7 Carbohydrates

Carbohydrates
Dr Tolunimi Adedeji (MD)
I. Overview
Carbohydrates are the most abundant biomolecules

They provide a significant portion of the energy in the diet
of most organisms
They also act as a storage form of energy in the body
Carbohydrates serve as structural components of many
organisms
General formula is represented as (CH2O)n hydrate of
carbon
II. Classification and structure of

carbohydrates
The simplest carbohydrates

are monosaccharides
can be classified based on
the number of carbon
atoms
Some common
monosaccharides found in
humans (see figure)
Carbohydrates with an
aldehyde functional group
are known as aldoses
Carbohydrates that contain
a ketone moiety are called
ketoses (see examples)
II. Classification and structure of

carbohydrates
Monosaccharides, when
linked with each other, form
glycosidic bonds to generate
extended structures (see
figure)
Disaccharides consist of two
monosaccharide units
Oligosaccharides contain
from three to twelve
monosaccharide units
Polysaccharides are
comprised of more than twelve
monosaccharide units, and can
be hundreds of
monosaccharides long
A. Isomers and epimers
Isomers compounds having

the same chemical formula but
different structural formulas
Examples of isomers fructose,
glucose, mannose, galactose all
have chemical formula C6H12O6
Epimers monosaccharides
(isomers) that have different
configurations around one
specific carbon atom
Examples of epimers glucose
and galactose are C-4 epimers
(see figure)
glucose and mannose are C-2
epimers
B. Enantiomers
Enantiomers optically
active isomers that are
mirror images of each other
In monosaccharides, the two
enantiomers are each
termed a D- and L-sugar (see
figure)
The vast majority of
monosaccharides in humans
are D-sugars
C. Cyclization of monosaccharides
The open chain form of

monosaccharides exist in solution
as less than one percent abundant
The ring or cyclized form is the
more stable form, which occurs
when the aldehyde or ketone group
has reacted with an alcohol group
on the same monosaccharide
Formation of the ring also creates
an anomeric carbon at carbon 1
of an aldose and carbon 2 of a
ketose
The anomeric carbon gives rise to
two different configurations around
it - or configurations (see
figure)
Interconversion of these anomers
is called motarotation
C. Cyclization of monosaccharides
If the oxygen atom on the anomeric carbon (carbonyl

group) of a monosaccharide is not attached to any other
structure, the sugar is a reducing sugar
A reducing sugar can react with chemical reagents (e.g.
Benedicts solution) upon which the anomeric carbon is
oxidized and the chemical reagent reduced
D. Complex carbohydrates
Carbohydrates can also be linked to

non-carbohydrate structures via
glycosidic bonds (e.g. purines and
pyrimidines found in nucleic acids,
aromatic rings present in steriods,
proteins found in glycoproteins, and
lipids found in glycolipids)
The aldose or ketose unit in these
structures are called glycosyl
residues
Lactose is, therefore, known as
galactosyl-glucose, since it is
comprised of one galactose and one
glucose
If the moiety on the non-carbohydrate
molecule to which the sugar is
attached is an OH group, the
structure is an O-glycoside
If the group is an NH2, the structure
is an N-glycoside (see figure)
D. Complex carbohydrates
Glycosidic bonds between monosaccharide units are

named according to the numbers of the connected carbon
atoms, and also to the position of the anomeric hydroxyl
group of the sugar involved in the bond
If the anomeric OH group has an configuration, the
bond formed is an -bond; if the configuration is shown,
the bond is a -bond
The glycosidic bond in lactose, for instance, is formed
between carbon 1 of -galactose and carbon 4 of glucose (1 4) glycosidic bond
Lactose is also a reducing sugar
III. Digestion of carbohydrates
Carbohydrate digestion primarily

occurs in the mouth and intestinal
lumen
A mixed animal and plant diet has
little monosaccharide present
(contains disaccharides,
oligosaccharides, and polysaccharides)
Enzymes (disaccharidases and
endoglycosidases) are, therefore,
required for digestion of
carbohydrates
Carbohydrate digestion involves
hydrolysis of glycosidic bonds (see
figure)
These enzymes are usually specific for
the type of glycosyl residue and also
for the type of glycosidic bond
Digestion of carbohydrates begins in the

mouth
The principal dietary polysaccharides include
glycogen (animal derived) and starch (plant
derived, composed of amylose and
amylopectin)
During mastication, salivary -amylase breaks
some (14) bonds
Humans cannot digest cellulose, due to the
lack of (14)-endoglucosidases, which cleave
(14) bonds
After mastication, the (16) bonds present in
glycogen or starch are not broken, and smaller
branched oligosaccharides remain (see figure)
Carbohydrate digestion does not continue into
the stomach (high acidity deactivates salivary
-amylase)
When acidic stomach contents

reach the small intestine, they are
neutralized by bicarbonate secreted
by the pancreas
Pancreatic -amylase continues to
work on carbohydrate digestion
The final digestive stages occur at
the mucosal lining of the upper
jejunum, and continue into the
small intestine, where several
disaccharidases and
oligosaccharidases act on the
carbohydrate (see figure)
Isomaltase cleaves the (16)
bonds while maltase cleaves
maltose; sucrase hydrolyzes
sucrose; lactase cleaves lactose
Abnormal digestion of
carbohydrates can occur when a
defect in disaccharidase activity
of the intestinal mucosa causes
the passage of undigested
carbohydrate into the large
intestine water from the mucosa
is drawn into the large intestine,
causing osmotic diarrhea
This can also be accompanied by
bacterial fermentation of the
carbohydrate to two- and threecarbon compounds and large
amounts of CO2 and H2 gas,
which cause abdominal cramps,
diarrhea, and flatulence (see
figure)
Digestive enzyme deficiencies could also lead to improper

digestion of carbohydrates
Disaccharide intolerance has been reported in some infants
and children (hereditary)
This condition may also be manifested as a result of
malnutrition or drug use
More than one half of the worlds adults are lactose
intolerant; certain races, e.g. African or Asian descent, are
lactase deficient, compared to people of northern European
origin
Isomaltase-sucrase deficiency also present in about ten
percent of Greenlands Eskimos inability to digest sucrose
Diagnosis of an enzyme deficiency can be afforded through
oral tests, e.g. measurement of H 2S gas in breath
Key concept map for structure of

monosaccharides
Explain in your own

words
glycosidic bonds
anomeric carbon
alpha configuration
isomers
enatiomers
glycosyl residues
reducing sugars
draw a flowchart of the digestion of
carbohydrates

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Carbohydrates

Dr Tolunimi Adedeji (MD)

Carbohydrates are the most abundant biomolecules

II. Classification and structure of

The simplest carbohydrates

II. Classification and structure of

A. Isomers and epimers

Isomers compounds having

The open chain form of

If the oxygen atom on the anomeric carbon (carbonyl

Carbohydrates can also be linked to

Glycosidic bonds between monosaccharide units are

III. Digestion of carbohydrates

Carbohydrate digestion primarily

III. Digestion of carbohydrates

Digestion of carbohydrates begins in the

III. Digestion of carbohydrates

When acidic stomach contents

III. Digestion of carbohydrates

III. Digestion of carbohydrates

Digestive enzyme deficiencies could also lead to improper

Key concept map for structure of

Explain in your own

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