Fucose, one of several monosaccharides found in the surface polysaccharides of animal cell membranes, is synthesized biochemically from mannose in the following eight steps. СНО -H- CH,OH CH,OH H,C H Но- H. Но- -H- ОН НО, CH3 ОН НО ОН НО НО ОН НО You H H HO- ČH,OH Mannose СНО H H H Но H- H CH, Но H НО OH CH3 Но VÓH HO H НО H- HO- НО НО H Но- H ČH3 Fucose

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter25: Biomolecules: Carbohydrates
Section25.6: Reactions Of Monosaccharides
Problem 17P
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How many stereoisomers would result from the reaction of fucose with methanol and acid catalysis?

1. Because there are four chiral centers, one would get 24 isomers.

2. One would get two isomers: the a- and b-anomers.

3. Two diastereomers would form by scrambling the stereochemistry of the carbon with a-hydrogens.

4. There would be no reaction and hence no stereoisomers would be created

Fucose, one of several monosaccharides found in the
surface polysaccharides of animal cell membranes,
is synthesized biochemically from mannose in the
following eight steps.
СНО
-H-
CH,OH
CH,OH
H,C
H
Но-
H.
Но-
-H-
ОН НО,
CH3
ОН НО
ОН НО
НО
ОН НО
You
H
H
HO-
ČH,OH
Mannose
СНО
H
H
H
Но
H-
H
CH,
Но
H
НО
OH
CH3
Но
VÓH
HO
H
НО
H-
HO-
НО
НО
H
Но-
H
ČH3
Fucose
Transcribed Image Text:Fucose, one of several monosaccharides found in the surface polysaccharides of animal cell membranes, is synthesized biochemically from mannose in the following eight steps. СНО -H- CH,OH CH,OH H,C H Но- H. Но- -H- ОН НО, CH3 ОН НО ОН НО НО ОН НО You H H HO- ČH,OH Mannose СНО H H H Но H- H CH, Но H НО OH CH3 Но VÓH HO H НО H- HO- НО НО H Но- H ČH3 Fucose
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