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CHAPTER - BIOMOLECULES CARBOHYDRATES The large polymeric or monomeric molecules of polyhydroxy aldehydes or ketones are called carbohydrates. Carbohydrates have the following functions in the living organisms: (i) Carbohydrates support plant structure. (ii) Carbohydrates store chemical energy in plants (in the form of sugars and starch). (iii) Carbohydrates act as the major source of energy for animals and human beings. (iv)Carbohydrates act as energy storage in the form of glycogen in animal body.

Classification of carbohydrates: a) According to hydrolysis: i. Monosaccharides: These are simplest carbohydrates which cannot be hydrolysed into simpler compounds. E.g. Glucose, mannose, fructose and galactose. ii. Oligosaccharides: Carbohydrates which give 2 to 10 monosaccharide units on hydrolysis. E.g. Sucrose, Lactose, Maltose. iii. Polysaccharides: Carbohydrates which on hydrolysis give large number of monosaccharide units. E.g. Cellulose, starch. b) According to reducing nature: i.Reducing sugars: These are the carbohydrates which can reduce Tollens reagent and Fehlings solution. E.g.Glucose, mannose,fructose (mainly monosaccharides). ii.Non reducing sugars: These are the carbohydrates which cannot reduce Tollens reagent and Fehlings solution. E.g. Sucrose, Lactose, Maltose, Cellulose, starch (mainly oligosaccharides and polysaccharides).

Description of monosaccharide (glucose) Glucose Glucose is an polyhydroxy aldohexose. It occurs in ripe grapes, honey, and most of the sweet fruits. It is also known as grape sugar or dextrose. It melts at 146C. It gives reactions of aldehydes and alcohols. Structure of glucose (C6H12O6): a)open chain structure:
H C = O I H C OH I HO C H I H C OH I H C OH I CH2OH

C HO H OH H H OH H OH OH C H 2O H

b)closed/ring structure: Structure of glucose is not linear or as shown by Fischer projection it has a ring structure between C1 & C5.

This open chain formula of glucose explains most of the reactions given by glucose but fails to explain the D Glucose following facts: (i) Although it contains an aldehyde group, but it does not react with NH3 , Schiffs reagent, 2,4 DNP and NaHSO3. (ii) There are two forms of glucose: -glucose and -glucose. - and - forms show specific rotation of + 110 and + 19.7 respectively. (iii) In aqueous solution, both the forms of glucose show mutarotation. -form undergoes mutarotation from 110 to 52.5, while -form shows a mutarotation from 19.7 to 52.5. (iv) Pentaacetyl glucose does not react with hydroxyl amine. These observations shows the absence of free CHO group in Glucose.

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Chemical evidence of ring structure of glucose: a)It does not react with Schiffs reagent, NaHSO3 and 2, 4 DNP though glucose contain aldehydic group as these compounds are weak reagents. Thus, could not able to break the ring to give the aldehyde test. This confirms aldehyde is in combined state. Glucose can give test with Tollens reagent and fehling solution as these are moderate reagent and break the ring due to which CHO group become free to react. Anomers: Such pairs of optical isomers which differ in configuration only around C1 atom are called anomers. E.g: -D-glucose and -D-glucose. Glucose exists in two different crystalline forms i.e. -D-glucose and -D-glucose. b)Penta acetate of glucose doesnt react with Hydroxylamine as CHO group is not free and exist in combined form.

-D-glucose It is obtained by crystallization from concentration solution of glucose. It has m.p of 419 K. -D-glucose It is obtained by crystallization from hot & saturated aqueous solution at 371 K. Its m. p is 423 K.

