3 Following is a Haworth projection and a chair conformation for the repeating disaccharide unit in chondroitin 6-sulfate. This biopolymer acts as the ?exible connecting matrix between the tough protein ?laments in cartilage. It is available as a dietary supplement, often combined with D-glucosamine sulfate. Some believe this combination can strengthen and improve joint ?exibility. (a) From what two monosaccharide units is the repeating disaccharide unit of chondroitin 6-sulfate derived? (b) Describe the glycosidic bond between the two units.

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Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759
BuyFind

Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759

Solutions

Chapter 20, Problem 20.83P
Textbook Problem

3 Following is a Haworth projection and a chair conformation for the repeating disaccharide unit in chondroitin 6-sulfate. This biopolymer acts as the ?exible connecting matrix between the tough protein ?laments in cartilage. It is available as a dietary supplement, often combined with D-glucosamine sulfate. Some believe this combination can strengthen and improve joint ?exibility.

Chapter 20, Problem 20.83P, 3 Following is a Haworth projection and a chair conformation for the repeating disaccharide unit in

(a) From what two monosaccharide units is the repeating disaccharide unit of chondroitin 6-sulfate derived?

(b) Describe the glycosidic bond between the two units.

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Chapter 20 Solutions

Introduction to General, Organic and Biochemistry
Ch. 20 - 1 What does it mean to say that D- and...Ch. 20 - 2 Explain the meaning of the designations D and L...Ch. 20 - 3 Which carbon of an aldopentose determines...Ch. 20 - 4 How many stereocenters are present in D-glucose?...Ch. 20 - 5 Which of the following compounds are...Ch. 20 - 6 Draw Fischer projections for L-ribose and...Ch. 20 - 7 Draw a Fischer projection for a D-2-ketoheptose.Ch. 20 - 8 Explain why all mono- and disaccharides are...Ch. 20 - .19 What is an amino sugar? Name the three amino...Ch. 20 - 0 Define the term anomeric carbon. Which carbon is...Ch. 20 - 1 Define (a) pyranose and (b) furanose.Ch. 20 - 2 Explain the conventions for using ( and ( to...Ch. 20 - 3 Are (-D-glucose and (-D-glucose anomers?...Ch. 20 - 4 Are the hydroxyl groups on carbons 1,2,3, and 4...Ch. 20 - 5 In what way are chair conformations a more...Ch. 20 - 6 Convert each of the following Haworth...Ch. 20 - 7 Convert each of the following chair...Ch. 20 - 8 Explain the phenomenon of mutarotation. How is...Ch. 20 - 9 The specific rotation of (-D-glucose is +112.2°....Ch. 20 - 0 When (-D-glucose is dissolved in water, the...Ch. 20 - 1 Define the terms glycoside and glycosidic bond.Ch. 20 - 2 What is the difference in meaning between the...Ch. 20 - Do glycosides undergo mutarotation?Ch. 20 - 4 Draw Fischer projections for the product formed...Ch. 20 - 5 Reduction of D-glucose by NaBH4 gives...Ch. 20 - 6 Reduction of D-fructose by NaBH4 gives two...Ch. 20 - 7 Ribitol and (-D-rihose 1-phosphate are...Ch. 20 - 8 Name three important disaccharides. From which...Ch. 20 - 9 What does it mean to describe a glycosidic bond...Ch. 20 - 0 Both maltose and lactose are reducing sugars,...Ch. 20 - 1 Following is a structural formula for a...Ch. 20 - 2 The disaccharide trehalose is found in young...Ch. 20 - 3 What is the difference in structure between...Ch. 20 - 4 Name three polysaccharides that are composed of...Ch. 20 - 5 Starch can be separated into two principal...Ch. 20 - 6 Where is glycogen stored in the human body?Ch. 20 - 7 Why is cellulose insoluble in water?Ch. 20 - 8 How is it possible that cows can digest grass...Ch. 20 - 9 A Fischer projection of N-acetyl-D-glucosamine...Ch. 20 - 0 Propose structural formulas for the repeating...Ch. 20 - 1 Hyaluronic acid acts as a lubricant in the...Ch. 20 - 2 The anticlotting property of heparin is partly...Ch. 20 - 3 (Chemical Connections 20A) Why does congenital...Ch. 20 - 4 (Chemical Connections 20B) What is the...Ch. 20 - 5 (Chemical Connections 20B) When L-ascorbic acid...Ch. 20 - 6 (Chemical Connections 20C) Why is the glucose...Ch. 20 - 7 (Chemical Connections 20D) What monosaccharides...Ch. 20 - 8 (Chemical Connections 20D) L-Fucose is a...Ch. 20 - 9 (Chemical Connections 20D) Why can’t a person...Ch. 20 - 0 (Chemical Connections 20E) Low-fat and...Ch. 20 - 1 2,6-Dideoxy-D-altrose, also known as...Ch. 20 - 2 In making candy or sugar syrups, sucrose is...Ch. 20 - 3 Hot-water extracts of ground willow bark are an...Ch. 20 - 4 Show how D-sorbitol, used in “sugarless” chewing...Ch. 20 - 5 Carbohydrates in most foods have roughly the...Ch. 20 - 6 Ribose and fructose have an important similarity...Ch. 20 - 7 In Section 20-4A, two structures are shown for...Ch. 20 - 8 Blood samples for research or medical tests...Ch. 20 - 9 What is the difference in the glycosidic bonds...Ch. 20 - 0 What are the structural differences between...Ch. 20 - 1 A substance called laetrile is structurally...Ch. 20 - 2 Why are five- and six-membered rings encountered...Ch. 20 - 3 What is the structural difference between...Ch. 20 - 4 Concentrated sulfuric acid can be used as a...Ch. 20 - 5 Chitin is a polysaccharide found in shrimp and...Ch. 20 - 6 In Section 20-2, we saw that in glucose, all...Ch. 20 - 7 An important part of the concern about the link...Ch. 20 - 8 Why would diabetics pay attention to the...Ch. 20 - 9 Supplements containing chondroitin sulfate are...Ch. 20 - 0 Would you expect a conformation of (-D-glucose...Ch. 20 - 1 One pathway for the metabolism of D-glucose-...Ch. 20 - 2 One step in glycolysis, the pathway that...Ch. 20 - 3 Following is a Haworth projection and a chair...Ch. 20 - 4 Below is the structural formula of coenzyme A,...Ch. 20 - 5 Vanillin (4-hydroxy-3-methoxybenzaldehyde), the...Ch. 20 - 6 The structure of the repeating disaccharide of...Ch. 20 - .87 The structure of lignin is shown below. This...Ch. 20 - 8 Most animals, including insects, cannot...Ch. 20 - 9 Paper consists primarily of cellulose fibers...

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