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carbohydrate Chemistry
The document covers the chemistry of carbohydrates, focusing on their classification, isomerism, functional groups, and importance in biological systems. It details different types of carbohydrates including monosaccharides, oligosaccharides, and polysaccharides, along with their structural features and reactions. Additionally, it discusses important carbohydrates like glucose, fructose, and galactose, including their properties and roles in metabolism.
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carbohydrate Chemistry
- 1. CHEMISTRY OF CARBOHYDRATES PRESENTEDBY: MR.MOTE G.D. AGCOP,SATARA 1
- 2. OBJECTIVES Introduction and Definition Isomerismin Sugars Classification Important Carbohydrates Biomedical Importance of Carbohydrates 2
- 3. INTRODUCTION Hydrates of carbon Saccharides— sugars Some contain N and S Synthesized in Plants Animals 3
- 4. DEFINITION Carbohydrates are polyhydroxylatedcompounds having at least 3 carbon atoms and a potentially active carbonyl group which may be an aldose or a ketose group. Examples are: glucose, ribose. 4
- 5. GLUCOSE CHO C OHH C HHO COHH C OHH CH2OH D-Glucose 5
- 6. ANOMERIC CARBON ATOM Thecarbon atom which is part of the carbonyl group Alpha( )α and Beta( )β anomers differ from each other only in respect to configuration around anomeric carbon atom. 6
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- 8. ISOMERISM IN SUGARS Isomers/Stereo-isomers: Compounds having the same chemical formulae but differing in the arrangement of their atoms in space and having different physical properties are called isomers. 8
- 9. Mutarotation Defination:The optical rotationis changes gradualy until constant rotation is attained this phenomenon is also known as Mutarotaion e.g: glucose is dissolved in water,its optical rotation gradualy changes from 111° to 52.5 when solution is allowed to stand Key features: All reducing sugars exhibit mutarotation The phenomenon of mutarotation occures slowly in aqueous medium Mutarotation study can be done by changing NMR,IR,Mass Spectra 9
- 10. EPIMERS Monosaccharides which differin configuration around one specific C-atom are called epimers of one another C-2 epimers glucose and mannose C-4 epimers glucose and galactose 10
- 11. H C O HC OH HO C H H C OH H C OH CH2OH D-GLUCOSE H C O HO C H HO C H H C OH H C OH CH2OH D-MANNOSE CARBON-2 EPIMERS 11
- 12. CARBON-4 EPIMERS H CO H C OH HO C H H C OH H C OH CH2OH D-GLUCOSE H C O H C OH HO C H HO C H H C OH CH2OH D-GALACTOSE 12
- 13. Carbohydrates Monosaccharides Oligosaccharides Derived DisaccharidesCarbohydrates Aldoses Ketoses Oxidation Polysaccharides Reduction Amino sugars Homopolysaccharides Deoxy sugars CLASSIFICATION OF CARBOHYDRATES 13
- 14. MONOSACCHARIDES No of C-atomsPotentially active carbonyl group Trioses Tetroses Pentoses Aldoses Ketoses Hexoses Heptoses “These carbohydrates cannot Octoses be hydrolyzed into simpler compounds” 14
- 15. Aldehyde CHO KetoneC O15
- 16. Reducing and Non-ReducingSugars Reduction is the chemist’s term for electron gain A molecule that gains an electron is thus…… “reduced” A molecule that donates electrons is called a…… “reducing agent” A sugar that donates electrons is called a…… “reducing sugar” The electron is donated by the carbonyl group Benedict’s reagent changes colour when exposed to a reducing agent 16
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- 18. Benedict’s Test Benedict’sreagent undergoes a complex colour change when it is reduced The intensity of the colour change is proportional to the concentration of reducing sugar present The colour change sequence is: Blue… green… yellow… orange… brick red 18
- 19. The carbonyl group- monosaccharides The carbonyl group is “free” in the straight chain form But not free in the ring form BUT remember – the ring form and the straight chain form are interchangeable So all monosaccharides are reducing sugars All monosaccharides reduce Benedict’s reagent 19