Mutarotation: The spontaneous change in specific rotation of an optically active compound is called mutarotation. E.g. D-glucose with specific rotation []D = +110 and -D-glucose with specific rotation []D =+19.7 When both form is dissolved in water & allowed to stand, the specific rotation of the solution changes slowly and reaches a constant value of +52.5. -D-glucose open chain form -D-glucose sp. rot = +19.7 sp. rot = +110 sp. rot = +52.5 Preparation of glucose:

a)From acidic hydrolysis of sucrose: b) From acidic hydrolysis of starch:

C12H22O11 + H2O sucrose

Structure elucidation of glucose: a) Presence of six carbon atoms linked in straight line:

(C6H10O5)n + H2O starch

C6H12O6 + C6H12O6 glucose fructose n C6H12O6 glucose

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b) Presence of carbonyl (>C=O) group: i)with HCN:

ii)with NH2OH:

c) Presence of aldehyde (-CHO) group: COOH | (CHOH)4 CHO get oxidized into COOH group by mild | oxidizing agent Br2 water. CH2OH Gluconic acid d) Presence of one primary alcohol group ( CH2OH): COOH | (CHOH)4 oxidation of CH2OH into COOH shows presence of 10 alc. | COOH Saccharic acid e) Presence of five OH (hydroxyl gp): CHO |
Acetic anhydride

(CHOCOCH3)4 OH is converted to OCOCH3 | CH2OCOCH3 Glucose penta acetate

FRUCTOSE It is a polyhydroxyketohexose. It is found in fruits and honey. It melts with slight decomposition at 102C. It is twice as sweet as ordinary sugar. Structure of fructose. Fructose has a molecular formula C6H12O6, and has a keto group in it. Fischer open chain structure closed/ring structure

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1. 2. 3.

Glucose

Difference between structures of Glucose & Fructose

Aldose sugar

Aldehyde group at C1.

Fructose

DISACCHARIDES: The carbohydrates which can produce two monohydric units on Hydrolysis. Glycosidic linkage: In disaccharides two monosaccharides are joined by an oxide linkage formed by the loss of H2O molecule. Such linkage through O atom is called as glycosidic linkage. Hydolysis Ex. Sucrose Glucose + Fructose a) Sucrose: It is a disaccharide made up of -D-glucose and -D-Fructose. Glycosidic linkage in sucrose is in between C1 of -D-glucose & C2 of -D-Fructose.

Ring is between C1 & C5 i.e. 5 membered carbon ring.

Ketose sugar

Ketone group at C2.

Ring is between C2 & C5 i.e. 4 membered carbon ring.

Invert Sugar - Canesugar (sucrose) is dextrorotatory has specific rotation of a + 66.5. On hydrolysis,it gives dextrorotatory glucose and laevorotatory fructose. The resulting solution which contains equimolar amounts of glucose and fructose is laevorotatory with specific rotation of 39.7. Thus, the sign of rotation changes after hydrolysis. That is why, hydrolysis of canesugar is commonly called inversion of sugar. The equimolar mixture of glucose and fructose is called invert sugar. Sucrose
2
o
nH O

[ ]D = +62.4

[ ]D = +52.5

Glucose

[ ]D = 92.4o

Fructose

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b) Maltose : It is composed of two -D-glucose units. The glycosidic linkage is between C1 and C4 of two glucose units. On reduction, free CHO group can be obtained at C 1 of second glucose.

c) Lactose (Milk Sugar) It is made up of -D-glucose and -D-galactose. The glycosidic linkage in between C1 of galactose and C4 of glucose.

POLYSACCHARIDES These are the carbohydrates which produce large number of monosaccharide units on Hydrolysis. a) Starch(C6H10O5)n: It is a polymer of -D -glucose and consists of two components: Amylose and Amylopectin. Amylose i)Water soluble component ii)It is a long unbranched chain polymer iii)Contains 200 1000 -D -(+)- glucose units held by glycosidic linkages involving C1 C4 glycosidic linkage iv)Constitutes about 15-20% of starch Amylopectin i)Water insoluble component ii)It is a branched chain polymer iii)It is a branched chain polymer of -D -glucose units in which chain is formed by C1C4 glycosidic linkage whereas branching occurs by C1C6 glycosidic linkage. iv)Constitutes about 80- 85% of starch

