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CARBOHYDRATES PREPARED BY Dr.V. SANGEETHA, Asst Professor & HOD, Department of Chemistry, Kongunadu Arts and Science College, Coimbatore - 29 LECTURE OUTLINE By the end of the lecture, the student should know: The Importance of carbohydrates. The Definition of Carbohydrates. The Classification of Carbohydrates. The Difference between various Isomers.. CARBOHYDRATE: IMPORTANCE Most Abundant Class of Biomolecules. An Important Macronutrient. Performs important physiological functions in the body. Associated with Pathological Conditions (Diabetes Mellitus, Lactose Intolerance). DEFINING CARBOHYDRATES Carbohydrates or Saccharides (Greek Sakcharon meaning "Sugar") Organic compounds composed of Carbon, Hydrogen and oxygen. Many Carbohydrates also contain Nitrogen and other elements. Carbohydrates derive their name from a Misleading Concept 'Hydrates of Carbon’ Hydrogen and Oxygen in Carbohydrates were found to be present in the same proportion as in water. (2:1).(E.g. Glucose C6H12O6 or C6 (H2O)6). It is due to this fact that compounds derived their name “Carbon Hydrate”. GLUCOSE H-C=O H-C-OH OH-C-H H-C-OH H-C-OH CH2OH This term is not a perfect derivation as many carbohydrates do not have the same proportion as water. Example: DEOXYRIBOSE (C5H10O4) H-C=O H-C-H H-C-OH H-C-OH CH2OH CHEMICAL DEFINITION OF CARBOHYDRATES Polyhydroxyl: Having more than one hydroxyl group. (-OH) Functional Group: It is a specific group of atoms or bonds which are part of a larger hydrocarbon chain.(Provide a specific chemical behaviour). For carbohydrates, the functional group is the carbonyl group which may be either Aldehyde Group (H-C=O) Or Keto Group (C=O) WHAT IS SIMILAR & DIFFERENT IN THESE TWO STRUCTURES? H-C=O CH2OH H-C-OH C=O More than one hydroxyl group in both OH-C-H OH-C-H H-C-OH H-C-OH CH2OH CH2OH WHAT IS COMMON & DIFFERENT IN THESE TWO STRUCTURES? H-C=O CH2OH H-C-OH C=O Carbonyl Group in both But? OH-C-H OH-C-H H-C-OH H-C-OH CH2OH CH2OH WHAT IS COMMON & DIFFERENT IN THESE TWO STRUCTURES? H-C=O CH2OH H-C-OH C=O Aldehyde in 1 and Ketone in 2 OH-C-H OH-C-H H-C-OH H-C-OH CH2OH CH2OH Carbohydrates are Polyhydroxy Alcohols with Carbonyl groups Which May Either Be Aldehyde (H-C=O) or Keto (C=O) Groups. H-C CH2OH CAN YOU O VISUALIZE H-C-OH C EITHER ALDEHYDE OH-C-H OH-C-H OR KETONE H-C-OH H-C-OH GROUP IN THIS H-C-OH H-C-OH POLYHYDROX Y ALCOHOL? CH2OH CH2OH H-C CH OH HOH 2 NO! BUT O HYDROLYSIS H-C-OH C OF THIS COMPOUND OH-C-H OH-C-H YIELDS TWO COMPOUNDS H-C-OH H-C-OH WITH ALDEHYDE H-C-OH H-C-OH OR KETONE GROUPS CH2OH CH2OH H-C =O CH OH HOH 2 NO! BUT O HYDROLYSIS H-C-OH O=C OF THIS COMPOUND OH-C-H OH-C-H YIELDS TWO COMPOUNDS H-C-OH H-C-OH WITH ALDEHYDE H-C-OH H-C-OH OR KETONE GROUPS CH2OH CH2OH MANY POLYHYDROXY ALCOHOLS MAY NOT HAVE AN ACTIVE ALDEHYDE OR KETONE GROUP BUT THEY MAY YIELD THEM ON HYDROLYSIS. THEY ARE ALSO DESIGNATED AS CARBOHYDRATES. THEREFORE, THE COMPLETE DEFINITION OF CARBOHDRATES IS: CARBOHYDRATES ARE POLYHYDROXYL ALCOHOLS WITH POTENTIALLY ACTIVE CARBONY GROUPS WHICH MAY BE EITHER AN ALDEHYDE OR KETONE GROUP. THEY ALSO CONTAIN THOSE COMPOUNDS, WHICH YIELD THEM ON HYDROLYSIS. CLASSIFICATION OF CARBOHYDRATES Carbohydrates are mainly classified into four different groups: Monosachharides Disaccharides Oligosaccharides Polysaccharides MONOSACCHARIDES Monosaccharides are those carbohydrates which Cannot be Hydrolyzed further into more simple carbohydrates. Thus, they are the Simplest form of Carbohydrates. Familiar examples are: Glucose, Fructose, Ribose & Galactose. MONOSACCHARIDES ARE FURTHER CLASSIFIED ON THE BASIS OF: Aldehyde