involves a
condensation reaction, but this does not regularly become made and unmade by condensation and hydrolysis
in
the
same
way
as
links
in
the
side
units.
The much weaker bonding between base pairs (caused by hydrogen bonds) does not involve the sort of
condensation reaction already mentioned.

Hydrolysis - basic principles

Hydrolysis is the opposite to condensation. A large molecule is split into smaller sections by breaking
a
bond,
adding
-H
to
one
section
and
-OH
to
the
other.
The products are simpler substances. Since it involves the addition of water, this explains why it is
called hydrolysis, meaning splitting by water.
A-B
+ H 2O --> A-H + B-OH

Do not confuse this involvement of water in hydrolysis with making a solution, in which the role of
water is to act as a solvent, rather than taking part in a chemical reaction. (Hydration is yet another
completely different process, involving the addition of water, but not breaking of bonds.)
Also do not assume that this breakdown releases energy, which is usually produced when the simpler
substances
are
oxidised
in
respiration.
Incidentally, all (food) digestion
often not appreciated. Generally
proteases, lipases, nucleases,
In fact the main information which
opens.

reactions are examples of hydrolysis, and the involvement of water is

these reactions are controlled by enzymes such as carbohydrases,
more specific examples of which are fairly well known.
is expected to be known is the type of enzyme and the bonds which it

However, hydrolysis can also be achieved as a result of the action of acids (usually accompanied by
heat) on complex carbohydrates (polysaccharides, etc) and proteins (including polypeptides, etc).

More details

Carbohydrases
Amylase breaks down starch (both amylose and the straight chain ections of amylopectin) into maltose (a
disaccharide composed of 2 glucose units linked by 1 alpha 4 glycosidic bonds) by adding -H and -OH from
water
across
the
glycosidic
bonds.
Maltase then completes the hydrolysis process, splitting each maltose molecule into two glucose
molecules.
Sucrase (also known as invertase) breaks down sucrose, producing glucose and fructose.
Lactase (beta galactosidase) breaks down lactose, breaking bonds between galactose and glucose.
Proteases
Exopeptidases break open peptide bonds between amino acids, starting at the end of the polypeptide chain
(
and
working
along
the
polypeptide
chain
to
the
next
).
Endopeptidases break open bonds between amino acids, starting somewhere in the middle of the polypeptide
chain (perhaps at a specific amino acid sequence).
Lipases
Lipases break ester bonds between glycerol and fatty acids, or phosphate groups.

Molecular
structure
of
glucose
and
other
carbohydrates
To the right of this page I have put a number of links to other files on this website showing molecules

of carbohydrates, which offer the opportunity to see and interact with these molecular models in 3
dimensions.
Glucose is an example of a carbohydrate which is commonly encountered. It is also known as blood sugar, and dextrose.
Its chemical formula is C 6H12O6, and this empirical formula is shared by other sugars - called hexoses - 6 carbon sugars. You may
wish to know in some detail how these 24 atoms are arranged in the molecule of glucose the structural formula.
In some books you may see diagrams of the glucose molecule looking like this: This so-called stick diagram really only describes
how things are in dry (powder) glucose.

In life - in your blood and inside cells of plants and

animals - most of the glucose consists of molecules
shaped into a ring (actually a 6-sided figure, a
hexagon) which may be drawn with this fairly
simple format:
Note that there is an oxygen atom forming part of
the ring, and that there are simple lines drawn
making up the rest of the ring, and a section sticking
out to one side. These lines represent carbon atoms,
and -H and -OH groups, most of which have been
left out for simplicity. Sometimes the details of just
some of these -H and -OH groups are drawn in at
one end (or both ends). This is because the
orientation of these groups slightly alters the
chemistry of the molecule, so the resulting
molecules are given different names.
alpha
glucose
beta
glucose
In alpha glucose the -H
group of the rightmost
Carbon atom (C1) is
above the plane of the
ring, whereas it projects
below the ring in beta
glucose.
There are in fact 3
versions of the ring
structure called chairs and
boat, depending on the
bending in or out of the
left and right corners, but
it is easier to draw it as a
flat hexagon. Some of the
lines may be thickened or
flared out to give an
impression
of
3D
structure on the page
All the other groups can vary in different
hexose sugars, which result in slightly
different chemical properties.
It is worth knowing the numbers used to
describe each of the 6 carbon atoms.
This numbering is important when glucose
units are joined together.
1-4 linkages (formed by glycosidic
bonding) result in a simple linear (end to
end) connection, which is found in maltose,
a disaccharide:
Repeating
the
condensation
process
will result in the
polysaccharide starch,
which is considered to
have
2
components,
amylose
and
amylopectin. The chain
of 1-4 linkages so
formed can be quite
long, and may wind up
into a helix. This is
the
situation
in
amylose, (a linear part
of
which
is
shown
here):

On the other hand, 1-6 linkage causes the formation of a branching point which then allows another chain
of 1-4 linkages to develop. This 3-D branching also produces other points at which glucose may be added
by condensation or removed by hydrolysis. This branching occurs in amylopectin, (a small section of
which is shown here):
This basically explains the structure of starch and
glycogen.