Carbohydrates Pratt and Cornely, Chapter 11. Objectives Recognize and draw particular carbohydrate structures Know general structural elements of cyclic.

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Presentation transcript:

Carbohydrates Pratt and Cornely, Chapter 11

Objectives Recognize and draw particular carbohydrate structures Know general structural elements of cyclic monosaccharides and disaccharides, and their implications for structure/function Predict the products of condensation reactions and hydrolysis

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 D-glucose D-glyceraldehyde D-Ribose D-Galactose D-fructose dihydroxyacetone

Cyclic Monosaccharides Pyranose Haworth Projection Anomeric carbon Alpha and beta anomers

Problem 14 Carry out a cyclization reaction with D- galactose and draw the 2 possible products.

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

Conformations Haworth and chair (no envelopes, etc)

Mutarotase Reaction of cyclic carbohydrates which equilibrates anomers

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)

Proteoglycan Mostly carbohydrate Highly charged Acts as sponge in joints

Peptidoglycan Bacterial cell wall Target for penicillin