- 20. The carbonyl group– disaccharides - sucrose In some disaccharides e.g. sucrose both of the carbonyl groups are involved in the glycosidic bond So there are no free carbonyl groups Such sugars are called non- reducing sugars They do NOT reduce Benedict’s reagent 20
- 21. The carbonyl group– disaccharides - sucrose The subunits of sucrose (glucose and fructose) are reducing sugars If sucrose is hydrolysed the subunit can then act as reducing sugars This is done in the lab by acid hydrolysis After acid hydrolysis sucrose will reduce Benedict’s reagent 21
- 22. OLIGOSACCHARIDES These are thecondensation products of 2 to 10 monosaccharide units Disaccharides: These are the condensation products of two monosaccharide units e.g. sucrose, lactose. 22
- 23. POLYSACCHARIDES These are thecondensation products of more than 10 molecules of monosaccharide units They include starch, glycogen. Stores of fuel Structural elements of cells 23
- 24. POLYSACCHARIDES Homopolysaccharides Heteropolysaccharides *Starch *Glycogen Glycoseaminoglycans *Cellulose Mucilages *Dextrins*Hyaluronic acid *Heparin *Agar *Chondoitin SO4 *Vegetable *Serum mucoids gums *Blood gp *Pectins polysaccharides *Hemicellulose 24
- 25. DERIVED CARBOHYRATES Oxidation ReductionAmino Deoxy Products Products Sugars Sugars Gluconic acid Glycerol Glucosamine Glucuronic acid Ribitol Galactoseamine Glucaric acid Mannoseamine Deoxyribose “These are derived from carbohydrates by various chemical reactions” 25
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- 27. IMPORTANT CARBOHYDRATES MONOSACCHARIDES PENTOSES Ribose: Found innucleic acids Forms structural elements of nucleic acid and coenzymes Intermediates of pentose phosphate pathway ATP, NAD, NADP, flavoproteins etc 27
- 28. HEXOSES Glucose Foundin fruits, fruit juices, hydrolysis of starch, maltose and lactose. Body sugar and the principal one used by the tissues Excess in the blood is called hyperglycemia and presence in urine (glucosuria) indicates diabetes mellitus Cataract due to sorbitol 28
- 29. Fructose Latin word forfruit — "fructus" Found in fruit juices, honey Released by the hydrolysis of inulin Main nutritional source of energy for the spermatozoa and is found in the seminal fluid Can be converted to glucose in the liver It is the sweetest sugar Lack of enzymes of metabolism can lead to essential fructosuria 29
- 30. Galactose Greek word formilk--"galact", found as a component of lactose in milk Formed by the hydrolysis of lactose Synthesized in the lactating mammary gland Constituent of glycolipids and glycoproteins Can be converted to glucose in the liver Accumulation can lead to galactosemia and cataract (galactitol) 30
- 31.
- 32. OLIGOSACCHARIDES Sucrose Known astable sugar -D-glucose ------ -D- fructoseα β -1 -2α β Sucrose α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside 32
- 33. Commonly known asmalt sugar. Present in germinating grain. Produced commercially by hydrolysis of starch. Maltose 33
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- 35. Commercially known asmilk sugar. Bacteria cause fermentation of lactose forming lactic acid. When these reaction occur ,it changes the taste to a sour one. Lactose 35
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- 37. Glycosidic linkage betweenglucose 37
- 38. HOMOPOLYSACCHARIDES Starch Main storageform of glucose in plants Polysaccharide units • Amylose (20—28%) • Amylopectin 72—80%) Polymer of -D-glucoseα -1 4 glycosidic linkageα At branching points -1 6 linkageα No free aldehyde group Found in wheat, rice, corn, potatoes38
- 39.
- 40. Form Linear Branch Linkageα-1,4 (some α- 1,6) α-1,4; α- 1,6 Polymer units 200-2,000 Up to 2,000,000 Molecular weight Generally <0.5 million 50-500 million Gel formation Firm Non- gelling to soft Characteristics of Amylose and Amylopectin Characteristic Amylose Amylopectin 40
- 41. Glycogen Known asanimal starch Present in the liver and muscle Both -1 4 and -1-6 linkages are foundα α More branched structure than starch Gives red color with iodine 41
- 42.
