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Major concepts
A carbohydrate can exist in the straight chain form or the cyclic form
The cyclic form of a carbohydrate comes from formation of a hemiacetal
The Haworth projection and the chair conformations are two conventions used to draw cyclic
carbohydrates
Cyclic carbohydrates can exist in two anomeric forms
Disaccharides form through glycosidic bond formation, which is an acetal
Vocabulary
Haworth projection
Chair Conformation
Anomeric carbon
D-sugar
Students should be able to:
Convert between Haworth projections and chair structures of carbohydrates
Number carbons in a cyclic carbohydrate
Recognize alpha and beta anomers of monosaccharides
Identify glycosidic linkages in disaccharides and polysaccharides
Draw Haworth projections of disaccharides given information about their glycosidic linkage
Daily Problems
4. Two glucose molecules can be linked together through a glycosidic bond to make a disaccharide. An
organic chemist recognizes that a glycosidic bond is just another name for an acetal. The glycosidic
bond can be classified by the direction of the bond made—if the bond is “down,” it is labeled an -
glycosidic bond; if it is “up,” it is labeled a -glycosidic bond. Most disaccharides also contain a
hemiacetal, and the direction of the hemiacetal OH group determines which “anomer” the disaccharide
is: the anomer has its hemiacetal hydroxyl group “down” and the anomer has its hemiacetal
hydroxyl group “up.”
H OH
4 H O
HO H H OH
2 1
HO 3
H OH 4 H O
H O 2
3 1
HO OH
H OH
H H
A. When two glucose molecules are joined with a glycosidic bond like the one shown above, the
disaccharide is called maltose. What type of glycosidic bond is found in maltose?
α-glycosidic bond
B. Which anomer of maltose is shown above?
α (14) linkage
5. Cellobiose is a disaccharide very much like maltose, except it has a (14) glycosidic linkage. Draw
the structure of the alpha anomer of cellobiose, using maltose from problem 4 as a guide. Then draw
the beta anomer of cellobiose.
H OH
H O
O H
H OH starch
HO
H OH H O
H O H OH
HO H
H OH
H O
H O
HO O
H OH
cellulose
H H
H OH
H OH
H O H OH
H O
O
O H O
HO
H OH HO O
H OH HO O
H H H OH
H H
H H
Starch and other polysaccharides that we can digest have α glycosidic linkage while cellulose has
glycosidic linkage.
7. Glucose can exist in the straight chain form, but because it contains both hydroxyl groups and an
aldehyde, it often cyclizes on itself to form a hemiacetal. On the ring structures, add numbers to the
carbons that match the numbers on the straight chain compound.
6 5 4 6
5
1
4 1
3 2
3 2
8. Draw a mechanism for formation of the six-member cyclic glucose under acid catalysis. (Hint: what
functional group is formed?)
hemiacetal