BIOCHEM FINALS

WHAT ARE CARBOHYDRATES?

● Carbohydrates are the most abundant
biological molecules
● They are composed of C, O, H according to
the formula (C•H2O)n where n ≥ 3
● They are polyhydroxy aldehyde or
polyhydroxy ketone
● Basic carbohydrate units are
monosaccharides
● Polymers of monosaccharides units are
called polysaccharides

FUNCTIONS
1. Provide energy (B) Functional Group
2. Precursor of other biomolecules aldose: contains an aldehyde group
3. Storage - energy reserve ketose: contains a ketone group
4. Part of Nucleic Acid structure
5. Component if Cell membrane (with lipids)

CLASSIFICATION
Monosaccharide – smallest and the building block.
- contains only one unit of polyhydroxy aldehyde or
polyhydroxy ketone, they are soluble in water

Disaccharide – two monosaccharides bonded by

glycosidic bonds. They are also soluble in water

Oligosaccharide – three to ten monosaccharides.

Commonly found in conjugated biomolecules.

Polysaccharide – hundreds to 50,000 units

MONOSACCHARIDES
Monosaccharides are classified by:
(A) Number of carbon atoms

NAME FORMULA

Triose C3H6O3
Simplest Aldose & Ketose
Tetrose C4H8O4
General Formula For Aldose & Ketose
Pentose C5H10O5 Forms Of Monosaccharide
Hexose C6H12O6

Heptose C7H14O7

Octose C8H16O8
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ALDOSES

KETOSES
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Chirality:
Handedness in molecules
Most biological molecules, including carbohydrates,
exhibit the property of “handedness”

Most monosaccharides exist in two forms:

a “left(L) handed” and “right handed (D)” form
which are related in the same way as two hands that
are “mirror images” of each other

STEREOISOMERISM of MONOSACCHARIDES
According to the conventions proposed by Fischer:
● D-monosaccharide: a monosaccharide
that, when written as a Fischer projection,
has the -OH on its penultimate carbon on
the right
● L-monosaccharide: a monosaccharide
that, when written as a Fischer projection,
has the -OH on its penultimate carbon on
the left

“Chirality” (4 diff atoms/group of atom molecules-

connected in carbon atom [center])

Chiral molecules have handedness.

A trisubstituted methane molecule, such as
bromochloroiodomethane, is the simplest example of
a chiral organic molecule. An achiral molecule is a
molecule whose mirror images are superimposable.
Achiral molecules do not possess handedness
STEREOISOMERS: ENANTIOMERS AND
DIASTEREOMERS
• Enantiomers: stereoisomers that are mirror
images example: D-glucose and L-glucose are
enantiomers
• Diastereomers: stereoisomers that are not mirror
images example: D-ribose and D-xylose are
diastereomers
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• Epimers : diastereomers that differ around 1 By convention, horizontal lines represent bonds
carbon example: D-glucose and D-galactose are projecting from the plane of the paper toward the
diastereomers viewer, and vertical lines represent bonds projecting
away from the viewer.
EXAMPLE OF ENANTIOMER

CYCLIC CARBOHYDRATES
EXAMPLE OF DIASTEREOMER Monosaccharides have -OH and C=O groups in the
same molecule and exist almost entirely as five- and
six-membered rings

• anomeric carbon: the new stereocenter resulting

from cyclic formation

• anomers: carbohydrates that differ in

configuration only at their anomeric carbons

• The two anomers can freely interconvert in solution

- mutarotation

EXAMPLES OF EPIMERS
(diastereomers that differ in the configuration at a
single asymmetric Carbon atom)

FISCHER PROJECTION
A two-dimensional representation for showing HAWORTH PROJECTIONS
the configuration of tetrahedral stereocenters. Common way of writing a structural formula to
represent the cyclic structure of monosaccharides
with a simple three-dimensional perspective.
FISCHER PROJECTION
A two-dimensional representation for showing the
configuration of tetrahedral stereocenters.
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GLUCOSE VS. FRUCTOSE

COMMON MONOSACCHARIDES:

● GLUCOSE
▪ Large amounts generate energy in cells that have
Also called dextrose (D-glucose) and blood
limited oxygen supply (eyeball)
sugar
▪ Its dietary sources include starch & disaccharides,
lactose, maltose, and sucrose
▪ Found in large quantities throughout the living
world
▪ Primary fuel for living cells
▪ Preferred energy source of brain cells & cells that
have few or no mitochondria
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GALACTOSE
Necessary to synthesize lactose, glycolipids, certain
phospholipids, proteoglycans, and glycoproteins.
Readily synthesized from glucose-1-phosphate.
1. Weak oxidizing agents like Tollens and
Benedict’s Solutions oxidize the aldehyde
end to give an aldonic reaction. (Aldonic
Acid)

2. Strong oxidizing agents can oxidize both

ends of a monosaccharide at the same time
to produce aldaric acid. (Aldaric Acid)

3. In biochemical systems, enzymes can oxidize

the primary alcohol end of an aldose such as
glucose, without oxidation of the aldehyde
● FRUCTOSE group, to produce an alduronic acid.
- Also called levulose or fruit sugar (Alduronicacid)
- Found in some vegetables and honey
- The sweetest sugar, twice as sweet as
sucrose
- Sweetening agent in processed food products
- Large amounts are used in the male
reproductive tract (synthesized in the
seminal vesicles and then incorporated into
semen, the sperm use fructose as an energy
source)

REACTIONS OF MONOSACCHARIDES
5 Important Reactions of Monosaccharides :

Oxidation → Acidic Sugars

Reduction → Sugar Alcohols
Glycoside Formation
Phosphate Ester Formation
Amino Sugar Formation

These reactions will be considered with respect to

glucose; other aldoses, as well as ketoses, undergo
similar reactions. ➔ REDUCTION
The carbonyl group in a monosaccharide (either an
aldose or a ketose) is reduced to a hydroxyl group
using hydrogen as the reducing agent.