- 43. Reactions of Monosacharides OH H CH2OH H OH H OH OH H D-Glucose CHO COHH C HHO C OHH C OHH CH2OH D-Glucose CH2OH C OHH C HHO C OHH C OHH CH2OH D-Sorbitol NaBH4 Reduction: 43
- 44. Reactions of monosacharides Oxidation: CHO COHH C HHO C OHH C OHH CH2OH D-Glucose O COOH C OHH C HHO C OHH C OHH CH2OH Gluconic Acid OC C OHH C HHO CH C OHH CH2OH lactone NaBH4 CH2OH C OHH C HHO C OHH C OHH CH2OH D-Sorbitol44
- 45. Reactions of Monosacharides: OH H CH2OH H OH H OH OH H D-Glucose H3CC O C OH3C Acetic anhydride CH3CN HOAc H CH2OAc H OAc H CH2OAc OAc H Penta-o-acetyl-D-Glucose CHO C OHH C HHO C OHH C OHH CH2OH D-Glucose CH3OH HCl H CH2OH H OH H OH OH H OCH3 H Methyl glucopyranoside Glycoside formation: Acetylation Reaction: 45
- 46. Reactions of Monosacharides O H H H OH H OH H HO D-Glucose CH2OH H H2SO4 Heat O C O HHOH2C 5-HydroxymethylFurfural Action of acid: Action of base: CHO C OHH HC OH C OHH C OHH CH2OH 2(D-Glucose) Dil NaOH Warm CHO C HHO HC OH C OHH C OHH CH2OH D-Mannose CH2OH C O HC OH C OHH C OHH CH2OH D-Fructose 46
- 47. Reactions of Monosacharides: Fermentation: C6H12O6C2H5OH+2CO2 Glucose ethylalcohol 47
- 48. Constitution of Glucose: Molecular formula: C6H12O6 Pressence of Aldehude Group:glucose reacts with phenyl hydrazine to form phenyl hydrazone.this reaction indicate the pressence of a carbonyl group. Pressence of 5-OH groups:when glucose reacts with acetic anhydride in presence of pyridine to form glucose pentaacetate is formed .this indicates presence of Hydroxyl group Presence of straight chain of carbon atoms:when glucose is reduced with hydrogen in the presence of nickel catalyst gives sorbitol and reduction with HI gives n-hexane .this reaction indicates that the six carbon atoms present in glucose. Open chain structure of Glucose: 1. glucose contains a straight chain of six carbon atom 2. One end of carbon atom is aldehyde and other is alcohol 3. Remaining four carbon atom carries a hydrogen atom and hydroxyl group. 48
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- 79. Fructose: Preparation:fructose may beprepared in the laboratory by hydolysis of sucrose with dilute sulphuric acid C12H22O11 +H2O C6H12O6+C6H12O6 Sucrose water glucose fructose 79
- 80. Reactions of fructose: 1.Reaction with hydrogen cyanide:Fructose yields a cyanohydrin with hydrogen cyanide gives fructose cyanohydrin CH2OH C O HC OH C OHH C OHH CH2OH D-Fructose HCN CH2OH C OH HC OH C OHH C OHH CH2OH Fructose cyanohydrin NC 80
- 81. Reaction with hydroxylamines Fructosereacts with hydroxylamine to yeild an oxime CH2OH C O HC OH C OHH C OHH CH2OH D-Fructose NH2OH CH2OH C NOH HC OH C OHH C OHH CH2OH Fructose oxime 81
- 82. Reaction with phenylhydrazine Ontreatment with equimolar quantities of phenyl hydrazine gives phenyl hydrazone CH2OH C O HC OH C OHH C OHH CH2OH D-Fructose C6H5NHNH2 CH2OH C NNHC6H5 HC OH C OHH C OHH CH2OH Fructose phenyl hydrazone 82
- 83. Reduction: CH2OH C O HC OH COHH C OHH CH2OH D-Fructose 2H CH2OH C OHH C HHO C OHH C OHH CH2OH Sorbitol CH2OH C HHO C HHO C OHH C OHH CH2OH Mannitol 83
- 84. Oxidation: CH2OH C O HC OH COHH C OHH CH2OH D-Fructose Br2 COOH (CHOH)3 COOH CO2 + H2O Trihydroxy glutaric acid 84
- 85. Acetylation: CH2OH C O HC OH COHH C OHH CH2OH D-Fructose 5(CH3CO)2O CH2OOCH3 C O HC OOCH3 C OOCH3H C OOCH3H CH2OOCH3 Fructose pentacetate 85
- 86. Reaction with alcohol CH2OH CO HC OH C OHH C OHH CH2OH D-Fructose CH3OH CH2OCH3 C O HC OH C OHH C OHH CH2OH Fructoside 86
- 87.
