MACROMOLECULES BCH 101

BIOMOLECULES
This refers to biological molecules
Hydrogen, oxygen, carbon, and nitrogen constitute more than 99% of
the atoms in the human body, with most of the H and O occurring as
H2O.
It is the ability of these elements to form covalent bonds by electron-pair
sharing. They form the strong covalent bonds.
Two other covalent bond-forming elements, phosphorus and sulfur, also
play important roles in biomolecules.
The strength of covalent bonds is inversely proportional to the atomic
weights of the atoms involved, H, C, N, and O form the strongest
covalent bonds.
CARBON AS THE BACKBONE
All biomolecules contain carbon. The prevalence of C is due to its
unparalleled versatility in forming stable covalent bonds.
Carbon can form as many as four such bonds by sharing each of the
four electrons in its outer shell with electrons contributed by other atoms.
Hydrogen can form one such bond by contributing its single electron to
formation of an electron pair.
Oxygen, with two unpaired electrons in its outer shell, can participate in
two covalent bonds.
Nitrogen, which has three unshared electrons, can form three such
covalent bonds.
BIOMOLECULAR HIERARCHY
The major precursors for the formation of biomolecules are water,
carbon dioxide, and three inorganic nitrogen compounds—ammonium
(NH4 ), nitrate (NO3), and dinitrogen (N2).
These biomolecules are converted to simple organic compounds called
metabolites that are intermediates in cellular energy transformation
and in the biosynthesis of various sets of building blocks: amino acids,
sugars, nucleotides, fatty acids.
Covalent linkage of these building blocks form macromolecules e.g
Polysaccharide, proteins, lipids, polynucleotides (RNA and DNA).
Interactions among macromolecules lead to the next level of structural
organization called supramolecular complexes.
Inorganic precursors

Metabolites e.g pyruvate

Building blocks e.g glucose

Macromolecules e.g proteins

Organelles e.g nucleus

Cell

Supramolecules e.g multi-enzyme

CARBOHYDRATES
Carbohydrates are the single most abundant class of organic molecules
found in nature.
The name carbohydrate arises from the basic molecular formula (CH2O)n,
which can be rewritten (C . H2O)n to show that these substances are
hydrates of carbon, where n 3 or more.
Carbohydrates constitute a versatile class of molecules. Energy from the sun
captured by green plants, algae, and some bacteria during photosynthesis
is stored in the form of carbohydrates.
In turn, carbohydrates are the metabolic precursors of virtually all other
biomolecules.
Breakdown of carbohydrates provides the energy that sustains animal life.
Carbohydrates are covalently linked with a variety of other molecules.
Carbohydrates linked to lipid molecules, or glycolipids, are common
components of biological membranes.
Proteins that have covalently linked carbohydrates are called
glycoproteins.
These two classes of biomolecules, together called glycoconjugates, are
important components of cell walls and extracellular structures in plants,
animals, and bacteria.
In addition to the structural roles such molecules play, they also serve in
a variety of processes involving recognition between cell types.
Recognition events are important in normal cell growth, fertilization,
transformation of cells, and other processes.
FEATURES OF CARBOHYDRATES
(1) the existence of at least one and or more asymmetric centers
(2) the ability to exist either in linear or ring structures
(3) the capacity to form polymeric structures via glycosidic bonds
(4) the potential to form multiple hydrogen bonds with water or other
molecules in their environment.
Carbohydrates are polyhydroxy aldehydes or ketones, or substances
that yield such compounds on hydrolysis.
CLASSES
Monosaccharides, or simple sugars, consist of a single polyhydroxy
aldehyde or ketone unit. They cannot be hydrolysed into simpler
carbohydrates e.g glucose, fructose.
Oligosaccharides consist of short chains of monosaccharide units, or
residues, joined by characteristic linkages called glycosidic bonds. The
most abundant are the disaccharides, with two monosaccharide units e.g
maltose, sucrose.
The polysaccharides are sugar polymers containing more than 20 or so
monosaccharide units, and some have hundreds or thousands of units.
They are polymers of simple sugars or their derivatives e.g cellulose.
PROTEIN
Proteins are the most abundant biological macromolecules, occurring in all
cells and all parts of cells.
Proteins also occur in great variety; thousands of different kinds, ranging in
size from relatively small peptides to huge polymers.
They also exhibit enormous diversity of biological function and are the most
important final products of the information pathways.
All proteins, are constructed from the same ubiquitous set of 20 amino acids,
covalently linked in characteristic linear sequences.
Cells can produce proteins with very different properties and activities by
joining the same 20 amino acids in different combinations and sequences.

MI KAZEEM, PHD 10
AMINO ACIDS
Proteins are polymers of amino acids, with each amino acid residue joined to
its neighbour by a specific type of covalent bond.
Proteins can be broken down (hydrolyzed) to their constituent amino acids by a
variety of methods.
The first to be discovered was asparagine, in 1806. The last of the 20 to be
found, threonine, was not identified until 1938.
Asparagine was first found in asparagus, and glutamate in wheat gluten;
tyrosine was first isolated from cheese (its name is derived from the Greek
tyros, “cheese”); and glycine (Greek glykos, “sweet”) was so named because
of its sweet taste.

MI KAZEEM, PHD 11
STRUCTURES OF AMINO ACIDS
The structure is a tetrahedral alpha carbon (C), which is covalently linked to
both the amino group and the carboxyl group.
Also bonded to this carbon is a hydrogen and a variable side chain. It is the
side chain, the so-called R group, that gives each amino acid its identity.

