Chapter 22 Carbohydrates Lecture Notes
Chapter 22 –CarbohydratesChem 306RoperI.Carbohydrates – OverviewA. Carbohydrates are a class of biomolecules which have a variety of functions.1. energy2. energy storage3. structure4. other functions!B. Chemically speaking carbohydrates are polyhydroxyaldehydes, polyhydroxyketones,or compounds that yield them after hydrolysis.HHOHHOCHC OHC HC OHC OHCH2OHCH2OHC OH C OHHO C HH C OHCH2OHC. Carbohydrates are classified as monosaccharides, disaccharides, oligosaccharides,or polysaccharides.1
II.Monosaccharides – Properties and StructureA. Structure and Nomenclature1. Most monosaccharides have the formula CnH2nOn.2. The suffix “ose” indicates that a compound is a sugar while a numerical prefixindicates the number of carbon atoms in the chain.3. Monosaccharides containing an aldehyde group are classified as aldoses.Those containing a ketone group are called ketoses.2
B. Fischer Projection FormulasChemists commonly use two-dimensional representations called Fisherprojections to show the configuration of carbohydrates.C. D and L Monosaccharides1. The configuration of carbohydrates is commonly designated using the D and L systemproposed by Emil Fischer in 1891. At that time it was known that each enantiomer ofglyceraldehyde rotated plane polarized light the same number of degrees but in oppositedirections. There was no way to associate this property with molecular structure. Anarbitrary assignment of D and L was made.3
2. The family of D – aldoses4
3. The family D – ketoses4. Diastereomers5
D. Amino Sugars1. Amino sugars contain an amino (-NH2) group instead of a hydroxyl (-OH)group.2. Amino sugars are common in nature : D – glucosamine D – mannosamine ( a C – 2 stereoisomer of glucosamine) D – galactosamine (a C - 4 stereoisomer of glucosamine).HHOHHCHONH2HOHOHCH2OHD – glucosamineWhat is the structure of N – acetyl – D – glucosamine?6
E. Cyclic Structures1. Aldehyde (or ketone) alcohols hemiacetal2. Ring/cyclic hemiacetals are stable.3.Monosaccharides have hydroxyl and carbonyl groups in the same molecule.As a result, they exist almost exclusively as five and six-membered cyclichemiacetals (furanose and pyranose structures).7
CHOHHOHHOHHOHOHCH2OHD – glucoseHaworth Projection4. Drawing Haworth projections8Chair Conformation
5. Anomers and anomeric carbons6. Mutarotation – The change in specific rotation of plane polarized light thatoccurs when an or β form of a carbohydrate is converted to an equilibriumaqueous mixture of the two forms.9
F. MonosaccharidesA. PropertiesRelative Sweetness of Some Sugars and Sugar SubstitutesB. Monosaccharides to Know1. Glucosea. Glucose (dextrose) is the most widely occurring monosaccharide.b. D-glucose serves as a source of energy to fuel biochemical reactions.10
2. GalactoseD – galactose is widely distributed in plant gums and pectins and is foundin milk sugar (the disaccharide lactose). It is also synthesized in the bodyfrom glucose as a component of glycolipids and glycoproteins.3. FructoseD – fructose is found in honey, fruit, table sugar (the disaccharidesucrose), and sweetners (high fructose corn syrup).11
4. Ribose and DeoxyriboseThese two sugars are found in biomolecules such as ATP, coenzyme A, andnucleic acids (DNA and RNA).III.Reactions of MonosaccharidesA. Oxidation1. Review12
2. Reducing sugars3. In basic solution, all monosaccharides can undergo oxidation reactions.a. Open-chain aldose monosaccharides13
b. Open-chain ketose monosaccharidesc. Applications – Testing for glucose in urine1. Benedict’s Test2. Glucose Oxidase - Chemstrips and spectrophotometric analysisH OHglucose oxidaseHOHOHOHHOHH OHO2 H2OΒ – D – glucoseHHOHHCOOHOHHOHOHCH2OH H2O2D – gluconic acidNH2peroxidaseCH3colored product H2O22 - methyl aniline(o - toluidine)14
B. Reduction1. Review2. Reduction reaction3. Some common sugar alcoholsHHOHHCH2OHOHHOHOHCH2OHD - glucitol(D - D - mannitolxylitol15
C. Esterification – Formation of phosphoric estersHHOHHCHOOHHOHOHCH2OHD - HOH OCH2O P OOD - glucose - 6 - phosphateD. Formation of Acetals (glycosides)1. Review2. Glycoside Formation16OO P OHOHOHOHOHHOHHOH
3.The monosaccharides in disaccharides, oligosaccaharides, andpolysaccharides are linked by glycosidic bonds.4. Many glycosides are found in nature. Glycosides play numerous importantroles in living organisms. Many plants store important chemicals in the formof inactive glycosides; if these chemicals are needed, the glycosides arebrought in contact with water and an enzyme and the sugar part is broken off,making the chemical available for use. Many such plant glycosides are usedas medications.Digoxin – a cardiac glycosideCoumarin glycosidescoumarina coumarin glycoside17
