Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
8th Edition
ISBN: 9780134015187
Author: John E. McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher: PEARSON
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Chapter 20, Problem 20.24UKC
Interpretation Introduction
Interpretation:
The oxidized monosaccharide for the given trisaccharide with its oxidized structure has to be determined and the usage of oxidation reaction to identify the sequence of given trisaccharide has to be explained.
Concept Introduction:
The hemiacetal structure of a monosaccharide is equilibrium with open structure, the oxidizing agent attacks only to the open structure of a monosaccharide because of the presence of free carbonyl group in open form.
On oxidation, the
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Consider the following statements:
(1) The term sugar is a general designation for both monosaccharides and disaccharides.
(2) The "penultimate carbon" in a monosaccharide is used to determine D- or L-configuration.
(3) Sucrose is a reducing sugar and lactose is a nonreducing sugar.
O Two of the three statements are true.
All three statements are true.
O Only one of the statements is true.
None of the statements are true.
Raffinose is a trisaccharide and a minor constituent in sugar beets. (a) Is raffinose a reducing sugar?Explain. (b) What are the monosaccharides that compose raffinose ? (c) β - Galactosidase is an enzyme that will remove galactose residues from an oligosaccharide. What are the products of β - galactosidase treatment of raffinose ?
isomaltose is a disaccharide which can be
obtained by enzymatic hydrolysis of
amylopectin. Deduce the structure of
isomaltose from the following data:
a. The hydrolysis of 1 mole of isomaltose with
acid or alpha-glucosidase yields 2 moles of D-
glucose.
b. Isomaltose is a reducing sugar
c. Isomaltose is oxidized with bromine water
to isomaltonic acid. Insomaltonic acid
methylation followed by hydrolysis yielded
2,3,4,6-tetra-O-methyl-D-glucose and 2,3,4,5-
tetra-O-methyl-D-gluconate acid.
d. Isomaltose methylation itself followed by
hydrolysis to produce 2,3,4,6-tetra-O-methyl-
D-glucose and 2,3,4-tri-O-methyl-D-glucose.
Describe according to the four points above
Chapter 20 Solutions
Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
Ch. 20.1 - Classify the following monosaccharides as an...Ch. 20.1 - Prob. 20.2PCh. 20.2 - Prob. 20.3PCh. 20.2 - Prob. 20.4PCh. 20.2 - Prob. 20.6PCh. 20.3 - D-Talose, a constituent of certain antibiotics,...Ch. 20.3 - Prob. 20.8PCh. 20.3 - Draw the structure that completes the mutarotation...Ch. 20.4 - Prob. 20.10KCPCh. 20.4 - Prob. 20.11P
Ch. 20.4 - Prob. 20.12PCh. 20.4 - Prob. 20.13PCh. 20.4 - Prob. 20.1CIAPCh. 20.4 - Prob. 20.2CIAPCh. 20.4 - All cells in your body contain glycoproteins...Ch. 20.5 - Draw the structure of the and anomers that...Ch. 20.6 - Prob. 20.15PCh. 20.6 - Prob. 20.16PCh. 20.6 - Prob. 20.17KCPCh. 20.7 - Prob. 20.4CIAPCh. 20.7 - Prob. 20.5CIAPCh. 20.7 - Prob. 20.6CIAPCh. 20.7 - Prob. 20.7CIAPCh. 20.7 - Prob. 20.18PCh. 20.7 - Prob. 20.19PCh. 20.7 - Prob. 20.8CIAPCh. 20.7 - Prob. 20.9CIAPCh. 20.7 - Prob. 20.10CIAPCh. 20 - During the digestion of starch from potatoes, the...Ch. 20 - Prob. 20.21UKCCh. 20 - Consider the trisaccharide A, B, C shown in...Ch. 20 - Hydrolysis of both glycosidic bonds in the...Ch. 20 - Prob. 20.24UKCCh. 20 - Are one or more of the disaccharides maltose,...Ch. 20 - Prob. 20.26UKCCh. 20 - Prob. 20.27UKCCh. 20 - Prob. 20.28APCh. 20 - What is the family-name ending for a sugar?Ch. 20 - Prob. 20.30APCh. 20 - Classify the four carbohydrates (a)(d) by...Ch. 20 - Prob. 20.32APCh. 20 - How many chiral carbon atoms are there in each of...Ch. 20 - Prob. 20.34APCh. 20 - Prob. 20.35APCh. 20 - Name four important monosaccharides and tell where...Ch. 20 - Prob. 20.37APCh. 20 - Prob. 20.38APCh. 20 - What is the structural relationship between...Ch. 20 - Prob. 20.40APCh. 20 - In Section 15.6, you saw that aldehydes react with...Ch. 20 - Sucrose and D-glucose rotate plane-polarized light...Ch. 20 - Prob. 20.43APCh. 20 - Prob. 20.44APCh. 20 - Prob. 20.45APCh. 20 - What is mutarotation? Do all chiral molecules do...Ch. 20 - What are anomers, and how do the anomers of a...Ch. 20 - What is the structural difference between the ...Ch. 20 - D-Gulose, an aldohexose isomer of glucose, has the...Ch. 20 - Prob. 20.50APCh. 20 - In its open-chain form, D-altrose has the...Ch. 20 - Prob. 20.52APCh. 20 - Prob. 20.53APCh. 20 - Prob. 20.54APCh. 20 - Prob. 20.55APCh. 20 - What is the