b) Cellulose(C6H10O5)n: It is a straight chain polysaccharides made of -D-glucose. Glycosidic linkage is between C1 & C4. It is mostly found in plants (cell walls). Cotton is an example of almost pure cellulose, (9095% cellulose). Human digestive system cannot digest cellulose, because it does not have the enzyme which can hydrolyse cellulose. c) Glycogen: It is a branched polymer of -glucose resembles amylopectin in its structure. It is found in all animal cells, mainly in the liver, muscles and brain. Glycogen acts as a short-term food reserve in animals as it breaks down in glucose.

Glucose and sucrose are soluble organic compounds as they contain number of OH groups which forms inter H bonds with H2O molecules while organic compounds like benzene and cyclohexane are insoluble in water due to absence of polar group like OH.

PROTEINS Amino Acids: these are the organic compounds containing carboxylic acid (COOH) and amino ( NH2) group. Only amino acids are obtained on hydrolysis of proteins.

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Classification of Amino Acids a) On the basis of number of NH2 & -COOH groups i)Acidic amino acids: Number of -COOH groups > Number of -NH2 groups ii) Basic amino acids: Number of -NH2 groups > Number of -COOH groups iii)Neutral Amino acids: Number of -COOH groups = Number of -NH2 groups b) According to their synthesis i)Non essential amino acids These are the amino acids which can be synthesised in the body. Ex. Glycine, Alanine,Tyrosine etc. ii)Essential amino acids These are the amino acids which cannot be synthesised in the body. Ex. Leucine, Lysine, Phenylalanine, Valine etc.

Physical Properties of Amino acids: a) Colourless, crystalline solids, water, soluble & have high melting point. b) They behave the salts (amphoteric). It is due to the presence of both acidic (carboxylic group) and basic (amino group) in the same molecule. c) In aqueous state amino acids exists as dipolar as known as Zwitter ion.

Zwitter ion - Amino acids contain both an acidic carboxylic ( COOH) group, and a basic amino ( NH2) group in the same molecule. In aqueous solutions, the COOH group loses a proton to form carboxylate ( COO ) ion, and the amino ( NH2) group gains one proton to form NH3 + . Thus, in aqueous solution, amino and carboxyl groups are in the ionized form, and the amino acid molecule exists as a dipolar ion. Such a dipolar ion of an amino acid is called zwitter ion.

(a) Reaction of amino acids with an acid:

(b) Reaction of amino acids with a base:

Isoelectronic point: The pH at which the dipolar Zwitter ion exists as neutral ion and does not migrate to either electrode cathode or anode is called isoelectronic point. Proteins: Proteins are the polymers of -amino acids and they are connected to each other by peptide bond or peptide linkage. A polypeptide with more than hundred amino acid residues, having molecular mass higher than 10,000u is called a protein.

Peptide linkage: Peptide linkage is an amide linkage formed by condensation reaction between COOH group of one amino acid and NH2 group of another amino acid.

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Dipeptide - The peptide formed due to the condensation of only two molecules of the same or different amino acids is called a dipeptide.

Tripeptide - The peptide formed due to the condensation of only three molecules of the same or different amino acids is called a tripeptide.

Structures of Protein - All proteins contain amino acids. These amino acids are linked to each other by peptide bonds. The structure of proteins can be described mainly in terms of three levels of structural organization. a) Primary Structure of Proteins: The linear sequence in which amino acids are arranged in a protein is called its primary structure.

