BIOCHEMISTRY ORGANIC CONSTITUENT OF THE CELLS.
Bio chemistry: is the study of structures, properties and functions of chemical constituents of the cells.
Agriculture; in developing pesticides and herbicides.
Medicine; including all pharmaceuticals.
Chief/ macro elements: hydrogen (H), carbon(C), nitrogen (N), oxygen (O), phosphorous (P), sulphur(S).
Ions – sodium(Na+) , magnesium (Mg2+) , chlorine( cl–) , calcium (Ca2+) etc.
Trace elements – manganese(Mn) , iron(Fe) , cobalt(Co),copper (Cu) , molybdenum(Mo) and iodine(I).
- Polysaccharides( carbohydrates)
- Protein
- Lipids
- Nucleic acids.
They are either simple sugars or compound sugars.
The compound sugars are formed by condensation of simple `sugar molecules.
They are hydrate of carbon from the proportion of hydrogen and oxygen in water.
The basic carbohydrate unit is thus a sugar which is the derivative of a poly hydrosol alcohol.
Alcohol is the paraffin compound with hydrogen atom replaced by the univalent hydroxyl (OH) group.
Paraffin is aliphatic or chain of compounds of carbon and hydrogen in which the carbon atoms are linked by single bonds to adjacent atoms. (see Example above).
The simpler hydroxyls are the glycol and glycerol and the simplest of sugar is the glycerose (glycerin).
The carbohydrate contains several hydroxyl groups.
Some contain aldehyde (-CHO) group and others contain ketone group ( -CO-)
Examples;
Glucose: is a pentahydroxyl alcohol with the aldehyde group.
Fructose: is the pent hydroxyl alcohol with ketone group.
Complex sugars are built from the basic sugar units called monosaccharides through the process of condensation polymerization.
Many sugars are reducing sugars and others are non-reducing sugars but give rise to reducing sugars on hydrolysis with enzymes or mineral acid (mostly dilute HCL)
NB:
Carbohydrates are called reducing sugar because they act as reducing agents supplying electrons from their functional groups i.e. the aldehyde and ketone groups which can reduce the cu2+ ions to cu+ ions which appear orange or yellow ppt (precipitate).
The true carbohydrates are saccharides with a combination of sugar units. These are divided into three main classes
monosaccharides – with a single sugar unit
Disaccharides – with two sugar units.
Polysaccharides- with many sugar units.
SUGAR
Sugar which include mono and disaccharides are all soluble in water. They have a sweet taste.
They are crystalline and small molecules.
Those with a potentially active aldehyde or ketone group are the reducing sugars e.g. glucose.
Sugars without potentially active reducing groups are known as non-reducing sugars e.g. Sucrose (C12H22O11).
Monosaccharides
Trioses have 3 carbon atoms
Tetraoses have 4 carbon atoms
Pentoses have 5 carbon atoms
Hexoses have 6 carbon atoms
Heptoses have 7 carbon atoms
-Of code, hexoses and pentoses are most common and triose being the true sugar.
-Pentose sugars are never occurring but only in combination with other groups
Of compounds.
Riboses- this occurs in one kind of nucleic acid. A derivative of deoxyribose
Hexose. The most important free sugar.
D-glucose
D- Fructose these are the most common sugars.
Structure of Monosaccharides
Glucose in common with other hexoses and pentoses easily forms stable ring structure. At any one time most molecules oxists as rings rather than
In case of glucose carbon atom number 1 may combine with the oxygen atom an carbon 5. This form a six -sided structure known as a pyranose ring
In case of fructose, carbon atom number 2 links with the oxygen an carbon atom number. This form a five sided structure known as furanose ring Both glucose and fructose can exist in beth pyranose ring.
In case of fructose, carbon atom number 2 links with the oxygen on number 5. This form a five sides structure known as furanose ring Both glucose and fructose can exist in both pyranose and furanose and furanose ring form.