structural difference between a...Ch. 20 - What are glycosides, and how can they be formed?Ch. 20 - Prob. 20.58APCh. 20 - Prob. 20.59APCh. 20 - Give the names of three important disaccharides....Ch. 20 - Lactose and maltose are reducing disaccharides,...Ch. 20 - Amylose (a form of starch) and cellulose are both...Ch. 20 - Prob. 20.63APCh. 20 - Prob. 20.64APCh. 20 - Prob. 20.65APCh. 20 - Gentiobiose, a rare disaccharide found in saffron,...Ch. 20 - Prob. 20.67APCh. 20 - Prob. 20.68APCh. 20 - Prob. 20.69APCh. 20 - Amylopectin (a form of starch) and glycogen are...Ch. 20 - What is the physiological purpose of starch in a...Ch. 20 - Prob. 20.72APCh. 20 - Prob. 20.73APCh. 20 - Prob. 20.74CPCh. 20 - Prob. 20.75CPCh. 20 - Prob. 20.76CPCh. 20 - Prob. 20.77CPCh. 20 - Prob. 20.78CPCh. 20 - Write the open-chain structure of the only...Ch. 20 - Prob. 20.80CPCh. 20 - Prob. 20.81CPCh. 20 - When a person cannot digest galactose, its reduced...Ch. 20 - Describe the differences between mono-, di-, and...Ch. 20 - Prob. 20.84CPCh. 20 - Prob. 20.85CPCh. 20 - Many people who are lactose intolerant can eat...Ch. 20 - Prob. 20.87GPCh. 20 - Prob. 20.88GPCh. 20 - Prob. 20.89GP
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- In the monosaccharide derivatives known as sugar alcohols, the carbonyl oxygen is reduced to a hydroxyl group. For example, D-glyceraldehyde can be reduced to glycerol. However, this sugar alcohol is no longer designated D or L. Why?arrow_forwardAn oligosaccharide is a repeating unit of a-D-galactopyranosyl-(a-1 >3)-allopyranoside. Each disaccharide unit is linked via B-1 --->4 glycosidic bond. The oligosaccharide has 10 monosaccharide residues. Required: Is this oligosaccharide a good substrate for glycolysis? Why or why not? Provide two reasons and discuss corn prehensively.arrow_forwardName the three digestible disaccharides we talked about. What monosaccharides are they each made of and tell whether they are connected by an alpha 1-4 glycosidic linkage, a 1-4 beta glycosidic linkage or a 1-5 beta glycosidic linkage.arrow_forward
- Trehalose, a disaccharide found in the blood of insects, has the following structure. What simple sugars would you obtain on hydrolysis of trehalose?arrow_forwardIn the structure in the picture, the monosaccharide units (alpha-D-galactopyranosyl and beta-D-allopyranose) are linked via alpha-1->3 glycosidic bond. Then, the formed disaccharide units are linked via beta-1->4 glycosidic bond. Then, an Oligosaccharide is formed which has 10 monosaccharide units, meaning that it contains 5 disaccharide units. Question: Is this oligosaccharide a good substrate for glycolysis? Provide two reasons for your answer.arrow_forwardLactose and maltose are reducing disaccharides, but sucrose is a nonreducing disaccharide. Explain.arrow_forward
- Naturally occurring D-glucose is one of a pair of enantiomers. Its mirror image is L-glucose. Draw the two cyclic six-membered isomers of L-glucose that differ in the configuration around C1 and indicate which is a and which is B.arrow_forwardCan you please identify the name of each of the structures of sugar and identify as reducing or nonreducing sugar of a,b,c and d? The picture is posted. One of the structures may be not identified from the usual structures of disaccharides.arrow_forwardConsider the disaccharide maltose. Снон H H OH H Он Part 1 of 2 Сн, он Н H Н Н он H Он H Он H Он Classify the glycosidic linkage as a or ẞ. Select the single best answer. α Part: 1/2 Part 2 of 2 Modify the structure of maltose to show the monosaccharide products that form from hydrolysis. You may draw the structures in any arrangement that you like, so long as they aren't touching. H CH₂OH Н -= о Он H ОН снон Н H H Н OH Н он H OH H Он хarrow_forward
- b-Galactosidase is an enzyme that hydrolyses only b(1,4)linkages of lactose. An unknown trisaccharide is convertedby b-galactosidase into maltose and galactose. Draw thestructure of the trisaccharidearrow_forwardAll sugar residues are in their D-isomeric forms. What kind of glycosidic linkage is between the first and second residues? What kind of glycosidic linkage is between the third and second residues?arrow_forwardIn order to metabolize lactose, most infants express the enzyme lactase in their intestines. What kind of glycosidic linkage does lactose have? Please draw the individual monosaccharides to explain your answer. Please explain how the monosaccharides in lactose will be used in glycolysis. Be specific.arrow_forward
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