- 88. Fructose alsoknown as levulose or fruit sugar is found in many fruits and in honey. It occur in combination with glucose in cane and beet sugars. The most important source of fructose is the polysaccharide inulin. Commercially, fructose is obtained by the hydrolysis of inulin. Crystalline D-fructose melts at 1040 c, it is the sweetest of the sugars, but is seldom used in pure form .it exibits mutarotation; the specific rotation values of alfa- and beta – and equilibrium mixture are -210 , 133.50 and -92.30 ; respetively. 88
- 89. Fructose respondsmost of the usual properties of the ketonic and hydroxyl groups. A very important property of the fructose is that although it has no aldehydic group ,it reduces fehling solution and Tollen’s reagent. This reducing property of fructose is said to be due to the presence on an α-hydroxy ketonic group which is readily oxidised by fehling and Tollen’s reagent. Tartaric acid 89
- 90. Fructose froman insoluble calicium fructosate with lime water (difference from glucose) . This fact is utilised in the separation of glucose and fructose by the hydrolysis of sucrose. CONSTITUTION OF FRUCTOSE : From the qualitative and quantitative analysis ,fructose is found to have its molecular formula as C6H12O6 Fructose is found to have five hydroxyl groups on five different carbon atoms . 90
- 91. Fructose formsa cyanohydrin and an oxime indicating the presence of carbonyl group, since fructose on oxidation with nitric acid gives a mixture of tartaric acid and glycolic acid (each having lesser number of carbon atoms), the carbonyl group is ketonic in nature. The formation of glycolic and tartaric acids indicates that the ketonic group is present at second position. 91
- 92. On reducingwith sodium amalgam and water, fructose gives hexahydric acid and sorbitol and mannitol. Which on further reduction with hydriodic acid and red phosphorus gives 2-iodohexane and n-hexane which suggest that in fructose molecule the six carbon atoms are present in a straight chain. 92
- 93. Fructose ontreatment with hydrogen cyanide gives cyanohydrin which on hydrolysis followed by reduction hydriodic acid and red phosphorus give n- butylmethylacetic acid, CH3CH2CH2CH2CH(CH3).COOH The formation of this compound again indicates that the ketonic group present at second position .The straight chain structure of fructose may be written as n-butylmethylacetic acid Fructose93
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- 95. CONFIGURATION OFFRUCTOSE: Since the above structure has three asymmetric carbon atoms it may exist in eight (2 3 =8) optical isomers. The exact configuration of the fructose is established by that it forms the same osazone as glucose indicating there by that the configurations of C3to C6 atoms of fructose is same as that of glucose. Hence the complete open-chain formula of fructose may be written as below. 95
- 96. RING STRUCTUREOF FRUCTOSE: Fructose exhibits mutarotation and forms two methyl fructosides. That is α and β forms. The commercial and natural free fructose is most probably β- isomer with a pyranose ring. But the fructose found in sucrose (a disaccharide) and inulin (a polysaccharide) is present inn furanose ring which during hydrolysis is converted into more stable pyranose form. Lastly , since the fructose is laevorotatory and has D- configuration of glucose ,it is denoted by D(-)-fructose. D-Fructose96
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- 98. Sucrose isthe commonest sugar known. The most common sources are sugar cane and sugar beets and other sources are maple saps, honey and fruit juices. The use of sugar is as food in various forms. The molecular formula is C12H22O11 On hydrolysis with acids or enzymes, sucrose gives equal parts of glucose and fructose; which thus constitute the two monosaccharides units of sucrose. 98
- 99. Sucrose neitherreacts with phenylhydrazine nor reduce Fehling’s solution indicating that the carbonyl group of the both monosaccharides involved in linkage. The glucose linked via its to the of fructose. Sucrose is hydrolysed by maltase but not by emulsin , thus indicating an alfa-D –glucose unit. Sucrose is also hydrolysed by an enzyme takainvertase thus indicates the beta-D-fructofuranose unit in sucrose. 99
