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UNIT 1: BIOCHEMISTRY
Sample Material on Carbohydrates Includes Material + Previous CSIR Questions on Carbohydrates (2001 -2011) + MCQ for Practice
[Helps in what dept we have to read on Carbohydrates]
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B. Composition, Structure and Function of Biomolecules (Carbohydrates, Lipids, Proteins, Nucleic Acids and Vitamins).
CARBOHYDRATES
he most abundant biomolecules on Earth. Carbohydrates are polyhydroxy aldehydes or ketones with the empirical formula (CH2O)n (few contain N, P and S).
Classification Carbohydrates are classified into four major classes 1. Monosaccharides 2. Disaccharides 3. Oligosaccharides and 4. Polysaccharides
Monosaccharides
Monosaccharides are colorless, crystalline solids that are freely soluble in water.
The backbones are unbranched carbon chains with all carbon atoms are linked by single bonds (In the open-chain form, one of the carbon atoms is double-bonded to an oxygen atom to form a carbonyl group) The monosaccharide, aldose with carbonyl group is an aldehyde group and ketone group for the monosaccharide is a ketose. The simplest monosaccharides are the two 3-carbon trioses: glyceraldehyde (aldotriose), and dihydroxyacetone (ketotriose). The tetroses, pentoses, hexoses, and heptoses are monosaccharides with 4, 5, 6, and 7 carbon atoms, respectively, in their backbones and are named as aldotetroses and ketotetroses, aldopentoses and ketopentoses, and so on. The hexoses, which include the aldohexose, D-glucose and the ketohexose D-fructose, are the most common monosaccharides in nature. The aldopentoses D-ribose and 2-deoxy-D-ribose are components of nucleotides and nucleic acids. Except dihydroxyacetone, all the monosaccharides contain one or more asymmetric (chiral) carbon atoms and thus occur in optically active isomeric forms.
The simplest aldose, glyceraldehyde, contains 1 chiral center and has 2 different optical isomers, or enantiomers. In general, a molecule with n chiral centers can have 2n stereoisomers. Glyceraldehyde has 21 = 2; the aldohexoses, with four chiral centers, have 24 = 16 stereoisomers. The stereoisomers of monosaccharides divided into two groups that differ in the configuration about the chiral center most distant from the carbonyl carbon. Those in which the configuration at this reference carbon is the same as that of D-glyceraldehyde are designated D isomers, and those with the same configuration as L-glyceraldehyde are L isomers. When the hydroxyl group on the reference carbon is on the right in the projection formula, the sugar is the D isomer; when on the left, it is the L isomer. Of the 16 possible aldohexoses, eight are D forms and eight are L. Most of the hexoses of living organisms are D isomers (exception L-arabinose). Two sugars that differ only in the configuration around one carbon atom are called epimers; D-glucose and D-mannose, which differ only in the stereochemistry at C-2, are epimers, as are D-glucose and Dgalactose (which differ at C-4). In aqueous solution, aldotetroses and all monosaccharides with five or more carbon atoms occur predominantly as cyclic (ring) structures in which the carbonyl group forms a covalent bond with the oxygen of a hydroxyl group along the chain. The general reaction between alcohols and aldehydes or ketones to form derivatives called hemiacetals or hemiketals, results in an extra asymmetric carbon atom and thus can exist in two stereoisomeric forms. D-glucose exists in solution as an intramolecular hemiacetal in which the free hydroxyl group at C-5 has reacted with the aldehydic C-1, rendering a carbon asymmetric and producing two stereoisomers, designated and . These six-membered ring compounds are called pyranoses because they resemble the six membered ring compound pyran. The systematic names for the two ring forms of D-glucose are -D-glucopyranose and -Dglucopyranose. Aldohexoses also exist in cyclic forms having fivemembered rings, which, because they resemble the fivemembered ring compound furan, are called furanoses. The six-membered aldopyranose ring is more stable than the aldofuranose ring and predominates in aldohexose solutions. The monosaccharide isomers that differ only in their configuration about the hemiacetal or hemiketal carbon atom are known as anomers and the hemiacetal carbon atom is called the anomeric carbon.
