Lesson 12

Question for self study

1. Di- and polysaccharides are carbohydrates composed of two or more monosaccharides linked
together by glycosidic bonds. The nomenclature of di- and polysaccharides is based on the
types and positions of the glycosidic bonds that link the monosaccharides. For example, sucrose
is a disaccharide composed of glucose and fructose linked by an α,β-1,2-glycosidic bond.
2. Reducing disaccharides have a free anomeric carbon that can reduce other compounds, such
as Benedict's or Fehling's reagent. Maltose, lactose, and cellobiose are reducing disaccharides.
Nonreducing disaccharides, such as sucrose, do not have a free anomeric carbon and therefore
cannot reduce other compounds.
3. Tautomeric converting disaccharides are those that can undergo a reversible reaction between
the keto and enol forms of the carbonyl group. For example, lactose can tautomerize to
lactulose. Disaccharides can also undergo esterification reactions, where the hydroxyl groups of
the monosaccharides react with carboxylic acids to form ester linkages. Hydrolysis is a reaction
in which a bond is broken by the addition of water. Polysaccharides can be hydrolyzed to their
constituent monosaccharides.
4. Homopolysaccharides are polysaccharides composed of a single type of monosaccharide.
Starch, glycogen, cellulose, dextran, and pectin are examples of homopolysaccharides. Starch is
composed of two homopolysaccharides, amylose and amylopectin. Amylose is a linear chain of
α-D-glucose linked by α-1,4-glycosidic bonds. Amylopectin is a branched chain of α-D-glucose
linked by α-1,4-glycosidic bonds with occasional α-1,6-glycosidic bonds. Glycogen is similar in
structure to amylopectin but has more frequent branching. Cellulose is composed of β-D-
glucose linked by β-1,4-glycosidic bonds and forms a linear, rigid structure. Dextran is a
branched chain of α-D-glucose linked by α-1,6-glycosidic bonds with occasional α-1,3-glycosidic
bonds. Pectin is a branched chain of α-D-galacturonic acid linked by α-1,4-glycosidic bonds with
occasional α-1,2-glycosidic bonds.
5. Heteropolysaccharides are polysaccharides composed of two or more types of
monosaccharides. Hyaluronic acid is a heteropolysaccharide composed of repeating units of N-
acetylglucosamine and glucuronic acid. Heparin is a heteropolysaccharide composed of
repeating units of glucosamine and uronic acid. Chondroitin sulfate is a heteropolysaccharide
composed of repeating units of N-acetylgalactosamine and glucuronic acid or iduronic acid.

7.1

1. The correct option is 1) Heparin and 4) The hyaluronic acid.

2. The correct option is 3) Cellobiose.
3. The correct option is 2) D-glucose and D-fructose.
4. The correct option is 2) A non-reducing disaccharide.

7.4
7.4

1. The reaction proving reducing properties of maltose is:

Maltose + Benedict's solution + heat → Reducing sugar (glucose) + Red precipitate

The systematic name of maltose is α-D-glucopyranosyl-(1→4)-D-glucopyranose.

Maltose can undergo cyclo-oxo-tautomerism due to the presence of an open-chain aldehyde

group in one of the glucose units.

2. Polysaccharides called homopolysaccharides are composed of a single type of

monosaccharide unit. The monosaccharide units of dextran are D-glucose units with (1→6)
bonds between them.

3. The reactions of hydrolysis of starch are:

Starch + H2O + α-amylase → Intermediate products (maltose, maltotriose, and dextrins)

Intermediate products + H2O + α-amylase → Glucose

The intermediate products are maltose, maltotriose, and dextrins.

4. The hydrolysis reaction of sucrose is:

Sucrose + H2O + acid or invertase → Glucose + Fructose

Sucrose is unable for cyclo-oxa tautomerism because both glucose and fructose units are fully
substituted at the anomeric carbon, which prevents the formation of an aldehyde group required
for the tautomeric conversion.

Question and answer

5. The structure of a-D-glucopyranosyl-(1→4)-B-D-glucose is:

α-D-Glcp-(1→4)-β-D-Glcp

The common name of this disaccharide is maltose. It can undergo cyclo-oxo-tautomerism due to
the presence of an open-chain aldehyde group in one of the glucose units.

6. The structure of -D-glucopyranosyl-(1→4)-α-D-glucose units with (1→6) bond is:

The silver mirror reaction is not possible for this compound because it lacks a free aldehyde or
ketone group required for the reduction of Tollens' reagent.

7.
a) Lactose with ethanol in the presence of HCl (gas) undergoes acetal formation to produce ethyl
lactoside.
b) Cellobiose with methyl iodide in the presence of alkali undergoes methylation at the hydroxyl
group to produce methyl cellobioside.
c) Maltose acylation with acetic anhydride undergoes acetylation at the hydroxyl group to
produce acetyl maltose.

8. The hydrolysis of fully methylated lactose is not possible because all the hydroxyl groups are
substituted with methyl groups. The hydrolysis products do not have a reducing ability.

9. The oxidation reaction of cellobiose by copper hydroxide (I) is:

2 CuOH + 2 Cellobiose + O2 → 2 CuO + 2 Cellulose + 2 H2O

10. Homopolysaccharides are macromolecules composed of repeating units of a single type of

monosaccharide or disaccharide. Amylose, amylopectin, glycogen, cellulose, and dextran are
constructed from D-glucopyranose units with (1→4) and (1→6) bonds between them. The type of
bond between D-glucopyranose residues in amylose is (1→4), in amylopectin and glycogen is
(1→4) with (1→6) branches, in cellulose is (1→4) and in dextran is