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Ch 8 - Problems

Ch 8 - Problems

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Published by Khris Griffis

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Published by: Khris Griffis on Apr 17, 2010
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02/20/2014

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1.
How many stereoisomers are possible for (a) a ketopentose, (b) a ketohexose, and (c) a ketoheptose?
Answer:
(a) 4; (b) 8; (c) 16.
2.
Which of the following pairs of sugars are epimers of each other?
(a)
D
-sorbose and
D
-psicose
(b)
D
-sorbose and
D
-fructose
(c)
D
-fructose and
L
-fructose
(d)
D
-arabinose and
D
-ribose
(e)
D
-ribose and
D
-ribulose
Answer:
(a) and (d)
3.
The sucrose substitute tagatose (Fig. 8-2) is produced by hydrolyzing lactose and then chemicallyconverting one of the two resulting aldoses to a ketose. Which residue of lactose gives rise to tagatose?
Answer:
Tagatose is derived from galactose.
4.
Draw the furanose and pyranose forms of 
D
-ribose.
Answer:5.
Are (a)
D
-glucitol, (b)
D
-galactitol, and (c)
D
-glycerol optically active?
Answer:
(a) Yes; (b) no (its symmetric halves are superimposable); (c) no.
6.
Draw a Fischer projection of 
L
-fucose.
L
-Fucose is the 6-deoxy form of which
L
-hexose?
Answer:
Problemshttp://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c08/dm9ld...1 of 44/17/2010 9:13 AM
 
L
-Fucose is the 6-deoxy form of 
L
-galactose.
7.
(a) Deduce the structure of the disaccharide trehalose from the following information: Completehydrolysis yields only
D
-glucose; it is hydrolyzed by
α
-glucosidase but not
β
-glucosidase; and it does notreduce Cu
2+
to Cu
+
. (b) When exposed to dehydrating conditions, many plants and invertebratessynthesize large amounts of trehalose, which enables them to survive prolonged desiccation. What properties of the trehalose molecule might allow it to act as a water substitute?
Answer:(a)
α
-D-glucose-(1
1)-
α
-d-glucose or 
α
-d-glucose-(1
1)-
β
-d-glucose.
(b)
The numerous hydrogen-bonding —OH groups of the disaccharide act as substitutes for water molecules.
8.
How many different disaccharides of 
D
-glucopyranose are possible?
Answer:
19
9.
The artificial sweetener sucralose is a derivative of sucrose with the formal name 1,6-dichloro-1,6-dideoxy-
β
-
D
-fructofuranosyl-4-chloro-4-deoxy-
α
-
D
-galactopyranoside. Draw its structure.
Answer:10.
How many reducing ends are in a molecule of glycogen that contains 10,000 residues with a branchevery 10 residues?
Answer:
One
11.
Is amylose or amylopectin more likely to be a long-term storage polysaccharide in plants?
Answer:
Problemshttp://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c08/dm9ld...2 of 44/17/2010 9:13 AM
 
Amylose (it has only one nonreducing end from which glucose can be mobilized).
12.
“Nutraceuticals” are products that are believed to have some beneficial effect but are not strictly definedas either food or drug. Why might an individual suffering from osteoarthritis be tempted to consume thenutraceutical glucosamine?
Answer:
Glucosamine is a building block of certain glycosaminoglycan components of proteoglycans (Fig. 8-12).Boosting the body's supply of glucosamine might slow the progression of the disease osteoarthritis, whichis characterized by the degradation of proteoglycan-rich articular (relating to a joint) cartilage.
13.
Calculate the net charge of a chondroitin-4-sulfate molecule containing 100 disaccharide units.
Answer:
 –200
14.
The core of pectin molecules is a polymer of 
α
(1
4)-linked
D
-galacturonate. Draw one of its residues.
Answer:15.
Draw the structure of the O-type oligosaccharide (the H antigen, described in Table 8-1).
Answer:16.
Glycogen is treated with dimethyl sulfate, which adds a methyl group to every free OH group. Next, themolecule is hydrolyzed to break all the glycosidic bonds between glucose residues. The reaction productsare then chemically analyzed.
(a)
How many different types of methylated glucose molecules are obtained?
Problemshttp://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c08/dm9ld...3 of 44/17/2010 9:13 AM

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