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Day 1. Yao. Intro to Carbohydrates Introduction to Carbohydrates: Basic Concepts, Monosaccharides, Oligosaccharides, and Polysaccharides Dr. Yuan Yao Whistler Center for Carbohydrate Research October 1, 2019 2 History of Carbohydrate Uses & Knowledge 10,000 BCE Sugarcane processing in New Guinea 6000 BCE Sugarcane culture developed in India 6000 BCE Cellulose, as cotton, used by many cultures 4000 BCE Starch used as an adhesive in Egypt 1500 BCE Cotton cloth from India to Persia and China 1000 BCE Use of sucrose in candies, confections, and medicines in Egypt 100 CE Paper made for writing in China 700 CE Paper coated with starch paste to retain ink and provide strength Adapted from John Robyt, Essentials of Carbohydrate Chemistry 3 History of Carbohydrate Uses & Knowledge 1600 CE Sugar refineries developed in Europe 1700 CE Sugar beet developed in Europe for obtaining sucrose 1792 CE A sugar isolated from honey that was different from sucrose 1802 CE A sugar found in grapes that was also different from sucrose 1808 CE Malus developed plane polarized light and observed optical rotation by carbohydrates 1811 CE Acid-hydrolyzed starch produced a sweet crystalline sugar 1820 CE Acid-hydrolyzed cellulose also produced a sweet crystalline sugar 1821 CE Production of dextrins by heating starch: British Gums Adapted from John Robyt, Essentials of Carbohydrate Chemistry 1 4 History of Carbohydrate Uses & Knowledge 1838 CE Sugar from honey, grapes, starch, & cellulose was found to be glucose 1866 CE Kekule changed the name of glucose to dextrose because it rotates plane polarized light to the right 1870 CE Bayer and Fittig proposed the formula for glucose: HO-CH2- CH(OH)-CH(OH)-CH(OH)-CH(OH)-CHO 1874 CE Le Bel and van’t Hoff independently developed the theory of optical rotation by asymmetric tetrahedral carbon atoms with four different groups around each carbon 1881 CE A sugar was crystallized from honey that was different from sucrose and glucose, It was named levulose because it rotates plane polarized light to the left Adapted from John Robyt, Essentials of Carbohydrate Chemistry 5 History of Carbohydrate Uses & Knowledge 1886 CE Fructose, galactose, sorbose, and mannose were shown to have the same empirical formula C6H12O6 1888 CE Glucose was shown to be a six-carbon polyhydroxy aldehyde 1888 CE Fischer embarks on the determination of the structure of carbohydrates 1891 CE Fischer reports the structure of glucose, mannose, fructose, and arabinose 1892-1900 CE Controversies and discussions about intramolecular hemiacetals forming two isomeric acetals (glycosides) 1920-1930 CE The carbohydrate group led by Haworth demonstrated the size of carbohydrate rings to be primarily six-membered pyranoses and proposed a six-membered hexagon to represent carbohydrates Adapted from John Robyt, Essentials of Carbohydrate Chemistry 6 Development of Carbohydrate Nomenclature • In the early nineteenth century, individual sugars were often named after their source, e.g. grape sugar for glucose, cane sugar for saccharose (sucrose) • “Glucose” was coined in 1838; Kekulé in 1866 proposed the name “dextrose” because glucose is dextrorotatory, and the levorotatory “fruit sugar” (fructose) was for some time named “levulose” • Very early, consensus was reached that sugars should be named with the ending “-ose”, and by combination with the French word “cellule” for cell the term cellulose was coined, long before the structure was known Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 2 7 Development of Carbohydrate Nomenclature • The term “carbohydrate” (French “hydrate de carbone”) was applied originally to monosaccharides, in recognition of the fact that their empirical composition can be expressed as Cn(H2O)n. However the term is now used generically in a wider sense • Dextrorotatory (Levorotatory): Of or relating to an optically active chemical that rotates the plane of polarized light to the right (left) , or clockwise (counterclockwise) Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 8 Development of Carbohydrate Nomenclature • Emil Fischer began carbohydrate studies in 1880, assigned the relative configurations of most known sugars and had also synthesized many sugars. He and others laid the foundations of a terminology still in use, based on the terms triose, tetrose, pentose, and hexose. • The concept of stereochemistry, developed since 1874 by van't Hoff and Le Bel, had a great impact on carbohydrate chemistry. Emil Fischer introduced the classical projection formula for sugars, with a standard orientation (Fischer projection: carbon chain vertical, carbonyl group at the top). Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 9 Development of Carbohydrate Nomenclature • He assigned to the dextrorotatory glucose the projection with the OH group at C-5 pointing to the right, well knowing that there was a 50% chance that this was wrong. Much later (Bijvoet, 1951), it was proved CORRECT. • Rosanoff in 1906 selected the enantiomeric glyceraldehydes as the point of reference. Any sugar derivable by chain lengthening from what is now known as D-glyceraldehyde belongs to the D series, a convention still in use. Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 3 10 Emil Fischer (1852-1919) Fischer began his career as student of Adoph v. Baeyer *, in 1879 he became professor in München (1879), Erlangen (1881), Würzburg (1885), and Berlin (1892). In 1883 Fischer found a synthesis for indol, later he did research on purines (1880-84), on sugars, on barbituric acid, and on amino- acids. In 1902 he was awarded the Nobel Prize for chemistry, in recognition of the extraordinary services he has rendered by his work on sugar and purine syntheses. Affiliation: Berlin University * Adoph v. Baeyer was awarded Nobel Prize for Chemistry in 1905 11 Carbohydrate Definitions and Concepts Carbohydrates The generic term “carbohydrate” includes monosaccharides, oligosaccharides and polysaccharides as well as substances derived from monosaccharides by: • Reduction of the carbonyl group (alditols) • Oxidation of one or more terminal groups to carboxylic acids • Replacement of one or more hydroxy group(s) by a hydrogen atom, an amino group, or a thiol group “Carbohydrate” also includes derivatives of these compounds The term “sugar” is frequently applied to monosaccharides and lower oligosaccharides Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 12 Carbohydrate Definitions and Concepts Monosaccharides Parent monosaccharides are • Polyhydroxy aldehydes H-[CHOH]n-CHO, or • Polyhydroxy ketones H-[CHOH]n-CO-[CHOH]m-H • With three or more carbon atoms The generic term “monosaccharide” (as opposed to oligosaccharide or polysaccharide) denotes a single unit, without glycosidic connection to other such units “Monosaccharide” includes aldoses, dialdoses, aldoketoses, ketoses and diketoses, as well as deoxy sugars and amino sugars, and their derivatives, provided that the parent compound has a carbonyl group. Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 4 13 Carbohydrate Definitions and Concepts Aldoses and ketoses • Monosaccharides with an aldehydic carbonyl or potential aldehydic carbonyl group* are called aldoses • Monosaccharides with a ketonic carbonyl or potential ketonic carbonyl group* are called ketoses • * “Potential aldehydic (ketonic) carbonyl group” refers to the hemiacetal (hemiketal) group arising from ring closure Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 14 Carbohydrate Definitions and Concepts Chiral carbon atom • One of the distinguishing features of carbohydrates is that they contain one or more chiral carbon atoms • A chiral carbon atom has four different groups attaching to it • A structure containing a chiral carbon atom and its mirror image are non-superimposable CHO CHO HO H H OH OH HO L-glyceraldehyde Mirror D-glyceraldehyde 15 Carbohydrate Definitions and Concepts Fischer projection • Bonds are depicted as horizontal or vertical lines • Carbon chain is depicted vertically, (sometimes) with carbon atoms represented by center of crossing lines • C1 carbon is at the top • Horizontal bonds project forward (out of the screen) • Fischer projections depict the stereochemistry of molecule, they are very useful for differentiating stereoisomers of chiral molecules Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 5 16 Carbohydrate Definitions and Concepts Configurational atom • Monosaccharide assigned to D or L according to configuration of the highest-numbered centre of chirality, i.e. the “configurational atom”. • Hydroxy group projects to the right in the Fischer projection: D series with prefix D- • The hydroxy group projects to the left: L series with prefix L- 1 2 3 4 5 6 D-Glucose L-Glucose Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ 17 Carbohydrate Definitions and Concepts Aldoses Trivial names (with three-letter abbreviations in parentheses) and structures (in the aldehydic, acyclic form) of the aldoses with three to six carbon atoms. Only the D-forms are shown; the L-forms are the mirror images Adapted from IUPAC Nomenclature of Carbohydrates (1996) http://www.chem.qmul.ac.uk/iupac/2carb/ Carbohydrate Definitions and Concepts 18 Ketoses Structures, with systematic
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