Problems http://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c08/dm9ld...

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 chemically
converting 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:

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Problems http://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c08/dm9ld...

L-Fucose is the 6-deoxy form of L-galactose.

7. (a) Deduce the structure of the disaccharide trehalose from the following information: Complete
hydrolysis yields only D-glucose; it is hydrolyzed by α-glucosidase but not β-glucosidase; and it does not
reduce Cu2+ to Cu+. (b) When exposed to dehydrating conditions, many plants and invertebrates
synthesize 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 branch
every 10 residues?

Answer:

One
11. Is amylose or amylopectin more likely to be a long-term storage polysaccharide in plants?

Answer:

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Problems http://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c08/dm9ld...

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 defined
as either food or drug. Why might an individual suffering from osteoarthritis be tempted to consume the
nutraceutical 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, which
is 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, the
molecule is hydrolyzed to break all the glycosidic bonds between glucose residues. The reaction products
are then chemically analyzed.

(a) How many different types of methylated glucose molecules are obtained?

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(b) Draw the structure of the one that is most abundant.

Answer:

(a) There are four types of methylated glucose molecules, corresponding to (1) the residue at the
reducing end of the glycogen molecule, (2) residues at the nonreducing ends, (3) residues at the
α(l → 6) branch points, and (4) residues from the linear α(l → 4)-linked segments of glycogen.
Type 4 is the most abundant type of residue.
(b)

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