MONOSACCHARIDE DERIVATIVES

Lesson 7

Introduction

There are important monosaccharide derivatives which are structural components of

polysaccharides. The following are the monosaccharide derivatives of importance.
1. SUGAR ALCOHOL- the aldehydic carbon is change to CH2OH. In naming this, the
“ose” is changed to “itol”

2. SUGAR AMINES – The OH in C 2 is change to NH2. In naming change “e” to amine

3. N-ACETYL SUGAR AMINE–the OH of carbon 2 is change to

NH-C=O-CH3. Naming them is similar to sugar amines but add the word N-acetyl.

4. SUGAR PHOSPHATE – OH is change to a phosphate group. It may be in any of the

carbons.

5. SUGAR ACID– maybe of 3 types. In naming them always indicate the number where the
phosphate group is attached.
a. ALDARIC ACID– Both the aldehydic carbon and the primary alcohol is
oxidized and changed to COOH.

b. ALDONIC ACID– only the aldehydic Carbon is oxidized and changed to

COOH.

c. URONIC ACID– only the primary alcohol is oxidized and changed to COOH
6. SUGAR SULFATE – OH is changed to a sulfate group in any carbon. Naming is similar to
sugar phosphate.

Objectives

At the end of the session you can:

1. Name and draw structures of monosaccharide derivatives.
2. Identify monosaccharide derivatives present in important polysaccharides
 Try this!

Using glucose as your monosaccharide, draw and name all 6 monosaccharide derivatives.

Monosaccharide structure Name

derivative
Sugar alcohol

D – Glucitol

Sugar amine

D – Glucosamine

N-acetyl sugar
amine

N – Acetyl – D –
glucosamine
Sugar acid
Aldaric acid

D – Glucaric acid

Aldonic acid

D – Gluconic acid

Uronic acid

D – Glucuronic acid

Sugar phosphate

 – D – Glucose 1 –
phosphate

Sugar sulfate

 – D – Glucose 1 –
S sulfate

Feedback: Check your answers with the instructor. If you got 70-80% correct, that’s
Great. If not, lets us move on and learn more.
 Think ahead!

You have seen especial features of the monosaccharide derivatives.

Draw the structure of the ff:

1. Xylose when converted to xylitol is used as sugar substitute in sugar free chewing gums,
mints, and other candies. As medicine it is used to prevent middle ear infections and can
prevent tooth decay and dry mouth.
2. Galactose when completely oxidized forms an insoluble white sandy crystals called
galactaric acid.
3. In glycolysis, one of the intermediate product is the formation of fructose 1,6 diphosphate
which splits to 2 trioses.

1. Xylitol

2. Galactaric Acid

3. Fructose 1,6 diphosphate

 Feedback: Check your answer with the instructor. If you answered them correctly
GOOD! If not its okey just try again.

Read and Ponder

Some important compounds whose structures are composed of these

monosaccharide derivatives.

1. Chitin - It is a long chain polymer made up of N-acetyl-D-glucosamine having a beta

1,4 link. It is the structural component in exoskeleton of insects, spider and crustaceans.
It is also the component of the cell walls of many algae and fungi . It is useful for several
medicinal, industrial and biotechnological purposes.
It is found to promote wound healing and efforts are made to construct suture
material from it.
Removal of the acetyl group from chitin yields CHITOSAN a compound used
in bandages, burn dressings, food additives drug capsules and cosmetics.

2. Hyaluronicacid - Most abundant mucopolysaccharide in the body. Acts as a lubricant

and shock absorber in the synovial fluid. It makes extra cellular matrix loose because of
its ability to attract water.
It is a linear polysaccharide made up of D-glucuronicacid and N-acetyl-D-
glucosamine residue alternately. It has a beta 1,3 and beta 1,4 link alternately.
 3. Chondroitin sulfate - It isa linear polymer made up alternately of D-glucuronicacid and
N-acetylgalactosamine residue where some OH have reacted to form sulfate esters.
Chondroitin sulfate is an important structural component of cartilage and provides
much of its resistance to compression. Common in the ground substance of connective
tissues and along with the protein collagen are used to make artificial skin which is
sometimes used as treatment of burns.
In dietary supplement used as an alternative medicine in the treatment of osteoarthritis
and has a weak anticoagulant property..

4. Heparin is a highly sulfated linear polysaccharide that was discovered in 1916 as an

anticoagulant and has been used clinically since 1935 It has no exact structure but is
said to contain sulfated glucuronic acid and glucosamine residue.

5. Pectin acts as an emulsiier, gelling agent, thickening agent, antidiarrheal formulations

and plasma substitute. Contains D-galacturonic acid + methylalcohol + galactose and
arabinose. It can be found in lemon, orange ,guava, papaya, mangoes.
 6. Agar – also called vegetable gelatin. Its chemical component are agarose which is the
gel strenght of agar and agaropectin whuch provides viscosity of the agar.
It isused as a laxative, good emulsifyingagent, preparation of jellies and
preparation of suppositories.

7. Blood type- The biochemical basis for various blood type involves monosaccharides.
There are 4 monosaccharides involve as biochemical markers. These are the D-
galactose, N-acetyl glucosamine, N-acetyl galactosamine and L-fucose (6-deoxy-L-
galactose). The arrangement of these monosaccharides as biochemical markers
determine the type of blood. Only the α –L-fucose is common to all 4 blood types. Type
A markers differ from the type O markers in that an N-acetyl galactosamine unit is also
present In type B a second galactose unit is present. The type AB blood contains both
the type A and type B markers. Type O is the universal donor while type AB is the
universal acceptor. Meaning type O can accept only from Otype while type AB can
accept bloodfrom all groups.Type A can accept only from Type A and O and Type B
can acceopt blood from type B and O.

See if you can do this!

Given above are important polysaccharides whose components are monosaccharide derivatives.
Can you identify the type of derivatives present in each.

Polysaccharide Monosaccharide derivatives

1. Chitin N – Acetyl – D – glucosamine
2. Hyaluronic acid D – Glucuronic acid and N – Acetyl – D – glucosamine
3. Chondroitin sulphate D – Glucuronic acid and N – Acetyl – galactosamine
4. Heparin Sulfated glucuronic acid and Glucosamine
5. Pectin D – Galacturonic acid and methyl alcohol
6. agar Anhydro –  – L – galactose

Feedback: check your answer with the instructor. If you got them all correct,
congratulations! If not practice more.