or Ketone Group: Aldomonosaccharides (Aldoses). Ketomonosaccharides (Ketoses). Carbon Chain Length. Trioses. Tetroses. Pentoses. Hexoses. Heptoses. CARBONYL GROUP H-C=O CH2OH H-C-OH C=O OH-C-H GLUCOSE OH-C-H H-C-OH FRUCTOSE--> H-C-OH H-C-OH H-C-OH CH2OH CH2OH CARBON CHAIN H-C=O H-C=O H-C-OH OH-C-H OH-C-H GLUCOSE H-C-OH H-C-OH ARABINOSE--> H-C-OH H-C-OH CH2OH CH2OH EXAMPLES OF MONOSACCHARIDES NO. OF CARBON ALDO KETO ATOMS 3C TRIOSE GLYCERALDEHYDE DIHYDROXYACETON E 4C TETROSE ERYTHROSE ERYTHRULOSE 5C PENTOSE RIBOSE, XYLOSE RIBULOSE, XYLULLOSE 6C HEXOSE GLUCOSE, FRUCTOSE GALACTOSE, MANNOSE GLYCERALDEHYDE GLYCERALDEHYDE IS THE SIMPLEST MONOSACCHARIDE(PARTICULARLY ALDOSES) IT CANNOT BE HYDROLYZED FURTHER. IT IS THE SMALLEST POSSIBLE STRUCTURE THAT IS A CARBOHYDRATE CANNOT HAVE LESS THAN 3 CARBON ATOMS. GENERAL FORMULA OF MONOSACCHARIDE: (C•H2O)N (WHERE N IS ANY NUMBER OF THREE OR GREATER) ISOMERISM Isomers are basically molecules that have the same chemical formula but they differ in their chemical structures. Asymmetric Carbon is an important determinant of Isomerism. Asymmetric Carbon is that Carbon which is attached with four different groups. STRAIGHT CHAIN STRUCTURE OF TYPICAL MONOSACCHARIDE (GLUCOSE) Anomeric Carbon Epimeric Carbons Penultimate Carbon Terminal Alcohol Carbon THE ASSIGNMENT OF D OR L IS MADE ACCORDING TO THE ORIENTATION OF THE PENULTIMATE CARBON If the Hydroxyl Group is on the right the molecule is a D sugar, Otherwise It is an L sugar. OH H L-Sugar : D-Sugar D AND L ISOMERISM PRODUCE MIRROR IMAGES EPIMERISM Isomers which differ from each other only with regard to oh group on a single asymmetric carbon atom. OPTICAL ISOMERS When a beam of polarized light is passed through sugars, they will be rotated either towards right or left. Right Rotation (dextrorotatory) E.g. D- Glucose Left Rotation (levorotatory) E.g. D- Fructose MONOSACCHARIDE DERIVATIVES OF BIOLOGICAL IMPORTANCE Oxidation Products (Sugar Acids) Reduction Products (Sugar Alcohols). Amino Sugars. Sugar Phosphates. OXIDATION PRODUCTS (SUGAR ACIDS) When oxidized under proper conditions, Aldoses may form three types of acids (Sugar Acids): Uronic Acids. Aldonic acids. Saccharic Acids. Type of sugar Acid produced depends on which carbon is oxidized. H-C=O H-C-OH URONIC ACID OH-C-H Oxidation Of Aldose At Primary Alcohol H-C-OH (Terminal Carbon) H-C-OH CH2OHCOOH H-C=OCOOH ALDONIC ACID H-C-OH Oxidation Of Aldose At Carbonyl Carbon OH-C-H (Aldehyde Group) H-C-OH H-C-OH CH2OH H-C=OCOOH H-C-OH Saccharic Acid OH-C-H Oxidation Of Aldose At Both Aldehyde & H-C-OH Terminal Carbons H-C-OH CH2OHCOOH EXAMPLES OF ALDOSES WITH THEIR CORRESPONDING URONIC ACIDS ARE: Sugar Uronic Acids Glucose Glucuronic acid, Iduronic acid ------------- ---------------------- Mannose Mannuronic acid ------------- ---------------------- Galactose Galacturonic acid ------------- ------------------------ EXAMPLES OF ALDOSES WITH THEIR CORRESPONDING ALDONIC ACIDS ARE: Sugar Aldonic Acids Glucose Gluconic acid ------------- ---------------------- Mannose Mannonic acid ------------- ---------------------- Galactose Galactonic acid ------------- ------------------------ Amino Sugar: Substitution of Amino Group for a H-C=O Hydroxyl Group of a H-C-OHNH2 Sugar Results in the Formation of an OH-C-H Amino Sugar. H-C-OH The Amino Group is attached to H-C-OH Carbon 2. CH2OH COMMON EXAMPLES OF AMINO SUGARS (AMINOSACCHARIDES) Galactosamine Glucosamine SUGAR ALCOHOLS; REDUCTION PRODUCTS Sugar Alcohols are obtained by reduction of Monosaccharides (Both Aldoses and Ketoses) and disaccharides. Sugar alcohols, also known as Polyols, Polyhydric Alcohols, or