Product is the corresponding polyhydroxy alcohol,

sugar alcohol. e.g., sorbitol (glucitol)
- used as moisturizing agents in foods and cosmetics
and as a sweetening agent in chewing gum.
-major factor in the formation of cataracts due to
diabetes
➔ OXIDATION
Gives three different types of acidic sugars depending
of the type of oxidizing agent used:
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➔ GLYCOSIDE FORMATION
The cyclic forms of monosaccharides, the hemiacetals,
react with alcohols to form acetals, also called
glycosides.

A glycoside is an acetal formed from a cyclic

monosaccharide by replacement of the hemiacetal
carbon -OH group with an -OR group to form a
double ether.

Reduction - Under prescribed conditions, some sugars

reduce silver ions to free silver and copper (II) ions to
copper (I) ions. Such sugars are called reducing
sugars.
A reducing sugar will have one of the following
groups:
● an aldehyde group (glyceraldehyde)
● a hydroxy ketone group (fructose)
● a cyclic hemiacetal group (glucose and
maltose)
➔ PHOSPHATE ESTER FORMATION
The hydroxyl groups of a monosaccharide can react
with inorganic oxyacids to form inorganic esters.
Phosphate esters of various monosaccharides are
stable in aqueous solution and play important roles in
the metabolism of carbohydrates.

The Benedict, Barfoed, and Fehling Tests are based on

the formation of a brick red copper (I) oxide
precipitate as a positive result while the Tollen’s Test
is based on the formation of a silver mirror. The
Barfoed Test is more sensitive that it can distinguish a
reducing monosaccharide from a reducing
disaccharide. The sugars are oxidized to carboxylic
acid and the metal ions are reduced.

Redox Tests for Carbohydrates

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DISACCHARIDES
➔ AMINO SUGAR FORMATION
One of the Hydroxyl groups of a monosaccharide is
replaced with an amino group.
In naturally occurring amino sugars the carbon 2
hydroxyl group is replaced by an amino
group.
Amino sugars and their N-acetyl derivatives are
important building blocks of polysaccharides such as
chitin and hyaluronic acid

● MALTOSE
Also called malt sugar. An intermediate product of
starch hydrolysis. A disaccharide with an α(1,4)
glycosidic linkage between two D-glucose
molecules.

GLYCOSIDIC BOND
Glycoside: a carbohydrate in which the –OH of the
anomeric carbon is replaced by –OR
● those derived from furanoses are
● CELLOBIOSE
furanosides; those derived from
A degradation product of cellulose. Contains 2
pyranoses are pyranosides
molecules of glucose linked by a β(1,4)
● glycosidic bond: the bond from the anomeric
glycosidic bond.
carbon to the -OR group
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● LACTOSE ● BLOOD AND CARBOHYDRATES
Also called milk sugar.
A disaccharide composed of one molecule of galactose
linked through the OH group on C1 in a β-glycosidic
linkage to the OH of C4 of a molecule of glucose.

● SUCROSE.
Commonly called table sugar, cane sugar, and
beet sugar.
Produced in the leaves and stems of plants. Contain
both α,D-glucose and β,D'Fructose residues linked
through glycosidic bonds between both anomeric
carbons. A nonreducing sugar.

OLIGOSACCHARIDES
Carbohydrates that contain three to ten
monosaccharides.
Arrangement of these monosaccharide in the
oligosaccharide determines the blood type of a person.
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POLYSACCHARIDES
Structural Polysaccharide
Storage Polysaccharide ● CELLULOSE
● STARCH - a polysaccharide composed of
- the principal food reserve in plants - D-glucopyranose residues linked by
polymers of α-D- glucose units β(1,4)-glycosidic bonds
- The most important structural
AMYLOSE VS. AMYLOPECTIN polysaccharide of plants
Amylose - a straight chain polymer of D-glucose - Comprises one-third of plant biomass, hence
units. it is the most abundant organic
substance on earth
- Not digested by human beings but can be
digested by some animal species using the
enzymes called cellulase.

Amylopectin - a branched chain polymer of

D-glucose units.

RUMINANT ANIMALS

● GLYCOGEN
- storage polysaccharide in animals
- bush-like with α(1→6) branch
points
- Every 8 - 12 glucose residues for
glycogen
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Chitosan
● Made by treating the chitin shells of shrimp
and other crustaceans with an alkaline
substance

Chitin
● A polysaccharide that is like cellulose, both
in it biological function and its primary,
secondary, and tertiary structure,
● Chitin is present in the cell walls of fungi and
is the fundamental material in the
exoskeletons of crustaceans, insects, and
spiders.
● The structure of chitin, an extended ribbon,
is identical to cellulose, except that the -OH
group on each C-2 is replaced by -NHCOCH3,
so that the repeating units are
N-acetyl-D-glucosamine in β(1,4) linkage.