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Carbohydrates Structure and Classification  Term Carbohydrate Is Derived from the French: HYDRATE DE CARBONE  Compounds Composed of C, H, and O

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Carbohydrates Structure And Classification Term carbohydrate is derived from the French: HYDRATE DE CARBONE compounds composed of C, H, and O (CH2O)n when n = 5 then C5H10O5 not all carbohydrates have this empirical formula: deoxysugars, aminosugars carbohydrates are the most abundant compounds found in nature (cellulose: 100 billion tons annually) CARBOHYDRATES Polyhydroxy aldehydes or ketones, or substances that yield these compounds on hydrolysis Aldehyde O H group Both can be C CH2OH written Keto C H O or H- C - OH 3 6 3 C O group (CH2O)3 CH2OH CH2OH Glyceraldehyde Dihydroxyacetone Carbohydrate with an aldehyde group: Aldose Carbohydrate with a ketone group: Ketose Empirical formula of many simpler carbohydrates: (CH2O)n (hence the name hydrate of carbon) Characteristic Most carbohydrates are found naturally in bound form rather than as simple sugars Polysaccharides (starch, cellulose, inulin, gums) Glycoproteins and proteoglycans (hormones, blood group substances, antibodies) Glycolipids (cerebrosides, gangliosides) Glycosides Mucopolysaccharides (hyaluronic acid) Nucleic acids Function A storage form of energy in the body. Cell surface recognition receptors (by other cells, hormones, viruses) Cell surface antigens, e.g. blood groups. Gastric glycoprotein (mucin) contains more than 60% carbohydrate. A structural component of many organisms: a) cell walls of bacteria b) exoskeleton of insects c) cellulose of plants. intermediates in the biosynthesis of other basic biochemical entities (fats and proteins) associated with other entities such as glycosides, vitamins and antibiotics) participate in biological transport, cell-cell recognition, activation of growth factors, modulation of the immune system, lubrication of skeletal joints Classification and Nomenclature of Carbohydrates • Monosaccharides (monoses or glycoses) Trioses, tetroses, pentoses, hexoses Oligosaccharides Di, tri, tetra, penta, up to 9 or 10 Most important are the disaccharides Polysaccharides or glycans Homo and Heteropolysaccharides Complex carbohydrates Derived carbohydrate Oxidation product- Ascorbic acid Reducing product- glycerol Amino sugar- glucosamin Deoxy sugars- deoxyribose Monosaccharides Polyhydroxy aldehydes or ketones that can’t easily be further hydrolyzed “Simple sugars” Number of carbons Name Example 3 Trioses Glyceraldehyde 4 Tetroses Erythrose 5 Pentoses Ribose 6 Hexoses Glucose, Fructose 7 Heptoses Sedoheptulose 9 Nonoses Neuraminic acid Classification According to the Functional Group a) Aldoses b) Ketoses Functional Sugar No of Carbons Name of Group Class Sugar Aldehyde Aldose 3 (aldotriose) Glycerose 4 (aldotetrose) Erythrose 5 (aldopentose) Ribose 6 (aldohexose) Glucose Galactose Mannose Ketone Ketose 3 (ketotriose) Dihydroxyacetone 4 (ketotetrose) Erythrulose 5 ketopentose) Xylulose 6 (ketohexose) Fructose 7 Ketopeptose Sedoheptulose Examples For Monosaccharide Glucose (Dextrose); Grape sugar: Glucose is the most important carbohydrate in biology The cell uses it as a source of energy and metabolic intermediate. Glucose is produced in the process ofphotosynthesis, and is used in both prokaryotes and eukaryotes. CHO H-C-OH HO-C- H H-C- OH H-C- OH CH2OH Fructose (Levulose); Fruit sugar Found in honey & fruits. Fructose is produced from the digestion of sucrose (a disaccharide consisting of glucose and fructose). Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose Galactose It is a sugar found in dairy products,in the form of Lactose. It is a disaccharide formed of Glucose & Galactose. It forms part of glycolipids and glycoproteins in several tissues of the body CHO H-C-OH HO-C- H HO-C- H H-C- OH CH2OH Oligosaccharides Hydrolyzable polymers of 2-6 monosaccharides Disaccharides composed of 2 monosaccharides Examples: Sucrose, Lactose Disaccharides Disaccharides are produced from the condensation of 2 monosaccharide molecules. Lactose [milk sugar] is formed in the mammary gland. It is composed of galactose and glucose. Maltose (Malt sugar) is composed of 2 molecules of glucose. Sucrose (Table sugar, Cane sugar, Beet sugar) is composed of glucose and fructose DISACCHARIDES SUCROSE Sucrose: the most widely occurring disaccharide of ordinary table sugar. Structure: 6 CH OH 2 1 O HOH C H 5 O 2 From H 2 5 From H H OH 6 D-glucose 4 H C OH 1 CH2OH D-fructose 3 4 OH 3 O 2 OH H H OH ¦Á-Glucosidic linkage -Glucosidic linkage MALTOSE Structure: 6 CH2OH 6 CH2OH H 5 O H O HO H 5 H H 4 OH H C C 1 1 4 OH H 3 OH O 3 2 2 H H OH H OH ¦Á-Glucosidic linkage or HOH2C O HO HO HOH2C O OH O HO OH OH CELLOBIOSE Structure: 6 ¦Â-Glycosidic linkage CH2OH 5 OH H O H 6CH2OH OH H 1 4 H O O H5 3 2 H 4 C OH H 1 H OH H OH 3 2 H OH LACTOSE Lactose is a reducing sugar that hydrolyzes to yield D-glucose and D-galactose; the glycosidic linkage is β. Structure: ¦Â-Glucosidic linkage 6CH2OH 5 OH H O H From 6CH2OH OH H 1 4 D-glucose From OH O O H5 3 2 H D-galactose 4 C OH H 1 H OH H H 3 2 H OH or HO HOH C 2 O HOH2C O O HO OH HO OH OH Oligosaccharides…. It occurs in glycoproteins, which are proteins to which oligosaccharides are covalently attached. Example Made up of Trisaccharide Raffinose Fructose+ Galactose+ Glucose Tetrasaccharide Stachyose 2 Galactose+ Glucose+ Fructose Pentasaccharide Verbascose 3 Galactose+ Glucose+ Fructose Polysaccharide Homopolysaccharides: polysaccharides that are polymers of a single monosaccharide. Heteropolysaccharides: those made up of more than one type of monosaccharide. Glucan: a homopolysaccharide consisting of glucose monomeric units. Galactan: a homopolysaccharide consisting of galactose units Three important polysaccharides, all of which are glucans, glycogen, starch and cellulose. STARCH Heating starch with water produce amylose (10-20%)and amylopectin(80-90%). Structure of amylose: CH OH 2 CH2OH O H H O OH H H H C H OH OH H CH O HO n H OH H OH n > 1000 1:4-glycosidic linkages In amylopectin the chains are branched. Branching takes place between C-6 and C-1at intervals of 20-25 glucose units. Amylose • The amylose chain forms a helix. • This causes the blue colour change on reaction with iodine. • Amylose is poorly soluble in water, but forms micellar suspensions Partical structure of amylopectin: Branch CH OH 2 CH2OH H O H O H H OH OH H C H ¡• O OH H C O O H OH H OH 1:6 branch poinr Main chain CH OH H C 2 CH2OH 2 CH2OH H O H O H O H H H H O OH H H H OH H C OH H C H ¡• O OH H C O OH H C O O O ¡• H OH H OH H OH H OH The molecular weight is about 1-6 milion, include hundreds of interconnecting chains of 20-25 glucose units. Amylopectin • Amylopectin causes a red-violet colour change on reaction with iodine. • This change is usually masked by the much darker reaction of amylose to iodine. Amylopectin GLYCOGEN In glycogen the chain are much more highly branched and the molecular weight is very high. Polymer of α- 1→4 linked subunit and branching at α- 1→6 (similar to amylopectine) Highly branched The size and structure of glycogen suits its function: (1) Its size makes it too large to cross cell membranes. (2) The structure of glycogen solves the enormous of osmotic pressure within the cell. (3) The high branch structure of glycogen simplify the cell’s logistical problems. Glucose (from glycogen) is highly water soluble and as an ideal Source of “ready energy”. CELLULOSE CH2OH H O H O A portion of cellulose structure: CH2OH OH H H O O H H OH H C H OH n H H OH The glycosidic linkages are , 1: 4 Special property: The outside –OH groups are ideally situated to “zip” the chains make together by forming hydrogen bonds. Zipping many