Chemistry Monosaccharides Worksheet

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Name the disaccharide that is used as a starting substrate for the
synthesis of sucralose. What chemical modifications have been
made to the starting disaccharide?
CH2OH
O
CI
OH
I
H
OH
O
H
CH2CI
O
14. Keratan sulfate is a glycosaminoglycan composed primarily of the
following repeating disaccharide unit:-Gal B(1 — 4) GlcNAc6S
B(
13)—. The acetylated sugar has a sulfate ester on C-6. Ker-
atan sulfate is found in cornea, bone, and cartilage aggregated
with other glycosaminoglycans such as chondroitin sulfate. Draw
a Haworth projection of the repeating disaccharide unit found in
keratan sulfate.
15. A number of diseases result from hereditary deficiencies in spe-
cific glycosidases. In these diseases, certain glycoproteins are in-
completely degraded and oligosaccharides accumulate in tissues.
Which of the N-linked oligosaccharides in Figure 8.35 would be
affected by deficiencies of the following enzymes?
(a) N-Acetyl–glucosaminyl asparagine amidase
(b) B-Galactosidase
(c) Sialidase
(d) Fucosidase
16. A carbohydrate-amino acid polymer that is a potent inhibitor of
influenza virus has been synthesized. The virus is thought to be
inactivated when multiple sialyl groups bind to viral surface pro-
teins. Draw the chemical structure of the carbohydrate portion of
this polymer (below, where X represents the rest of the polymer).
NeuNAc a-(2-3) Gal B-(1 — 4) Glu B-(1)-X
17. Imagine that you could take a pill containing B-glucosidase. If,
after taking this pill, you ate this textbook, what would it taste
like? Would it taste any different if you could marinate it
overnight in a solution containing B-glucosidase? Should pub-
lishers use flavored ink in order to encourage students to eat their
textbooks?
Н.
HO
H
CH2C1
OH
H
13. Draw Haworth projections for the following glycosides:
(a) Isomaltose [a-D-glucopyranosyl-(1 →6)-a-D-glucopyranose).
(b) Amygdalin, a compound in the pits of certain fruits, which
has a -CH(CN)C6H5 group attached to C-1 of B-D-
glucopyranosyl-(1 →6)-B-D-glucopyranose.
(c) The O-linked oligosaccharide in collagen (B-D-galactose at-
tached to a 5-hydroxylysine residue)

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