The amino acid sequence in a protein determines its function and is critical to its biological activity. Even a change of just one amino acid can drastically alter the properties of the entire protein molecule. EX: Normal haemoglobin: Val His Leu Thr Pro Glu Glu Lys Sickle-cell haemoglobin: Val His Leu Thr Pro Val Glu Lys b) Secondary Structure of Proteins: It refers to the shape in which long polypeptide chain can exist. Two different types of structures: i) -Helix structure. This type of structure becomes possible when the Rgroups of the amino acids are quite large. The polypeptide chain coils up to form spiral structure, and the turns of the coil are held together by N H...... O = C hydrogen bonds. Each NH group is hydrogen bonded to the oxygen of the carboxyl group of the third amino acid.

Also known as 3.613 helix since each turn of the helix has approximately 3.6 amino acids and a 13 membered ring is formed by H bonding. C = O and N H group of the peptide bonds are trans to each other. Many fibrous proteins such as -keratin in hair, nails, wool, skin and myosin in muscles have -helix structure. Stretching property of human hair is due to the helical structure of -keratin in hair.

ii) -Flat sheet and -pleated sheet structures. The flat sheet structure becomes possible in proteins containing amino acids with small R-group. In this structure, the long polypeptide chains lie side by side in a zig-zag manner with alternate R-group on the same side. Each polypeptide chain is held to the two adjacent chains (one on each side) by intermolecular hydrogen bonds. This arrangement leads to a flat sheet structure. The silk protein fibroin has -pleated sheet structure. It is due to the pleated structure that silk fibre cannot be stretched. However, it can be bent or folded easily. iii) Tertiary structure of proteins: It represents the overall folding of the polypeptide chain i.e., further folding of the 2 structure. Types of bonding which stablise the 3 structure i)Disulphide bridge (-S S-) ii)H bonding (C = O H N) iii)Salt bridge (COO +NH3) iv)Hydrophobic interactions v)van der Waals forces Two shapes are possible: Fibrous proteins Globular proteins When the polypeptide chains run parallel and This structure results when the chains of are held together by hydrogen and disulphide polypeptides coil around to give a spherical bonds, then fibre like structure is formed. shape. Such proteins are generally insoluble in water These are usually soluble in water. Examples: keratin (present in hair, wool, silk) Examples: Insulin and albumins and myosin (present in muscles), etc

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iii) Quaternary structure of proteins: Some of the proteins are composed of two or more polypeptide chains referred to as sub-units. The spatial arrangement of these subunits with respect to each other is known as quaternary structure of proteins. Denaturation of Proteins The process which leads to the changes in the physical and biological properties of proteins without affecting its chemical composition is called denaturation of protein. Example: coagulation of egg white on boiling, curdling of milk. Denaturation is caused by the following factors: (a) Change in the pH. (b) Increase in temperature. (c) Presence of acids, alkalies and/or salts. (d) Exposure to ultraviolet rays and X-rays. Denaturation causes changes only in the secondary and tertiary structures of proteins. The primary structure of any protein does not change due to denaturation. When the egg is boiled, the protein first undergo denaturation and then coagulation, and the water present in the egg gets absorbed/adsorbed in the coagulated proteins mainly through H-bonding. Vitamins: Vitamins are organic compounds required in the diet in small amounts to perform specific biological functions for normal maintenance of optimum growth and health of the organism. Classification of vitamins: Vitamins are classified into two groups depending upon their solubility in water or fat. Fat soluble vitamins These vitamins are soluble in fat and oils but insoluble in water. They are stored in liver and adipose (fat storing) tissues Example: Vitamin A, D, E and K Name of vitamin Vitamin A Vitamin B1 (Thiamine) Vitamin B2 (Riboflavin) Water soluble vitamins These vitamins are soluble in water.