STRUCTURE PG 13 UB
Furanose
o Most carbohydrate in common glucose can exists as a numbee of isomers (they posses the same molecular formula but differ in the arrangement of this atoms).
one type of isomer called stereo isomerism. occurs when the atom, or group, are joined together but differ in Their arrangement in space one form of stereoisomer is called Optical Isomersm, result in isomer which can rotate the plane of polarized light.
If the substance rotates the plane of polarisation to the right it is said to be dexTro-rotatory (d) and if to the left is laevo-rotatory (L) Optical isomerism is a property of any compound which can exist in two forms whose structure are minor image. Like right and left handed gloves
Example.
Stady the structure of glycerin (ghycer aldehyde)
L-Form isomer mirror. D-form isomer
Functions of monosaccharides.
1. PENTOSES (C5H10O5 ) e.g. ribose, deoxyribose, ribulose.
HEXOSES (C6H12O6) e.g. fructose, glucose, galactose.
TRIOSES (C3H6O3) e.g. glyceraldehydes, dihydroxyacetone.
Disaccharides
*Disaccharides are formed by the condensation or polymerlization of two monosaccharides.
The most common disaccharides are;
In reducing sugars e.g. Lactose and maltose, one of the hexose residue retains its aldehyde or ketone groups as an intact unit as reducing sugar.
Maltose is a disaccharide produced upon incomplete hydrolysis of the polysaccharide starch.
-It is found in germinating seeds.
-It is also produced commercially for use in production of beer.
-Maltose is produced of two D-glucose units joined by a α-glycosidic bond between the anomeric carbon of one glucose unit and the number 4 carbon of the other glucose unit.
This specific bond formed an α-1,4-glycosidic bond also found in starch and glycogen.
NB: The numeric hydroxyl group of one of the glucose units participates in the glycosidic bond and
Therefore cannot be easily oxidized.
However the anumeric hydroxyl of the other glucose unit is not as occupied and this glucose unit exists in the equilibrium with free aldehyde solution.
Thus maltose is oxidized by Fehling‟s solution, benedict‟s solution or any other suitable reagent.
Lactose
Constitutes some 3% to 5% of the milk of animal including cows and humans.
This disaccharide is composed of one galactose unit and one glucose unit joined by a glycosidic bond between the anomer of galactose and the number 4 carbon of glucose. A β-1, 4 –glycosidic bond.
Glucose unit of the lactose still exists as an equilibrium mixture of α and β anomers and the free aldehyde in solution. Lactose is thus a reducing sugar.
Sucrose
-It is found in fruits and vegetables.
-Sugarcane and sugar beets are the commercial sources and used as table sugar.
-Sucrose is composed of one fructose unit joined by two glycosidic bonds.
Sucrose is not a reducing sugar since both anomeric carbons participates in the glycosidic bonds and thus no free aldehyde or ketone exists in solution.
NB: D is the hydroxyl group attached to the anomeric carbon atom (the anomeric hydroxyl group) is
drawn on the same side of the ring as the last -CH2OH group for the β-anomer and the opposite side of the ring for the α-anomer.
The D-galactose only differs from the D-glucose only in the orientation of the groups bonded to
Carbon no. 4. Ingested D-glucose (from milk and some other complex polysaccharide) is normally converted to D glucose in the human body.
The inability to perform this ionization (conversion of one isomer to another) results in a disease called galactosemis.
POLYSACCHARIDES
-Have high molecular weight formed by condensation of large number of monosaccharide units.
They include;
Starch, glycogen, cellulose, chitin and insulin.
-All polysaccharides are insoluble in water forming colloidal solution.
-They are non –reducing sugars.
-They are Non- crystalline and as structural materials e.g. Cellulose.
-Represented by chemical formula ( C5H10O5) n or (C6H10O5)n where n is a whole number ranging from 300-400.
1. Starch
It forms a solution with hot water and a gel on cooling.