- 100. The identities ofthese products demonstrate that the glucose portion is a pyranoside(1:5 linkage) and that the fructose portion is a furanoside(2:5 linkage) 100
- 101. Confirmation of Sucrose The structure of sucrose has been confirmed by several physical and chemical evidences. Determination of stereochemistry of D-glucoside and D-fructoside linkage is complicated by the fact that both linkages are hydrolyzed at the same time. The structure of sucrose has been confirmed by X-ray analysis The X-ray analysis of susrose sodium bromide dihydrate confirmed the stereochecal configuration found chemically ,and also the five membered ring of fructose. 101
- 102. Periodic acid method: Periodate oxidation conforms the structure of sucrose by following reaction. When sucrose is treated with three moles of periodic acid , one mole of formic acid and one mole of a tetra-aldehydes are formed . The Latter compound on oxidation with bromine water follwed by acid hydrolysis yields a mixture of glyoxylic , glyceric and hydroxypyruvic acids. 102
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- 105. Lactose occures inmammalian milk, e.g.,cow’s milk contains 4 to 6 % and human milk conains 5 to 8% of this sugar. Lactose molecular formula is C12H22O11 Lactose reduces on fehling’s solution, Tollen’s solution and benedict’s solution, it forms an osazone and exhibits mutarotation. Therfore, lactose must possess at least one carbonyl group which is not involved in he disaccharide linkage. 105
- 106. On acidicor enzymatic (lactase) hydrolysis lactose gives equimolar amounts of glucose and galactose. 106
- 107. Since lactose ishydrolysed only by lactase(identical with emulisin) the two monosaccharide units are linked through beta –glycosidic linkage. This is also indicated by its low specific rotation. Lactose 107
- 108. When lactoseis methylated, it yields methyl heptamethyl lactose which, on vigorous hydrolysis, yields 2,3,6-tri-o-mehyl-D-glucose and 2,3,4,6- tetra-O-methyl-D-galactose. The formation of these products reveals that glucose is the reducing half. 108
- 109. When lactose isoxidised by bromine water, it yields lactobionic acid which, on methylation and hydrolysis yields 2,3,5,6-tetra-O-methyl-D-gluconic acid and 2,3,5,6-tetra-O- methyl-D-galactose. 109
- 110. The formationof these products reveals that in lactose C-1 of glucose is linked to C-4 of galactose. This further reveals that glucose is a reducing part and D-galactose in non-reducing part in lactose. The point of linkage (C-4) of galactose unit is further confirmed by osazone formation. 110
- 111. When lactosazoneis subjected to acid hydrolysis, it yields D-galactose and D-glucosazone. This reaction show that in lactose it is the glucose unit which possesses a reducing group 111
- 112. Conformation structure oflactose. 112
- 113. Structural elucidation ofmaltose: 113
- 114. Maltose: It is alsoknown as malt sugar It is diasachride obtained by careful hydrolysis of starch in aqueous acid Maltose is also formed in one stage of the fermentation of of starch to ethyl alcohol,here hydrolysis is catalysed by enzyme diastase Maltose is white crysatlline solid,m.p.160-165°c It is soluble in water and is dextrorotatory 114
- 115. Constitution of maltose Molecular formula of maltose has been found to be C12H22O11 maltose is reducing sugar because it reduces Benidicts,Tollen’s and Fehling reagent. It reacts with phenyl hydrazine to form osazone When maltsoe is oxidized in presence bromine to form monocarboxylic acid(maltonic acid) When maltose is hydrolyzed in aqueous acid it yields two molecules of glucose C12H22O11 C6H12O6 + C6H12O6 115
- 116. Constitution of maltose Methylationof maltonic acid followed by acid hydrolysis gives 2,3,4,6 tetra-o-methyl-D-glucose and 2,3,5,6-tetra-o- methyl-D-gluconic acid indicates that in first product having free OH group at 5th position and second product having free OH group at 4th position which are involved in glycosidic linkage. Presence of free OH group indicates reducing sugar 116
- 117. General methods employedfor elucidation of polysacharides 1) Acid hydrolysis 2) Acetolysis 3) Enzyme hydrolysis 4) Methylation 5) Periodic oxidation 6) Molecular weight determination 117
- 118. General methods employedfor elucidation of polysacharides 1) Acid hydrolysis:A polysaccharide on treatment with acid undergoes complete hydrolysis to yield monosacharide units which can be identified by chromatographic technique.e.g.paper chromatography 2) Acetolysis:in this method,a polysacharide is subjected to simultaneous acetylation and hydrolysis 118