The mutarotation is process, where both and anomers of D-glucose interconvert in aqueous solution. Thus, a solution of -D-glucose and a solution of -D-glucose eventually form identical equilibrium mixtures having identical optical properties. This mixture consists of about 1/3 -D-glucose, 2/3 -D-glucose, and very small amounts of the linear and five-membered ring (glucofuranose) forms. In ketohexoses, the hydroxyl group at C-5 (or C-6) reacts with the keto group at C-2, forming a furanose (or pyranose) ring containing a hemiketal linkage. The more common anomer of Fructose is -Dfructofuranose. Haworth perspective formulas are commonly used to show the stereochemistry of ring forms of monosaccharides. They are a number of sugar derivatives in which -OH group in the parent compound is replaced with another substituent, or a carbon atom is oxidized to a carboxyl group. In glucosamine, galactosamine, and mannosamine, the hydroxyl at C-2 of the parent compound is replaced with an amino group. In N-acetylglucosamine, the amino group is condensed with acetic acid. Bacterial cell walls contain a derivative of glucosamine, N-acetylmuramic acid, in which lactic acid (a threecarbon carboxylic acid) is ether-linked to the oxygen at C-3 of N-acetylglucosamine. The substitution of hydrogen for the -OH group of L-galactose or L-mannose at C-6 produces L-fucose or Lrhamnose, respectively; these deoxy sugars are found in plant polysaccharides and in the complex oligosaccharide components of glycoproteins and glycolipids. Oxidation of the carbonyl (aldehyde) carbon of glucose to the carboxyl level produces gluconic acid; other aldoses yield other aldonic acids. Oxidation of C-6 of glucose, galactose, or mannoseforms the corresponding uronic acid: glucuronic, galacturonic, or mannuronic acid. Both aldonic and uronic acids form stable intramolecular esters called lactones. N-acetylneuraminic acid (sialic acid), a derivative of N-acetylmannosamine, is a component of many glycoproteins and glycolipids in animals.
Monosaccharides as Reducing Agents
Monosaccharides can be oxidized by relatively mild oxidizing agents such as ferric (Fe3+) or cupric (Cu2+) ion and carbonyl carbon is oxidized to a carboxyl group. Glucose and other sugars capable of reducing ferric or cupric ion are called reducing sugars. This property is the basis of Fehlings reaction, a qualitative test for the presence of reducing sugar. For many years this test was used to detect and measure elevated glucose levels in blood and urine in the diagnosis of diabetes mellitus. Now, more sensitive methods for measuring blood glucose employ glucose oxidase.
Disaccharides
Disaccharides (such as maltose, lactose, and sucrose) consist of two monosaccharides joined covalently by an O-glycosidic bond. This reaction represents the formation of an acetal from a hemiacetal and an alcohol (-OH of the second sugar molecule). Glycosidic bonds are readily hydrolyzed by acid but resist cleavage by base. The oxidation of a sugars anomeric carbon by cupric or ferric ion (the reaction that defines a reducing sugar) occurs only with the linear form, which exists in equilibrium with the cyclic form(s). When the anomeric carbon is involved in a glycosidic bond, that sugar residue cannot take the linear form and therefore becomes a nonreducing sugar. In describing disaccharides or polysaccharides, the end of a chain with a free anomeric carbon (one not involved in a glycosidic bond) is commonly called the reducing end. The maltose, a disaccharide contains two D-glucose residues joined by a glycosidic bond between C-1 (the anomeric carbon) of one glucose residue and C-4 of the other.
Since, maltose retains a free anomeric carbon (C-1 of the glucose residue on the right), maltose is a reducing sugar. The configuration of the anomeric carbon atom in the glycosidic linkage is . The glucose residue with the free anomeric carbon is capable of existing in - and -pyranose forms. The lactose, a disaccharide occurs naturally only in milk, yields D-galactose and D-glucose on acid hydrolysis. The anomeric carbon of the glucose residue is available for oxidation, and thus lactose is a reducing disaccharide. Sucrose is a disaccharide of glucose and fructose. In contrast to maltose and lactose, sucrose contains no free anomeric carbon atom; the anomeric carbons of both monosaccharide units are involved in the glycosidic bond. Sucrose is therefore a nonreducing sugar. Nonreducing disaccharides are named as glycosides.
Trehalose, a disaccharide of D-glucose that, like sucrose, is a nonreducing sugaris a major constituent of the circulating fluid (hemolymph) of insects, serving as an energy-storage compound.
Polysaccharides
Most carbohydrates found in nature occur as polysaccharides (also called glycans). Homopolysaccharides contain only a single type of monomer; heteropolysaccharides contain two or more different kinds.
