Pratt and Cornely, Chapter 11

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Presentation transcript:

Pratt and Cornely, Chapter 11 Carbohydrates Pratt and Cornely, Chapter 11

Objectives Recognize and draw particular carbohydrate structures Know general structural elements of straight chain and cyclic monosaccharides Draw and name disaccharides Understand structure/function relationships of polysaccharides Predict the products of glycoside formation and breakdown

Straight-chain Monosaccarides Aldose/ketose terminology Triose, tetrose, pentose, hexose Recognize isomerization Review mechanism from chapter 6

Stereochemistry D/L designation Fisher Projections Problem 6: How many stereoisomers are possible for a ketopentose, ketohexose, and ketoheptose?

Aldose Tree Epimers

Ketose Tree

Structures to Know Dihydroxyacetone D-glyceraldehyde D-ribose D-glucose D-galactose D-fructose D-mannose

Cyclic Monosaccharides Pyranose Haworth Projection Anomeric carbon Alpha and beta anomers

Problem 14 Draw the mechanism of a cyclization reaction of D-galactose and draw the 2 possible products.

Mutarotase Reaction of cyclic carbohydrates which equilibrates anomers

Cyclic Monosaccharides Furanose Just focus on what is commonly observed Pyranoses: glucose, galactose Furanoses: ribose, fructose X

Conformations Haworth and chair (no envelopes, etc)

Derivatives: Sugar Phosphates

Other Derivatives Problems 27-28: Draw these products: a. gluconate (oxidation product of the aldehyde of glucose; b. sorbitol (reduction product of glucose)

Structure of Disaccharides Condensation of Monosacharides Loss of anomeric hydroxyl group and proton of nucleophilic alcohol Glycosidic Bond

Structure of Disaccharides Nomenclature of linkage Find the acetal! Number and linkage Reducing sugar Find the hemiacetal! Lactose

Sucrose Non-reducing sugar No hemiacetal Notice that fructose is upside down

Polysaccharides

Starch and Glycogen Compact storage

Cellulose Watch structure carefully! Function: structural support

Glycoproteins Protection and Recognition N-linked—Asn Processed Glycosidases, glycotransferase O-linked—Ser, Thr Very large (80% of mass)

Blood types Genes for different glycosyltransferases Blood type: difference in antigen on surface of red blood cells Transfusions

Congenital Disorders of Glycosylation Lysozyme digestive enzymes are marked for delivery by mannose-6-P A lectin (protein that selectively recognizes a glycan) on the lysozyme surface directs delivery If not phosphorylated, enzymes sent to wrong place and therefore… Lysozymes cannot degrade glycosaminoglycan… Buildup leads to skeletal and psychomotor retardation

Proteoglycan Mostly carbohydrate Highly charged Acts as sponge in joints

Peptidoglycan Bacterial cell wall Target for penicillin