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Understanding Carbohydrate Structures: Fischer and Haworth Projections Analysis

This guide focuses on the classification and structural characteristics of carbohydrates, including the differentiation of aldoses and ketoses, and the identification of monosaccharides such as D-glucose and D-galactose. It also explores the proper Haworth projection of β-D-galactopyranose and the nomenclature of disaccharides formed from glucose units. Emphasis is placed on recognizing cyclic monosaccharide structures, anomeric carbons, and the implications of glycosidic bonds in disaccharides and polysaccharides.

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Understanding Carbohydrate Structures: Fischer and Haworth Projections Analysis

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  1. Carbohydrates C483 Spring 2013

  2. 1. Examine the Fischer projection below. How is this carbohydrate classified? A) L enantiomer; aldopentose. B) L enantiomer; ketopentose. C) D enantiomer; aldohexose. D) D enantiomer; ketopentose. 2. Which is the proper Haworth projection of β-D-galactopyranose?

  3. Which statement is not true about this structure? • It is a ketose • It is a beta anomer. • It is a furanose. • It is a pentose. • 4. What is the name of the disaccharide shown below that is formed by joining two monomers of D-glucose? • A) β-D-glucopyranosyl-(1→4)-β-D-glucopyranose. • B) α-D-glucopyranosyl-(1→4)-α-D-glucopyranose. • C) β-D-glucofuranosyl-(1→4)-β-D-glucofuranose. • D) α-D-glucopyranosyl-(1→3)-β-D-glucopyranose.

  4. Objectives • Recognize 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

  5. Straight-chain Monosaccarides • Aldose/ketose terminology • Triose, tetrose, pentose, hexose • Recognize isomerization (TPI—see page 173) • Should I know the mechanism?

  6. Stereochemistry • D/L designation • Fisher Projections

  7. Aldose Tree

  8. Ketose Tree

  9. Structures to Know • D-glucose • D-glyceraldehyde • D-Ribose • D-Galactose • D-fructose • dihydroxyacetone

  10. Cyclic Monosaccharides • Pyranose • Haworth Projection • Anomeric carbon • Alpha and beta anomers

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

  12. Conformations • Haworth and chair (no envelopes, etc)

  13. Mutarotase • Reaction of cyclic carbohydrates which equilibrates anomers

  14. Section 8.4 Sugar Phosphates

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

  16. Structure of Disaccharides • Nomenclature of linkage • Find the acetal! • Reducing sugar • Find the hemiacetal! • “Lactose” • Reducing sugar • Nonreducing sugar • Linkage (number and stereochemistry)

  17. Polysaccharides

  18. Starch and Glycogen

  19. Cellulose • Watch structure carefully!

  20. Answers • B • I • D • A

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