Polyalcohols. SUGAR ALCOHOLS ARE THE HYDROGENATED FORMS OF THE ALDOSES OR KETOSES H- C=O + H 2 CH2OH H-C-OH H-C-OH OH-C-H OH-C-H H-C-OH H-C-OH H-C-OH H-C-OH CH OH 2 CH2OH Glucose Sorbitol Sugars with their Corresponding Alcohols Glyceraldehyde & Glycerol Dihydroxyacetone Glucose Sorbitol (Glucitol) Mannose Mannitol Fructose Sorbitol & Mannitol Galactose Dulcitol Ribose Ribitol Erythrose Erythritol Xylose Xylitol Lactose Lactitol Maltose Maltitol Sugar Phosphates Phosphate Esters formed by various Monosaccharides are of Great Importance in Metabolic Reactions. Sugar phosphates of biological importance. Ribose and Deoxyribose in Nucleic Acids are Phosphate Esters of these monosaccharides. Phosphates of Glucose, Fructose and Glyceraldehyde etc. are important intermediate compounds in carbohydrate metabolism of almost all the cells. DISACCHARIDES Two Joined Monosaccharides. Sucrose: Glucose + Fructose Maltose: Glucose + Glucose Lactose: Glucose + Galactose OLIGOSACCHARIDES Composed Of: Three To Ten Monosaccharide Units. E.g. Fructooligosaccharides POLYSACCHARIDES Larger Than Ten Monosaccharide Units. Can Reach Many Thousands Of Units. Homopolysaccharides. Heteropolysaccharides. HOMOPOLYSACCHARIDES Similar Types of Monosaccharide Units. Starch Glycogen Cellulose HETEROPOLYSACCHARIDES Different Types of Monosaccharide Units. Mucopolysaccharides (Glycosaminoglycans that contain galactose and amine sugars) Agar (Contains various sugars like Glucose, Galactose).
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  • DISSERTATION Presented in Partial Eulfillment of the Requirements For

    DISSERTATION Presented in Partial Eulfillment of the Requirements For

    ÎHTRATED AMD BENZYLATED .ALIXDÎHC ACIDS AMD IKEIR USE IN SYNTHESES DISSERTATION Presented in Partial Eulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State Universi ty B y ADEX ROSENTHAL, D.Sc., B.Ed. , M.Sc, The Ohio State University 19 52 Approved hy: Adviser 1 TABLE OF CONTENTS PART I Page I. OBJECTIVE..................................... 1 II. HISTORICAL.................................... 2 A . General.................................. 2 B. AldonicAcids and Their Lactones........ 3 C. Preparation of D-Gluconic and D- Galactonic Acids........................ 7 1, Commercial Preparation of D-Glu­ conic Acid by Fermentation Methods............. 7 2, Preparation of D-Galactonic Acid... 10 3, Chemical and Electrolytic Methods of Preparing Aldonic Acids........ 11 D . Preparation of Aldonamides.............. 14- E. Preparation of Sugar Nitrates 15 1. General............... 15 2. Nitration of Carbohydrates with Nitrogen Pentoxide.............. 18 (a) Nitrogen Pentoxide......,,..,, IS (b) Use of Nitrogen Pentoxide as a Nitrating Agent.......... 19 F . Fully 0—Esterifled Aldonic Acids....... 21 G. Reaction of Diazomethane with Sugar Acids....... 24. 1. Diazomethane..................... 24- 2. Action of Diazomethane on Aldonic Acids....................... 27 S81010 11 TABLE OF CONTENTS (cont.) Page H, Stabilizers of Nitrated Carbohydrates.. 27 I, Stability Tests of Nitrated Carbohydrates............................ 30 J. Double-Base Powders and Films........ 32 III. EXPERIMENTAL................................. 34 A. Synthesis of Methyl D-Galactonate Pentanitrate ....... 34 1. Preparation of D-Galactonamide 34 2. Attempted Nitration of D-Galac- tonamide with Nitric-Sulfuric Acids...... 35 3. Attempted Nitration of D-Galac— tonamide with Nitric-Acetic Acids,. 35 4. Preparation of Nitrogen Pentoxide,. 36 5. Synthesis of D—Galactonamide 0-Pentanitrate...... 3B 6. Synthesis of D-Galactonic Acid.,.., Pentanitrate..