IV.DisaccharidesA. Disaccharides contain a glycosidic linkage between the C1 of one sugar and anyposition on another sugar (often C4).B. Some disaccharidesMaltose18
LactoseSucrose19
C. Hydrolysis of DisaccharidesAcid or enzyme hydrolysis of disaccharides yields monosaccharide subunits.V.PolysaccharidesA. Polysaccharides are polymers containing 1000’s of monosaccharide subunits.B. They are not soluble in water but their many hydroxyl groups become hydrated andform thick suspensions.C. Do polysaccharides taste sweet?D. Are polysaccharides reducing sugars?E. Examples and reactions1. Cellulose and Starcha. Structure20
b. Hydrolysis of starch - corn syrup and high fructose corn syrup (HFCS)21
2. Glycogen3. Connective tissue and polysaccharides – Long unbranched polysaccharidesof modified glucose molecules (mucopolysaccardes) have several functionsas components of connective tissue.The building blocks of these polysaccharides are modified sugars.22
4. Gums – Gums are a mixture of oligosaccharides, polysaccharides, andglycoproteins. The specific compositions depends on the plant. Someexamples are xanthan gum, gum Arabic (gum acacia), gum tragacanth, andguar gum. Gums are often used in the food industry as thickeners,emulsifiers, and stabilizers. Artists use gum as film formers for paints andpastels.23
5. Heparin – Heparin is a polysaccharide that has an anticoagulant effect.VI.Carbohydrates as Cell Markers – Blood TypesWhy are people with blood type “O” considered to be universal blood donors?Why are people with blood type “AB” considered to be universal blood recipients?24
VII.Other ApplicationsA. BEANO –a “food enzyme dietary supplement” - galactosidase, sucraseB. Invert Sugar and InvertaseC. Olestra25
Chapter 22 -Carbohydrates Chem 306 Roper I. Carbohydrates - Overview A. Carbohydrates are a class of biomolecules which have a variety of functions. 1. energy 2. energy storage 3. structure 4. other functions! B. Chemically speaking carbohydrates are polyhydroxyaldehydes, polyhydroxyketones, or compounds that yield them after hydrolysis. CH
Introduction of Chemical Reaction Engineering Introduction about Chemical Engineering 0:31:15 0:31:09. Lecture 14 Lecture 15 Lecture 16 Lecture 17 Lecture 18 Lecture 19 Lecture 20 Lecture 21 Lecture 22 Lecture 23 Lecture 24 Lecture 25 Lecture 26 Lecture 27 Lecture 28 Lecture
Part One: Heir of Ash Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26 Chapter 27 Chapter 28 Chapter 29 Chapter 30 .
Complex Carbohydrates Include starches and some forms of fiber. About 50% of your diet should come from complex carbohydrates. Examples of foods containing complex carbohydrates include pasta, wheat, corn, vegetables, fruit, sweet potatoes, beans and grains. Simple carbohydrates Include sugars such as glucose, fructose and sucrose.
Chemistry 108 Chapter 12 Lecture Notes Carbohydrates 1 Chapter 12 Lecture Notes: Carbohydrates Educational Goals 1. Given a Fischer projection of a monosaccharide, classify it as either aldoses or ketoses. 2. Given a Fischer projection of a monosaccharide, classify it by the number of carbons it contains. 3. Given a Fischer projection of a monosaccharide, identify it as a D-sugar or L-sugar.
TO KILL A MOCKINGBIRD. Contents Dedication Epigraph Part One Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Part Two Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18. Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26
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Carbohydrates are, in fact, an essential part of our diet; grains, fruits, and vegetables are all natural sources of carbohydrates. Carbohydrates provide energy to the body, particularly through glucose, a simple sugar that is a component of starch and an ingredient in many staple foods. Carbohydrates also have other
and STM32F103xx advanced ARM-based 32-bit MCUs Introduction This reference manual targets application developers. It provides complete information on how to use the low-, medium- and high-density STM32F101xx, STM32F102xx and STM32F103xx microcontroller memory and peripherals. The low-, medium- and high-density STM32F101xx, STM32F102xx and STM32F103xx will be referred to as STM32F10xxx .