Important vitamins, their sources and their deficiency diseases: Source Fish liver oil, carrots, butter and milk Yeast, milk, green vegetables and cereals Milk, egg white, liver, kidney

Water soluble vitamins must be supplied regularly in diet because they are readily excreted in urine and cannot be stored (except vitamin B12) in our body. Example: Vitamin C, B group vitamins Deficiency diseases Xe r o p h t h a l m i a (hardening of cornea of eye) Night blindness Beri beri (loss of appetite, retarded growth) Cheilosis (fissuring at corners of mouth and lips), digestive disorders and burning sensation of the skin. Convulsions Pernicious anaemia (RBC deficient in haemoglobin) Scurvy (bleeding gums)

Vitamin B6 (Pyridoxine) Vitamin B12 Vitamin C (Ascorbic acid) Vitamin D Vitamin E Vitamin K

Yeast, milk, egg yolk, cereals and grams Meat, fish, egg and curd Citrus fruits, amla and green leafy vegetables Exposure to sunlight, fish and egg yolk

Vegetable oils like wheat germ oil, sunflower oil, Green leafy vegetables

Rickets (bone deformities in children) and osteomalacia (soft bones and joint pain in adults) Increased fragility of RBCs and muscular weakness Increased blood clotting time

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Nucleic Acids These are the particles present in the nucleus & responsible for heredity information and mainly made up of Biomolecules. Constituents of Nucleic acids-Nucleic acids contain the following three constituents. i) a pentose sugar (ribose or deoxyribose), ii)a nitrogen containing heterocyclic base: a purine or a pyrimidine base, iii)a phosphate group. Nucleosides These are the Biomolecules which are composed of a pentose sugar and nitrogenous base.

Nucleotide These are the Biomolecules which are composed of a pentose sugar, nitrogenous base and phosphate group.

Phospodiester linkage- Nucleotides are joined together by 5 & 3 carbon atoms of pentose sugar. This linkage is known as phospodiester linkage.

There are two types of nucleic acids: Deoxyribonucleic acid (DNA) and Ribonucleic acid (RNA) RNA S.No. DNA 1 DNA is deoxyribonucleic acid. RNA is ribonucleic acid. 2 DNA is mainly found in the chromosomes (in the nucleus RNA occurs mainly in the cytoplasm, but it is also of the cell). found in the nucleolus, nucleoplasm and chromosomes. 3 4 5 DNA has double-stranded helix and both the helical strands are coiled in opposite directions. DNA nucleotides consist of deoxyribose sugar. Pentose Sugar known as -2-Deoxyribose.

RNA is formed of a single strand. RNA molecule may be coiled on itself. RNA nucleotides consist of ribose sugar. Pentose sugar is known as -2-Ribose

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6 7 8 9 The nitrogenous bases found in DNA are: Purine bases: Adenine and Guanine. Pyrimidine bases: Cytosine and Thymine. DNA is the genetic material. The nitrogenous bases found in RNA are: Purine bases: Adenine and Guanine. Pyrimidine bases: Cytosine and Uracil. RNA is not the genetic material.

DNA inter H - bonding between nitrogenous bases: i) A = T / T = A (double inter H-bonded) ii) G C / C G (triple inter H-bonded) DNA on hydrolysis gives equal moles of Guanine to that of Cytosine and of Adenine to that of Thymine therefore DNA is double stranded.

RNA inter H - bonding between nitrogenous bases: i) A = U / U = A (double inter H-bonded) ii) G C / C G (triple inter H-bonded) RNA on hydrolysis does not give equal moles of nitrogenous bases as it single stranded.

RNA is of three types and each type performs different function: i)Messenger RNA: Messenger RNA (m -RNA) is a short-lived molecule that carries genetic information from DNA to the ribosomes where protein synthesis occurs. ii)Ribosomal RNA: Ribosomal RNA (r -RNA) is an integral part of ribosomes that also takes part in protein synthesis. About 75% of the cellular component of RNA is r -RNA. iii)Transfer RNA. Transfer RNA (t -RNA) acts as a carrier of amino acids. The hydrophobic interactions are a major stabilizing force in the tertiary structure of t -RNA.

The two strands of DNA are not identical but are complementary to each other because the hydrogen bonds are formed between specific pairs of nitrogeneous bases. Adenine forms hydrogen bonds with thymine whereas cytosine forms hydrogen bonds with guanine.