Unlike proteins, polysaccharides generally do not have definite molecular weights. The proteins are synthesized on a template (messenger RNA) of defined sequence and length, by enzymes that follow the template exactly. For polysaccharide synthesis there is no template; rather, the program for polysaccharide synthesis is intrinsic to the enzymes that catalyze the polymerization of the monomeric units, and there is no specific stopping point in the synthetic process. The most important storage polysaccharides are starch in plant cells and glycogen in animal cells. Starch and glycogen molecules are heavily hydrated, because they have many exposed hydroxyl groups available to hydrogen-bond with water.
Starch
Contain two types of glucose polymers, amylase and amylopectin. Amylose consists of long, unbranched chains of D-glucose residues connected by (14) linkages. Amylopectin also has a high molecular weight (up to 100 million) but unlike amylose is highly branched. The glycosidic linkages joining successive glucose residues in amylopectin chains are (14); the branch points (occurring every 24 to 30 residues) are (16) linkages.
Glycogen
Like amylopectin, glycogen is a polymer of (14)-linked subunits of glucose, with (16)-linked branches, but glycogen is more extensively branched (on average, every 8 to 12 residues) and more compact than starch. Each branch in glycogen ends with a nonreducing sugar unit, a glycogen molecule has as many nonreducing ends as it has branches, but only one reducing end. Why not store as D-glucose instead Glycogen? The hepatocytes that store glycogen equivalent to a glucose concentration of 0.4 M, which is insoluble and contributes little to the osmolarity of the cytosol (0.01 M). If the cytosol contained 0.4 M glucose, the osmolarity would be elevated, leading to osmotic entry of water that might rupture the cell.
Dextrans
Made up of ( 16)-linked poly-D-glucose; all have (13) branches, and some have (12) or (14) branches. Dental plaque (formed by bacteria growing on the surface of teeth) is rich in dextrans. Synthetic dextran, Sephadex used in size-exclusion chromatography.
Cellulose
Like amylase, it is a linear, unbranched homopolysaccharide, consisting of 10,000 to 15,000 D-glucose units. In cellulose, the glucose residues have the configuration. The glucose residues in cellulose are linked by (14) glycosidic bonds -amylases, enzymes of saliva and intestinal secretions hydrolyze glycogen and starch that break (14) glycosidic bonds between glucose units. Most animals cannot use cellulose, because they lack an enzyme to hydrolyze the (14) linkages. Termites readily digest cellulose, because their intestinal tract harbors a symbiotic microorganism, Trichonympha, that secretes cellulase, which hydrolyzes the (14) linkages. Wood-rot fungi and bacteria also produce cellulase.
Chitin
A linear homopolysaccharide composed of N-acetylglucosamine residues in linkage. Chitin is the principal component of the hard exoskeletons of nearly a million species of arthropods insects, lobsters, and crabs, for example and is the second most abundant polysaccharide, next to cellulose.
Homopolysaccharide Folding
Like Proteins, structures that are stabilized by weak interactions within or between molecules: hydrogenbond, hydrophobic, and van der Waals interactions, and, for polymers with charged subunits, electrostatic interactions. The most stable three-dimensional structure for starch and glycogen is a tightly coiled helix, stabilized by interchain hydrogen bonds with six residues per turn.
Heteropolysaccharides
The rigid component of bacterial cell walls is a heteropolymer of alternating (14)-linked Nacetylglucosamine and N-acetylmuramic acid residues. The linear polymers lie side by side in the cell wall, cross linked by short peptides. The peptide cross-links weld the polysaccharide chains into a strong sheath that envelops the entire cell and prevents cellular swelling and lysis due to the osmotic entry of water. The enzyme lysozyme kills bacteria by hydrolyzing the (14) glycosidic bond between Nacetylglucosamine and Nacetylmuramic acid. The marine red algae have cell walls that contain agar, a mixture of sulfated heteropolysaccharides made up of D-galactose and an L-galactose derivative ether-linked between C-3 and C-6. The two major components of agar are the unbranched polymer agarose (Mr ~120,000) and a branched component, agaropectin.