During digestion, it is converted to a mixture of detrins. Later from maltose to glucose units.
It is largely stored in plants and it is a result of photosynthesis.
In plants, starch is found in the storage parts such as roots and stem tubers, corn and some rhizomes.
A starch granule is composed of
A core of amylase
Amylopeptin
Amyloplast membrane.
Diagrams of amylase and amylopectin.
NB: Amylase and amylopectin are two different forms of starch.
Amylase is linear polymer of α-1, 4-glucose unit and is insoluble in water.
Amylopectin is a branched polymer; the main chain of amylopectin is joined by α-1,4-glycosidic bond as in amylase. However about every 20-30 glucose units there are branches joined by α1,6-glycosidic bond.
Amylopectin is not soluble in water.
When boiled to about 200C starch is partially hydrolyzed to a mixture of dextrins. However, when heated with dilute mineral acids, starch is hydrolyzed via dextrin to glucose.
-In living things (tissues) the hydrolysis is of the following sequence.
-A suspension of glucose gives a blue black coloration with iodine.
-Amylopectin is compact as it has many branches of 1, 6- glycosidic bonds.
Biological importance
GLYCOGEN
-This is called animal starch formed by condensation polymerization of glucose on units.
-It is very similar to amylopectin in structure.
-It is a polymer of glucose units joined by α-1,4- bonds and with α-1,6- bonded branches . it is a white soluble powder and non reducing sugar.
OCCURRENCE
Glycogen differs from amylopectin because it is more highly branched than amylopectin with one branch point about every 8 and 12 glucose units.
Biological advantage.
It is important food storage in muscle and liver of vertebrates and fungi. It provides energy and is an energy substance.
CELLULOSE
This is an important structural material in plants.
It largely constitutes the chemistry of the cell wall.
-Chemically cellulose is composed of several thousands of glucose units joined together by 1, 4- glycosidic bonds. The units are so arranged that the bonds alternate in appearance.
-This lead to the cross links of hydrogen bonds between the parallel running cellulose molecules.
As a result of this, cellulose becomes tough with very high tensile strength.
The shape of a cellulose fibre is of the nature below.
Chemical structure of cellulose is presented as follows.
Hydrolysis of cellulose.
In the living tissues, hydrolysis of cellulose takes place in two stages;
Commercial use of cellulose
It is a raw material in the manufacture of many industrial products such as papers, rayon and plastics.
The rayon made from cellulose are used in the manufacture of industrial belts and tyre cords.
Cellulose derivatives such as cellulose nitrate are used in the manufacture of films.
Cotton, a pure form of cellulose is used in the manufacture of clothes.
CHITIN
This is closely related to cellulose in structure and function, being a structural polysaccharide.
-Structurally it is identical to cellulose except that the OH group at carbon 2 is replaced by – NH.CO. NH3.
-This is a result of amino sugar (glucosamine) combine with acetyl group.
Chitin is therefore a polymer of N-acetylglucoamine.
Inulin
This is another storage carbohydrate which largely occurs of many plants.
It also occurs in small quantities in many monocots. Hydrolysis by dilute mineral acids or specific enzymes e.g. inulin produce fructose only.
It is a polymer of fructose molecule.
Inulin inulase fructose
Summary roles of carbohydrates.
They built up a cell plasma membrane. It is made up of carbohydrates and so they are used to build up the body of a living organism.
They are used as a substrate in respiration (to produce energy) as raw materials. Glucose is the base raw material in glycolysis.
Are useful in pollination. Nectar which attracts pollinators is made up of sugars.
Are useful in storage purpose for future metabolism eg starch, glycogen and laminarin.
Used in the balance of osmotic pressure as they make solutes in the blood.
*Other uses are from the above discussions.
LIPIDS
These are organic compound made up of elements carbon, hydrogen and oxygen in which its proportion of oxygen is smaller than that of hydrogen (i.e. not in the ratio of carbon dioxide of 2:1)
Properties of lipids.