In addition to these 20 amino acids there are many less common ones.
Because the resulting amino acid contains one positive and one negative
charge, it is a neutral molecule called a zwitterion.

MI KAZEEM, PHD 12
STRUCTURES (CONTD)

Amino acids are also chiral molecules because the α-carbon is bonded to four
different molecules (except in glycine).
With this four different molecules attached to it, the α-carbon is said to be
asymmetric.

The two possible configurations for the α-carbon constitute non-identical mirror
image isomers or enantiomers.
All molecules with a chiral center are also optically active—that is, they rotate
plane-polarized light i.e laevo or dextro.

MI KAZEEM, PHD 13
ABBREVIATIONS

MI KAZEEM, PHD 14
PROTEIN CLASSIFICATION
Simple proteins contain only amino acid residues and no other chemical
constituents.
Conjugated proteins contain permanently associated chemical components in
addition to the amino acid.
The non–amino acid part of a conjugated protein is usually called its
prosthetic group.
Conjugated proteins are classified on the basis of the chemical nature of their
prosthetic groups.
Lipoproteins contain lipids e.g lipoproteins
Glycoproteins contain carbohydrates e.g Immunoglobulin G
Metalloproteins contain specific metals e.g Ferritin
MI KAZEEM, PHD 15
LIPIDS
The biological functions of the lipids are as diverse as their chemistry.
Fats and oils are the principal stored forms of energy in many organisms.
Phospholipids and sterols are major structural elements of biological
membranes.
Other lipids, although present in relatively small quantities, play crucial roles
as enzyme cofactors, electron carriers
The fats and oils used almost universally as stored forms of energy in living
organisms are derivatives of fatty acids.
There are two major classes of lipids: Storage (e.g triacylglycerol) and
structural lipids (e.g phospholipids)
FATTY ACIDS
Fatty acids are carboxylic acids with hydrocarbon chains ranging from 4 to 36
carbons long (C4 to C36).
In some fatty acids, this chain is unbranched and fully saturated (contains no
double bonds); in others the chain contains one or more double bonds.
The most commonly occurring fatty acids have even numbers of carbon atoms
in an unbranched chain of 12 to 24 carbons.
The physical properties of the fatty acids, and of compounds that contain
them, are largely determined by the length and degree of unsaturation of the
hydrocarbon chain.
The nonpolar hydrocarbon chain accounts for the poor solubility of fatty acids
in water.
EXAMPLES
TRIACYLGLYCEROL
The simplest lipids constructed from fatty acids are the triacylglycerols, also
referred to as triglycerides, fats, or neutral fats.
Triacylglycerols are composed of three fatty acids each in ester linkage with a
single glycerol.
Those containing the same kind of fatty acid in all three positions are called
simple triacylglycerols and are named after the fatty acid they contain. E.g
tristearin, tripalmitin, and triolein.
Most naturally occurring triacylglycerols are mixed; they contain two or more
different fatty acids.
Triacylglycerol provides stored energy. This is why many foods contain
triacylglycerol.
NUCLEIC ACIDS
Nucleotides and nucleic acids are biological molecules that possess
heterocyclic nitrogenous bases as principal components of their structure.
The biochemical roles of nucleotides are numerous; they participate as
essential intermediates in virtually all aspects of cellular metabolism.
Nucleic acids, on the other hands, are the elements of heredity and the agents
of genetic information transfer.
The two basic kinds of nucleic acids are deoxyribonucleic acid (DNA) and
ribonucleic acid (RNA).
Complete hydrolysis of nucleic acids liberates nitrogenous bases, a five-carbon
sugar, and phosphoric acid in equal amounts.
NITROGENOUS BASES
The bases of nucleotides and nucleic acids are derivatives of either
pyrimidine or purine.
The common naturally occurring pyrimidines are cytosine, uracil, and thymine
(5-methyluracil).
Cytosine and thymine are the pyrimidines typically found in DNA, whereas
cytosine and uracil are common in RNA.
Various pyrimidine derivatives, such as dihydrouracil, are present as minor
constituents in certain RNA molecules.
Adenine (6-amino purine) and guanine (2-amino-6-oxy purine), the two
common purines, are found in both DNA and RNA.
Other naturally occurring purine derivatives include hypoxanthine, xanthine,
and uric acid
PENTOSES
Pentoses are five-carbon sugars.
RNA containns the pentose D-ribose, while 2-deoxy-D-ribose is found in DNA.
Nucleosides are compounds formed when a base is linked to a sugar via a
glycosidic bond
Nucleosides are named by adding the ending –idine to the root name of a
pyrimidine or -osine to the root name of a purine.
The common nucleosides are thus cytidine, uridine, thymidine, adenosine,
and guanosine.
Nucleosides are much more water-soluble than the free bases because of the
hydrophilicity of the sugar moiety.
NUCLEOTIDES
A nucleotide results when phosphoric acid is esterified to a sugar -OH group
of a nucleoside.
The vast majority of monomeric nucleotides in the cell are ribonucleotides
having 5-phosphate groups.
Example are adenosine 5-monophosphate, guanosine 5-monophosphate,
cytidine 5-monophosphate, and uridine 5- monophosphate.
These compounds are more often referred to by their abbreviations: 5-AMP,
5-GMP, 5-CMP, and 5-UMP, or even more simply as AMP, GMP, CMP, and
UMP.
STRUCTURES