When agarose in water is heated and cooled, the agarose forms a double helix: two molecules in parallel orientation twist together with a helix repeat of three residues; water molecules are trapped in the central cavity. These structures in turn associate with each other to form a gel a three-dimensional matrix that traps large amounts of water. Agarose gels are widely used as inert supports for the electrophoretic separation of nucleic acids. Agar is also used to form a surface for the growth of bacterial colonies. Glycosaminoglycans Are Heteropolysaccharides of the Extracellular Matrix The extracellular space in the tissues composed of an interlocking meshwork of heteropolysaccharides and fibrous proteins such as collagen, elastin, fibronectin, and laminin. These are heteropolysaccharides of the glycosaminoglycans, are a family of linear polymers composed of repeating disaccharide units. One of the two monosaccharides is either N-acetylglucosamine or N-acetylgalactosamine; the other is in most cases a uronic acid, usually D-glucuronic or L-iduronic acid. The glycosaminoglycan hyaluronic acid contains alternating residues of D-glucuronic acid and Nacetylglucosamine serve as lubricants in the synovial fluid of joints and give the vitreous humor of the vertebrate eye its jellylike consistency. Hyaluronidase, an enzyme secreted by some pathogenic bacteria, can hydrolyze the glycosidic linkages of hyaluronate, rendering tissues more susceptible to bacterial invasion. In many organisms, a similar enzyme in sperm hydrolyzes an outer glycosaminoglycan coat around the ovum, allowing sperm penetration.
Glycoconjugates
Some carbohydrate containing molecules act in cell-cell recognition and adhesion, cell migration during development, blood clotting, the immune response, and wound healing, to name but a few of their many roles. In most of these cases, the informational carbohydrate is covalently joined to a protein or a lipid to form a glycoconjugate, which is the biologically active molecule. Proteoglycans are macromolecules of the cell surface or extracellular matrix in which one or more glycosaminoglycan chains are joined covalently to a membrane protein or a secreted protein. Proteoglycans are major components of connective tissue such as cartilage, in which their many noncovalent interactions with other proteoglycans, proteins, and glycosaminoglycans provide strength and resilience. Glycoproteins have one or several oligosaccharides of varying complexity joined covalently to a protein. They are found on the outer face of the plasma membrane, in the extracellular matrix, and in the blood. Inside cells they are found in specific organelles such as Golgi complexes, secretory granules, and lysosomes. Glycolipids are membrane lipids in which the hydrophilic head groups are oligosaccharides, which, as in glycoproteins, act as specific sites for recognition by carbohydrate- binding proteins.
Extra Name a tetrose Erythrose What is the function of erythorose? It forms a raw material for synthesis of anthocyanin and lignin. What is the other name of fructose? Fruit sugar / Levulose Which sugar is the reserve food of brown algae? Mannitol.(It is an alcohol of the sugar mannose) Glucose is categorized as a monosaccharide. How would you classify cellobiose? Disaccharide.Cellobiose is a disaccharide of Beta-D-Glucose and cannot be digeted by the human gut. Which sugar is found in the germinating starchy seeds? Maltose. Maltose is prepared from starch by hydrolyzing it with the enzyme-----. Diastase. Which mammal among the following has highest lactose content in milk?- Cow, goat, buffalo, human. Answer Human Name a trisaccharide. Raffinose. *It is made of Galactose + Glucose + Fructose In which form is food passed through phloem of plants? Sucrose. What is the food storage polysaccharide in plants? Starch. What is known as 'animal starch'? Glycogen. In which plant is the amount of cellulose the maximum? Cotton. Which compound derived from polysaccharides prevent the coagulation of blood in vessels? Heparin. Name the monomer of chitin? N-Acetyl glucosamine Name a homopolymer of fructose? Inulin. Mostly 25-50 units. Do not confuse with 'insulin'- it is a hormonal protein. The infant brain requires a lot of ----- as a metabolic substrate. Glucose. What are the two fractions of starch? Amylose and Amylopectin. Name two structural Polysaccharides? Chitin and Cellulose.
