CHEMICAL PROPERTIES OF

CARBOHYDRATES
Reducing action of sugars in alkaline
solution:
All sugars that have a free sugar group
undergoes enolization when placed in
alkaline solution
Enediols of sugar are highly reactive
and are easily oxidized by oxygen and
other oxidizing agents

Aldose-Ketose interconversion via

an enediol intermediate

 Hence enediols reduces oxidizing ions

such as Ag+, Cu++, Hg+, Fe(CN)63+
This property is utilized for
quantitative and qualitative
determinations of sugars. eg,
Benedicts solution, Fehlings solution
Cu++ reagents are the most commonly
used (Cu++ is changed to Cu+ which
forms brick red copper (I) oxide

 Oxidation to produce sugar

acids
When sugars are oxidized
under different conditions,
aldoses may produce:
Monobasic aldonic acids
Dibasic saccharic acids
Monobasic uronic acids containing
aldehyde groups thus possessing
reducing properties

 Formation of uronic acids

Occurs when the primary alcohol is
oxidized and converted to COOH group
without oxidation of an aldehyde group
D-glucose to D-glucuronic acid
D-galactose to D-galacturonic acid

 D-glucuronic acid is formed in the liver by

uronic acid pathway, an alternative
pathway for glucose oxidation.
It is a constituent of certain
mucopolysaccharides.
It also conjugates toxic substances,
drugs, hormones, and bilirubin
converting them into a non-toxic
substance glucuronide that is excreted

 Other properties of sugar

Interconversion of sugars through
enediols (glucose, fructose and
mannose)
Reduction of sugar to form sugar
alcohols
D-glucose yields D-sorbitol
D-mannose yields D-mannitol
Reaction with Iodo compounds to
iodohexanes

Other monosacharide derivatives

of biomedical importance
Deoxy sugars: sugars in which the Oxygen
of a OH group has been removed leaving
the hydrogen. Examples are:
2-deoxy-D-ribose found in DNA
6-deoxy-L-galactose found as a
constituent of glycoproteins, blood group
substances and bacterial polysaccharides

Amino sugars (Hexosamines):

These are sugars containing an NH2 group
in their structure:
Glycosylamine: the anomeric OH group
is replaced by an amino group, eg
ribosylamine which is involved in
synthesis of purines
Glycosamine: any other OH group is
replaced by amino group, eg glucosamine
and galactosamine:

 Other sugar derivatives are

amino sugar acids eg; muramic acid,
Neuraminic acids
Glycosides

DISACCHARIDES
Disaccharides are two monomers linked
together by a glycosidic bond
A glycoside is an acetal (C-O-C-O-C) at the
anomeric carbon
For Example
Maltose it is (1-4) glycosidic link
Lactose it is (1-4) glycosidic link
Sucrose it is (1-2) glycosidic link

 The reaction of formation of dissacharides

is condensation reaction and is reversible
Hydrolysis by hot acids or corresponding
enzymes yields monosaccharides
The properties of dissacharides depends
greatly on the type of linkage

Reducing ability of disaccharides

Some disaccharides such as Maltose,
Lactose are reducing sugars while
Sucrose and Trehalose are non-reducing
sugars.
This is due to the fact that there is no
free aldehyde or keto groups in sucrose
(the glycosidic bond is alpha 1-2)

Lactose Intolerance
In the intestine lactase hydrolyzes
lactose to galactose and glucose by
cleaving a 1,4-galactosidic bond
Approximately one in 4 adults is
deficient in this enzyme leading to
lactose intolerance

 Up to 90% of Asians and Africans may

be lactase-deficient as adults
Lactose accumulates in the intestine
due to poor absorption

 Bacteria metabolizes lactose producing a

lot of gasses
Also unabsorbed lactose leads to fluid
influx into the intestine
Clinical symptoms include abdominal
distension, nausea, cramping and watery
diarrhea

Classification
3 major types
Primary lactose intolerance
Environmentally induced when weaning in
non-dairy consuming societies
This is found in many Asian and African
cultures, where industrialized and
commercial dairy products are uncommon

Secondary lactose intolerance

Environmentally induced, resulting from
certain gastrointestinal diseases, including
exposure to intestinal parasites such as
giardia.
Production of lactase may be permanently
disrupted in these cases.
Commonest cause of temporary lactose
intolerance is gastroenteritis, particularly
when the gastroenteritis is caused by
rotavirus.

Congenital lactase deficiency

A genetic disorder which prevents
enzymatic production of lactase.
Present at birth, and diagnosed in early
infancy.
Management includes removal of Lactose
from the diet of these patients