Concept explainers
(a)
Interpretation:
The two monosaccharide units from which the repeating disaccharide unit of chondroitin
Concept Introduction:
The covalent bond which is formed by the removal of water molecule from two molecules of sugar or between one molecule of sugar and an alcohol is known as a glycosidic linkage. The compounds containing glycosidic linkage are known as glycosides.
(b)
Interpretation:
The glycosidic bond formed between the two monosaccharide units is to be described.
Concept Introduction:
The covalent bond which is formed by the removal of water molecule from two molecules of sugar or between one molecule of sugar and an alcohol is known as a glycosidic linkage. The compounds containing glycosidic linkage are known as glycosides.
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Chapter 20 Solutions
Introduction to General, Organic and Biochemistry
- a) Draw Haworth projections of both - and -anomers of D-fructose. Indicate which carbon is the anomeric carbon.b) Sucrose is a disaccharide made up of a molecule of D-fructose and D-glucose. Draw the structure of sucrose clearly indicating the linkage between the two monosaccharides and its biological significance.c) Tollen’s reagent is a very mild oxidizing agent which normally oxidize aldehydes but not ketones. However, both glucose and fructose give positive results with Tollen’s reagent and are classified as reducing sugars. Explain how fructose can also give positive results with Tollen’s reagent (illustrate using structures).arrow_forwardThe disaccharide α,β-trehalose differs from the α, β structure in Figure )by having an (α1→ β1) linkage. Draw its structure as a Haworth projection.arrow_forwardDraw a Hayworth projection for the disaccharide gentibiose given that the anomeric carbon not involved in the glyosidic linkage is in a configurationarrow_forward
- The anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forwardRaffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose doesnot reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinosegives d-glucose, d-fructose, and d-galactose. When raffinose is treated with invertase,the products are d-fructose and a reducing disaccharide called melibiose. Raffinose isunaffected by treatment with a b@galactosidase, but an a@galactosidase hydrolyzes itto d-galactose and sucrose. When raffinose is treated with dimethyl sulfate and basefollowed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetraO-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the completestructures of raffinose and melibiose, and give a systematic name for melibiose.arrow_forwardConsider the tetrasaccharide stachyose drawn below. Stachyose isfound in white jasmine, soybeans, and lentils. Because humans cannotdigest it, its consumption causes flatulence. Is stachyose a reducing sugar?arrow_forward
- Consider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine, soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence.a. Label all glycoside bonds.b. Classify each glycosidic linkage as αα or ββ and use numbers to designate its location between two rings (e.g., 1→→4-ββ)-c. What products are formed when stachyose is hydrolyzed with H33O++?d. Is stachyose a reducing sugar?e. What product is formed when stachyose is treated with excess CH33I, Ag22O?f. What products are formed when the product in (e) is treated with H33O++?arrow_forward1 Draw D- glucose in a Fischer Projection. 2 Draw alpha-D- glucose and in the Hayworth (ring ) structure. 3 Draw the hydrolysis of maltose- the disaccharide composed of alpha D glucose molecules. 4 What is the chemical difference between cellulose and amylose NOTE- please dont explain too much explain to the pointarrow_forwardAn unknown reducing disaccharide is found to be unaffected by invertase enzymes. Treatment with an a@galactosidasecleaves the disaccharide to give one molecule of d-fructose and one molecule of d-galactose. When the disaccharideis treated with excess iodomethane and silver oxide and then hydrolyzed in dilute acid, the products are2,3,4,6-tetra-O-methylgalactose and 1,3,4-tri-O-methylfructose. Propose a structure for this disaccharide, and give itscomplete systematic name.arrow_forward
- Consider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine, soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence.a. Label all glycoside bonds.b. Classify each glycosidic linkage as α or β and use numbers to designate its location between two rings (e.g., 1→4-β).c. What products are formed when stachyose is hydrolyzed with H3O+?d. Is stachyose a reducing sugar?e. What product is formed when stachyose is treated with excess CH3I, Ag2O?f. What products are formed when the product in (e) is treated with H3O+?arrow_forwardDraw a chair conformation for the b-anomer of a disaccharide in which two units of d-glucopyranose are joined by an a-1,6-glycosidic bond.arrow_forwardConsider the tetrasaccharide stachyose drawn below. Stachyose isfound in white jasmine, soybeans, and lentils. Because humans cannotdigest it, its consumption causes flatulence. Label all glycoside bonds.arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning