Chapter 7 Carbohydrates
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1 Chapter 7 Carbohydrates
2 Definition of Carbohydrates carbohydrate: hydrate of carbon ; C n ( 2 ) m Examples: glucose (C or C 6 ( 2 ) 6 ), sucrose (C or C 12 ( 2 ) 11 ) saccharide: simple sugar group monosaccharides, disaccharides, polysaccharides monosaccharides are C n 2n n
3 Functional Groups Carbohydrates can be classified as: Polyhydroxyaldehydes: many alcohols and an aldehyde Polyhydroxyketones: many alcohols and a ketone
4 Structure and Nomenclature Named by the functional group + number of carbons (keto-) or (aldo-) + (tri-, tetr-, pent-) + -ose aldotetrose C 2 C 2 ketone group aldehyde group C C C ketotriose C 2
5 Chirality Stereocenter: tetrahedral carbon with four different substituents chiral carbon or asymmetric center enantiomers same compound A X D Z Z X D A rotate A X Z D A D Z Z D A rotate A D Z reflect reflect
6 Stereocenters Br stereocenter not a stereocenter stereocenters not a stereocenter stereocenter ow many chiral carbons are in: Br Br
7 Fisher Projections Glyceraldehyde: an aldotriose stereocenter C C C 2 glyceraldehyde Fisher Projection: two-dimensional representation of stereocenters as the only atoms in plane Wedges (toward you) are horizontal Dashes (away from you) are vertical C C 2 C C 2 C C 2
8 Chirality in Carbohydrates ow many chiral carbons are present? Are these structures (1) enantiomers, (2) constitutional isomers, or (3) neither?
9 D and L Configuration Sugars are designated with D (right) and L (left). C C C C 2 C 2 D-erythrose D-glyceraldehyde L-glyceraldehyde C 2
10 D and L Configuration
11 Physical Properties Most are colorless, crystalline solids with a sweet taste (sugars). The many alcohols make the compounds extremely polar. All three intermolecular forces Very water-soluble
12 emiacetals ydroxyaldehydes will form hemiacetals. 4-hydroxypentanal redrawn hemiacetal redrawn hemiacetal 5-hydroxyhexanal Are these isomers or different compounds? ow many stereocenters are in the hydroxyaldehydes? ow many are in the hemiacetals?
13 Furanose and Pyranose The cyclic hemiacetal forms are particularly stable when forming a 5- or 6-membered ring. furan pyran Furanose: 5-membered Pyranose: 6-membered anomeric carbon: new stereocenter created in forming the cyclic hemiacetal
14 aworth Projections Left in Fisher up from ring Right in Fisher down from ring Anomeric carbon s alcohol can be either up or down.
15 aworth Projections xygen in the ring is always pointed backwards. Anomeric carbon is always to the right. All three isomers exist in in equilibrium.
16 Important Monosaccharides b-ribose b-deoxyribose b-glucose b-galactose b-fructose
17 xidation reducing sugar: carbohydrate that reacts with an oxidizing agent b-d-glucopyranose 2 C D-glucose C C 2 [] basic conditions - C 2 D-gluconate 2-ketoses are also reducing sugars. - R - - [] R R R 2-ketose enediol aldose aldonate
18 Formation of Phosphate Esters Mono- and diphosphoric esters serve as intermediates in the metabolism of monosaccharides. phosphorylation: addition of a phosphate ester C C 2 enzyme-catalyzed phosphorylation C C 2 P P - 2 C monophosphate ester
19 Formation of Acetals Recall: aldehyde or ketone + alcohol hemiacetal + benzaldehyde ethanol hemiacetal hemiacetal ethanol acetal
20 Glycosides Addition of an alcohol to a monosaccharide in acidic conditions will form a glycoside. glycoside: cyclic acetal derived from a monosaccharide b-d-glucopyranose methyl b-d-glucopyranoside 2 C + C C C 3 glycosidic bond glycosidic bond: bond between the anomeric carbon and the new R group formed during the conversion to an acetal
21 Disaccharides disaccharide: two sugar units linked through a glycosidic bond a-d-glucose b-d-fructose sucrose: a(1 2) glycosidic bond maltose: a(1 4) glycosidic bond a-d-glucose a-d-glucose lactose: b(1 4) glycosidic bond b-d-galactose a-d-glucose
22 Polysaccharides starch: polymer of D-glucose units connected with a(1 4) linkages glycogen: polymer of D-glucose units connected with a(1 4) and a(1 6) linkages cellulose: polymer of D-glucose units connected with b(1 4) linkages
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A. Incorrect! No, this is not the description of this type of molecule. B. Incorrect! No, this is not the description of this type of molecule.
Biochemistry - Problem Drill 08: Carbohydrates No. 1 of 10 1. have one aldehyde (-CHO) or one keto (-C=O) group and many hydroxyl (-OH) groups. (A) Amino acids (B) Proteins (C) Nucleic Acids (D) Carbohydrates
What are Carbohydrates? Aldoses and Ketoses
What are Carbohydrates? Polyhydroxylated aldehydes and ketones Commonly called sugars General formula of common sugars!glucose: C 6 ( 2 ) 6!Glyceraldehyde: C 3 ( 2 ) 3 Talking points: C 2 ACS Division
II. Chemistry of Sugars
II. Chemistry of Sugars Sugars-or saccharides- are the most abundant bio-molecule on the planet. They are important in a number of biological roles. Most obviously you will know them as a major component