FUND.OF GEN CHEM CHAP 1-13 W/ACCESS
16th Edition
ISBN: 9781323406038
Author: McMurry
Publisher: PEARSON C
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Chapter 20.4, Problem 20.12P
Interpretation Introduction
Interpretation:
The chiral carbons in , and has to be identified.
Concept introduction:
Chiral carbon:
Chiral carbon is the one which is bonded to four different molecules or groups.
Monosaccharides:
- Monosaccharides forms cyclic hemiacetals, the oxygen atom in the group of second last carbon (from bottom) attacks the carbonyl group of the same compound.
- The carbon atom in carbonyl group of monosaccharides is called anomeric carbon.
- Haworth projection is used to represent sugars in their cyclic hemiacetal forms.
- In Haworth projection,
- -indicates, the group of anomeric carbon and substituent on the carbon is trans to each other. -indicates, the group of anomeric carbon and substituent on the carbon is cis to each other.
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Name which, if any, of the following are epimers of d-glucose: Dmannose, D-galactose, D-ribose.
When a certain trisaccharide is completely methylated (i.e. all of the free OH groups have been converted to OCH3 groups) and then hydrolyzed (i.e. all of the glycosidic linkages have been broken) equal molar amounts of 2,3,4,6-tetra-O-methyl-D-galactose, 2,3,4-tri-O-methyl-D- mannose, and 1,2,4,6-tetra-O-methyl-D-glucose are obtained. When this same trisaccaride is treated with beta-galactosidase ( an enzyme that hydrolyzes the indicated glycosidic bond indicted by it's name) it yields D- galactose and a disaccharide. Treatment of the resulting disaccharride with alpha- mannosidase yields D-mannose and D-glucose. Draw the structure of the beta anomer of the original trisaccharide.
Which of an alpha-D-2,3-di-O-methylglucopyranose or alpha-D-2,3, 6-tri-O-methylglucopyranose represents a glucose unit in glycogen which was originally carrying an (alpha 1-->6) glycosidic bond?
Chapter 20 Solutions
FUND.OF GEN CHEM CHAP 1-13 W/ACCESS
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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- 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_forwardWhat sugar is produced by the epimerization of galactose?arrow_forwardName which, if any, of the following are epimers ofd-glucose: d-mannose, d-galactose, d-ribosearrow_forward
- What is/are the specific difference(s) between glucose and galactose? What is/are the specific difference(s) between glucose and fructose?arrow_forwardIn total, including lactose, how many heterodisaccharides of D-galactose and O-glucose are possible?arrow_forwardExplain why each of the following are reducing sugars: mannose, glucopyranose, fructofuranose, and maltose.arrow_forward
- Provide an explanation for the fact that a-D-mannose is more stable than B-D-mannose, whereas the opposite is truc for glucose.arrow_forwardThe anomer of a-D-glucopyranose is CH:OH он ÓH CH2OH он он он он CH,OH он он он он CH,OH он OH он ÓH ÇH;OH он он он онarrow_forwardMethionine is an essential amino acid that can be metabolized to homocysteine. Using the figure below, describe the R-group on homocysteine and how it differs from methionine. Include the functionality of the thiol as part of this discussion.arrow_forward
- Reduction of D-fructose with a reducing agent yields a mixture of d-sorbitol along with a second, isomeric product. What is the structure of the second product?arrow_forwardWhich of the following is the correct systematic name of the disaccharide shown? α-D-glucopyranosyl-(1→3)-β-D-galactopyranose α-D-gulopyranosyl-(1→4)-β-D-glucopyranose α-D-gulopyranosyl-(1→4)-β-D-galactopyranose α-D-glucopyranosyl-(1→3)-β-D-glucopyranosearrow_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_forward
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