The features that characterize the lipids include the following;
They are either liquids or non-crystalline solids at room temperatures.
They are higher than water ( less dense than water)
They are hydrolyzed by alkaline into their respective constituent compounds. This process is called saponification.
They contain either saturated or unsaturated hydrocarbon chains.
In the presence of water and alcohol they form an emulsion.
*They are esters of higher aliphatic alcohols.
*all lipids are insoluble in water but soluble in organic compounds or solvents e.g. ether, chloroform and hot alcohol.
They occur in adipose tissues of animals and some are a component of the protoplasm of all living cells.
Lipids have ester linkage.
I.e.
Because of unsaturated bonds which are easy to break, that are why they are liquid at room temperature, solids contain saturated bonds.
SIMPLE LIPIDS
Simple lipids are oils and fats of which are esters of glycerol. (Higher alcohol). Than glycerol forms the ester called waxes.
-Oils and fats are formed by the combination of fatty acids and glycerol e.g. oleic acid which are widely distributed in many fats and oils.
-They are also known as triglycerides.
Natural fats and oils.
They are a mixture of glycerides (esters) of fatty acids and glycerol.
Oils: contain greater proportion of unsaturated fatty acids; they are liquid at 20C.
Fats: contain a greater proportion of saturated fatty acids; they are solids at 20C.
BIOLOGICAL IMPORTANCE OF LIPIDS.
They form an insulation material thus prevent heat loss in organisms and animals particularly.
Prevent water loss, form water proof in organisms, plants and insects.
Can be a stored form of energy in the body of an organism e.g. amoeba and seed like units.
Form the basic constituent of the cell membrane as well as the cell components.eg phospholipids
Enables large aquatic organisms like whales to have buoyancy.
Contains basic fat soluble vitamins A, B, D and K.
Forms the natural rubber.
It is a constituent of hormones like steroids e.g. oestrogen, progesterone, also acdysome hormone in insects and crustacea are made up of lipids.
Gives more energy in metabolism.
Used to make bile salts (sodium taurochlorate and sodium glycochorate) for emulsification in the duodenum.
Limits the linkage of small molecules across plasma membrane (cholesterol).
Constituent of myelin sheath; helps to prevent outward flow of ions which would short circuit the movement of ions along the nerve. Also enhance the salutatory condition.
PROTEINS
Proteins are nitrogenous compounds formed by condensation polymerization of larger number of amino acids.
-Proteins are thus polymer molecules of amino acids.
Element present in proteins are carbon, hydrogen, oxygen, nitrogen, sulphur acid and phosphorous and iron.
THE AMINO ACIDS
There are 20 amino acids which are polymerized to give many types of proteins.
Physical properties.
Substances which are protein in nature are;
GENERAL PROPERTIES OF PROTEINS
Many are large dimmers with many amino acid units. Eg serum globulin of human blood have 736 amino acids, myosin of muscle has 780 amino acids.
-In solid state the amino acid have base salt like properties because they have both a positive charge part and a negative charge part such substances are called zwitterions.
-Zwitterions are produced from the molecular form of the amino acid by internal-acid base reaction.
NOTE: in the reaction above, neither the molecular form nor the zwitterions form has a net electrical charge. In aqueous solution these two forms are in equilibrium but the equilibrium overwhelmingly favors the zwitterions at any pH.
At any pH, some of the alamine in solution exists in the positive ion form. Some of it in the negative ion form, some in the zwitterions form and some in molecular form.
In solution that are predominantly basic (i.e. pH btn 8.5 to 10.5), no single form of alanine predominates. In this pH range, there are roughly comparable amount of zwitterions and the negative charged.
At higher pH protein and amino acid become more negative while at low pH they become more positively charged.
Properties of isoelectric point.
Structure of amino acids.
The amino acid consists of an α carbon surrounded by;
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