ZieglerLecture9-Carbohydrates-ppt1

ZieglerLecture9-Carbohydrates-ppt1 - Lecture 9:...

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Lecture 9: Lecture 9: Carbohydrates Carbohydrates BIOCHEMISTRY 100 Winter 2009 M. Ziegler
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Learning Objectives Learning Objectives 1. Terminology (explain/defne; understand use oF terms): mono-, oligo-, polysaccharide, aldose, ketose, triose (etc.), chiral center (chiral C, asymmetric C), enantiomer, diasteriomer, epimer, pyranose, Furanose, hemiacetal, hemiketal, acetal, ketal, glycosidic bond, anomeric C, anomer, reducing sugar, reducing end (oF an oligo- or polysaccharide), alditol 2. Structures (all but glycogen and chitin are from “vocabulary” list) (draw F = Fischer; draw H = Haworth; R = Recognize) Drawing Haworth: Be able to draw either the α or β anomeric form. D-2-deoxyribose (H) Ribose (H) D-Glucose (F,H) Maltose (H) D-Galactose (F,H) Lactose (H) D-Fructose (H) Sucrose (H) D-Glyceraldehyde (F) Cellulose (R) β -N-Acetylgalactosamine (R) Glycogen (R) Starch (R) (amylose, amylopectin) Chitin (R)
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Learning Objectives Learning Objectives 3. Be familiar with a) oxidizing an aldose to the carboxylic acid oxidation state (relates to definition of a “reducing sugar”), and b) reducing the carbonyl C of an aldose to an alcohol. 4. Explain hemiacetal and acetal formation, and the difference between them in terms of reversibility of the reaction in neutral aqueous solution. 5. Given the structure (Fischer or Haworth) of any of the hexoses or of an oligosaccharide, decide whether or not it is a “reducing sugar”, and be able to explain why, including identifying “reducing end” and “non-reducing ends” of oligo- and polysaccharides. 6. Explain how the conformation of “storage” polysaccharides (starch or glycogen) vs. the conformation of “structural” polysaccharides (cellulose or chitin) relates to the type of linkage between monomers, α (1 4) vs. β (1 4) .
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Carbohydrates Carbohydrates (defnition) (defnition) polyhydroxyaldehydes, polyhydroxyketones, or molecules that give these compounds on hydrolysis Monosaccharide: Monosaccharide: a carbohydrate that cannot be hydrolyzed to a simpler carbohydrate general formula C n H 2n 2n O n , where n varies from 3 to 8 aldose aldose : a polyhydroxy aldehyde ketose ketose : a polyhydroxy ketone classiFcation by number of C atoms in monosaccharide:
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Monosaccharides Monosaccharides The only 2 trioses Phosphorylated derivatives of these are important structures in glycolytic pathway.
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Monosaccharides Monosaccharides Glyceraldehyde: reference compound for D-L stereoisomers contains an asymmetric C (a chiral center) Enantiomers of glyceraldehyde ( complete mirror images of each other): L-Glyceraldehyde D-Glyceraldehyde CHO C CHO C H OH CH 2 OH CH 2 OH H HO
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Fischer Projections, D and L Fischer Projections, D and L Fischer projection: Fischer projection:
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This note was uploaded on 02/25/2009 for the course BCH 100 taught by Professor Staff during the Spring '08 term at UC Riverside.

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ZieglerLecture9-Carbohydrates-ppt1 - Lecture 9:...

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