- 119. General methods employedfor elucidation of polysacharides 3) Enzyme hydrolysis:Enzyme are specific in their action,their for their action on polysacharide gives idea about the configuration of glycosidic linkage 4) Methylation:methylation of polysacharide is done by adding barium oxide and methyl iodide to the solution of polysachrides. the completion of methylation is confirmed by the absence of hydroxyl bond in the infrared spectrum.methylation of sugar gives information about the point of attachment of the sugar units through the glycosidic linkage 119
- 120. General methods employedfor elucidation of polysacharides 5) Periodic oxidation:it is most important method for establishing the mode of linkage in di and polysacharides.it yeilds different products in 1-2 linkage,1-3 linkage,1-4 linkage,1-6 linkage. This method involves the oxidation of the polysachride molecule followed by reduction to yield fragments that reveal the mode of linkgae present in original polysacharide 120
- 121. General methods employedfor elucidation of polysacharides 6) Molecular weight determination:it gives information about number of sugar molecule in polysachride.the various physical and chemical methods which are used for measuring the molecular weight of polysacharides.e.g.viscosity, osmotic pressure, sedimentation, light scattering,X-ray,electrophoresis. 121
- 122. Constitution of cellulose Molecularformula (C6H10O5)n When cellulose is hydrolysed with hydrochloric acid gives D- glucose.this reaction reveals that cellulose is made up of glucose unit As methylation,acetlyation and nitration of cellulose produce a trisubstitution product Fully methylated cellulose,when subjected to hydrolysis yeilds 2,3,6 tri-o-methyl-D-glucose .it reveals that the three free hydroxyl groups in each glucose When cellulose is dissloved in water it produces colloidal solution,this reveals that cellulose is a linear molecule 122
- 123. Constitution of starch Molecularformula (C6H10O5)n When cellulose is hydrolysed with hydrochloric acid gives D- glucose.this reaction reveals that cellulose is made up of glucose unit As methylation,acetlyation and nitration of cellulose produce a trisubstitution product Fully methylated cellulose,when subjected to hydrolysis yeilds 2,3,6 tri-o-methyl-D-glucose .it reveals that the three free hydroxyl groups in each glucose Starch is hydrolysed by the enzyme called diastase to maltose.this reveals that starch contains maltose unit. 123
- 124. 124 Sr.No starch cellulose 1.Reserve food material in plant It chief component of wood 2 It can be seperated into two component,amylose and amylopectin It is single component 3. Amylose and amylopectin linked through α-glycosidic linkage It contains D-glucose interconnected by B- glucoside linkage 4. Amylose chain acquire helical structure Cellulose acquire rope like structure 5. It gives blue color with Iodine It doesnot give blue color with iodine
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- 126. GLYCOSIDES A glycoside isan organic compound, usually of plant origin, that is composed of a sugar portion linked to a non-sugar moiety. The sugar portion is called glycone, while the non- sugar portion is called aglycone . 126
- 127. GLYCOSIDES The linkage betweenthe sugar and the aglycone is an acetal linkage. Types of Glycosides : According to atoms involved in the glycosidic linkage: 1- O-glycosides 2- C-glycosides 3- S-glycosides 4- N-glycosides 127
- 128. GLYCOSIDES Cardiac glycosidesDigitalis useful in Congestive cardiac failure. They contain Steroid as aglycone. 128
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- 130. BIOMEDICAL IMPORTANCE Glucose— most important carbohydrate Glucose can be converted into • glycogen • ribose • galactose Glycoproteins — molecular targeting Antibodies and blood clotting factors Structural components of cell membranes 130
- 131. Neuronal adhesion indevelopment of nervous system (protein-glycan-heparan-sulfate) Constituents of extra cellular matrix Diseases associated with carbohydrates • Diabetes mellitus • Galactosemia • Lactose intolerance • Glycogen storage diseases 131
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