Previous CSIR Exams Questions on Carbohydrates

1. Milk sugar Lactose, a disaccharide has linkage [CSIR 2003 Dec] a. Glucose + galactose 1 4 b. Glucose + Glucose 1 4 c. Glucose + Fructose 1 6 d. Glucose + Galactose 1 6 2. Sucrose does not occur in its anomeric form while its hydrolyzed product glucose and fructose have anomers. The reason is [CSIR 2007 Jun] a. C1 of glucose and C1 of fructose are bonded in glycosidic linkage b. C1 of glucose and C2 of fructose are bonded in glycosidic linkage c. Sucrose is polysaccharide d. Sucrose is not soluble in water 3. Chitin occurs in cell wall of [CSIR 2008 Dec] a. Bacteria b. Plants c. Fungus d. Mollusc 4. The structure of carbohydrate is shown as below. In polymer the bonding will be [CSIR 2009 Dec]
a. 1,2 b. 1,4 c. 4,6 d. 2,4 5. Starch on treatment with dilute H2SO4 yields free glucose but cellulose does not because [CSIR 2009 Jun] a. Cellulose is linear b. Cellulose is branched c. Starch is carbohydrate d. Starch is linear 6. Area required to store fats in seed as compare to carbohydrate would be [CSIR 2009 Jun] a. Equal b. More c. Less d. Slightly more 7. Maximum possible isomers for glucose are [CSIR 2009 Jun] a. 4 b. 8 c. 16 d. 32 8. Sucrose is composed of [CSIR 2010 Jun] a. Glucose and galactose b. Fructose and galactose c. Glucose and Fructose d. Mannose and fructose 9. Which of the following is a hydrated polymer? [CSIR 2010 Jun] a. Cellulose b. Pectin c. Lignin d. Callose Answers 1a 2b 3c 4b 5a 6c 7c 8c 9a
UNIT 1: BIOCHEMISTRY MCQ for Practice on Carbohydrates

1. Which of these compounds is unable to undergo mutarotation? a. Glucose b. Maltose c. Lactose d. Sucrose 2. Barfoeds is a test for the presence of a. fructose only b. disaccharides c. starch d. monosaccharides 3. If you perform several qualitative tests on an unknown food item and get the following results, what can you conclude about that food item? Address what the results of each test reveal about the food item. Benedicts test (+), Barfoeds test (+), Bials Test (-) Seliwanoffs test (+) and Iodine test (-) _________ 4. Human beings dont have the enzymes necessary for the hydrolysis of the 1, 4-O-glycosidic linkages between molecules of glucose. That is why we cannot digest this compound and it is part of some laxatives. a. cellulose b. glycogen c. amylose d. amylopectin 5. The pentose sugar present mainly in the heart muscle a. Lyxose b. Ribose c. Arabinose d. Xylose 6. Two sugars which differ from one another only in configuration around a single carbon atom are termed a. Epimers b. Anomers c. Optical isomers d. Stereoisomers 7. The most important epimer of glucose is a. Galactose b. Fructose c. Arabinose d. Xylose 8. Compounds having the same structural formula but differing in spatial configuration are known as a. Stereoisomers b. Anomers c. Optical isomers d. Epimers 9. The carbohydrate of the blood group substances is a. Sucrose b. Fucose c. Arabinose d. Maltose 10. A sugar alcohol is a. Mannitol b. Trehalose c. Xylulose d. Arabinose
11. Which of the following is a non-reducing sugar? a. Isomaltose b. Maltose c. Lactose d. Trehalose 12. The heteropolysaccharide used for intravenous infusion as plasma substitute is a. Agar b. Inulin c. Pectin d. Starch 13. Which of the following is a heteroglycan? a. Dextrins b. Agar c. Inulin d. Chitin 14. Osazones are not formed with the a. Glucose b. Fructose c. Sucrose d. Lactose 15. Maltose can be formed by hydrolysis of a. Starch b. Dextrin c. Glycogen d. All of these 16. A carbohydrate, commonly known as dextrose is a. Dextrin b. D-Fructose c. D-Glucose d. Glycogen 17. Iodine gives a red colour with a. Starch b. Dextrin c. Glycogen d. Inulin 18. The highest concentrations of fructose are found in a. Aqueous humor b. Vitreous humor c. Synovial fluid d. Seminal fluid 19. Glucose uptake by liver cells is a. Energy-consuming b. A saturable process c. Insulin-dependent d. Insulin-independent 20. Mucopolysaccharides are a. Homopolysaccharides b. Heteropolysaccharides c. Proteins d. Amino acids 21. The distinguishing test between monosaccharides and dissaccharides is a. Bials test
b. Selwanoffs test c. Barfoeds test d. Hydrolysis test 22. Iodine solution produces no color with a. Cellulose b. Starch c. Dextrin d. Glycogen Answers 1d 2d 3 Fructose 4a 5a 6a 7a 8a 9b 10a 11d 12a 13b 14d 15d 16c 17c 18d 19d 20b 21c 22a

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UNIT 1: BIOCHEMISTRY

[Helps in what dept we have to read on Carbohydrates]

Previous CSIR Exams Questions on Carbohydrates

UNIT 1: BIOCHEMISTRY MCQ for Practice on Carbohydrates

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