cellulose chains together in this way gives a highly insoluble. cellulose is found in its purest form from the seed hairs of cotton wood cellulose, on the other hand forms a composite with lignin and other polysaccharides Bacterial cellulose: Gluconacetobacter are involved in the production of a very peculiar form of cellulose Cellulose acetate: ester of cellulose Ethylcellulose: microencapsulated drug delivery systems Hydroxypropyl cellulose: soluble both in water and organic solvent, used as a lubricant, corneal erosions neuroparalytic keratitis Dextran In bacteria and yeast Made of α- 1→6 linked polyglucose and have α- 1→3 branches Synthetic dextran are used in several commercial products e.g. Sephadex Chitin Linear homopolysaccharide of N acetyl glucosamine residue in β- 1→4 linkage Heteropolysaccharides in the body are the glycosaminoglycans (GAGs). These molecules are long unbranched polysaccharides containing a repeating disaccharide unit. GAGs are highly negatively charged molecules, with extended conformation that imparts high viscosity to the solution. GAGs are located primarily on the surface of cells or in the extracellular matrix (ECM). Along with the high viscosity of GAGs comes low compressibility, which makes these molecules ideal for a lubricating fluid in the joints. At the same time, their rigidity provides structural integrity to cells and provides passageways between cells, allowing for cell migration. The disaccharide units contain either of two modified sugars, called amino sugars N-acetylgalactosamine (GalNAc) or N-acetylglucosamine (GlcNAc), and an acidic sugar uronic acid such as glucuronic acid or iduronic acid. The amino group is usually acetylated. This eliminates the positive charge. In some glycosaminoglycans, one or more of the hydroxyls of the amino sugar is esterified with sulfate. The combination of these sulfate groups and the carboxylate groups of the uronic acid residues gives the glycosaminoglycans a very high density of negative charge. Keratan sulfate is an exception in which galactose is present, instead of an acidic sugar. Hyaluronic acid does not contain sulfate.
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  • PENTOSE PHOSPHATE PATHWAY — Restricted for Students Enrolled in MCB102, UC Berkeley, Spring 2008 ONLY

    PENTOSE PHOSPHATE PATHWAY — Restricted for Students Enrolled in MCB102, UC Berkeley, Spring 2008 ONLY

    Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY Bryan Krantz: University of California, Berkeley MCB 102, Spring 2008, Metabolism Lecture 5 Reading: Ch. 14 of Principles of Biochemistry, “Glycolysis, Gluconeogenesis, & Pentose Phosphate Pathway.” PENTOSE PHOSPHATE PATHWAY This pathway produces ribose from glucose, and it also generates 2 NADPH. Two Phases: [1] Oxidative Phase & [2] Non-oxidative Phase + + Glucose 6-Phosphate + 2 NADP + H2O Ribose 5-Phosphate + 2 NADPH + CO2 + 2H ● What are pentoses? Why do we need them? ◦ DNA & RNA ◦ Cofactors in enzymes ● Where do we get them? Diet and from glucose (and other sugars) via the Pentose Phosphate Pathway. ● Is the Pentose Phosphate Pathway just about making ribose sugars from glucose? (1) Important for biosynthetic pathways using NADPH, and (2) a high cytosolic reducing potential from NADPH is sometimes required to advert oxidative damage by radicals, e.g., ● - ● O2 and H—O Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY Two Phases of the Pentose Pathway Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY NADPH vs. NADH Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY Oxidative Phase: Glucose-6-P Ribose-5-P Glucose 6-phosphate dehydrogenase. First enzymatic step in oxidative phase, converting NADP+ to NADPH. Glucose 6-phosphate + NADP+ 6-Phosphoglucono-δ-lactone + NADPH + H+ Mechanism. Oxidation reaction of C1 position. Hydride transfer to the NADP+, forming a lactone, which is an intra-molecular ester.