Carbohydrates

CARBOHYDRATES
Biochemistry
Mrs. Merly P. Alfafara
Reference: Biochemistry by H.S. Stoker

BIOCHEMISTRY – AN OVERVIEW
○ It is the study of the chemical substances

found in living organisms and the chemical
interactions of these substances with each
other
○ The knowledge explosion that has
occurred in this field during the last
decades of the twentieth century and the
beginning of the twenty-first century is
truly phenomenal
BIOCHEMICAL SUBSTANCE
○ It is a chemical substance found
within a living organism
○ These substances are divided into
two groups: bioinorganic
substances and bioorganic
substances
MASS COMPOSITION DATA FOR THE
HUMAN BODY
BIOCHEMICAL
SUBSTANCES
BIOINORGANIC BIOORGANIC
SUBSTANCES SUBSTANCES
Substances that do Substances that

not contain carbon contain carbon
Water Inorganic salts Protein Lipids Carbohydrates Nucleic Acids

(about 70%) (about 5%) (about 15%) (about 8%0 (about 2%) (about 2%)
BIOCHEMICAL SUBSTANCES
○ As isolated compounds, bioinorganic and
bioorganic substances have no life in and
of themselves
○ Yet when these substances are gathered
together in a cell, their chemical
interactions are able to sustain life
○ It is estimated that more than half of all
organic carbon atoms are found in the
carbohydrate materials of plants
BIOCHEMICAL SUBSTANCES
○ Human uses carbohydrates of the
plant kingdom extend beyond food
● Carbohydrates in the form of cotton and
linens are used as clothing
● Carbohydrates in the form of wood are
used for shelter and heating and in
making paper
OCCURRENCE AND FUNCTIONS OF
CARBOHYDRATES
○ Carbohydrates are the most

abundant class of bioorganic
molecules on planet Earth
○ In plants, carbohydrates constitute
about 75% by mass of dry plant
materials
CARBOHYDRATES
○ Green (chlorophyll-containing) plants produce
carbohydrates via photosynthesis
Chlorophyll
CO2 + H2O + solar energy carbohydrates + O2
Plant enzymes
○ Plants have two main uses for

carbodydrates they produce:
● Cellulose – serves as structural elements
● Starch – provide energy reserves
CARBOHYDRATES
○ Dietary intake of plant materials is

the major carbohydrate source for
humans and animals
○ The average human diet should
ideally about two-thirds
carbohydrates by mass
CARBOHYDRATES
○ Functions of Carbohydrates in Humans

● Carbohydrate oxidation provides energy
● Carbohydrate storage, glycogen, provides a
short-term energy source
● Carbohydrates supply carbon atoms for the
synthesis of other biochemical substances
● Carbohydrates form part of the structural
framework of DNA and RNA molecules
● Carbohydrates linked to lipids are structural
components of cell membranes
● Carbohydrates linked to proteins function in a
variety of cell-cell and cell-molecule recognition
process
CLASSIFICATION OF
CARBOHYDRATES
○ Most simple carbohydrates have

empirical formula that fit the general
formula CnH2nOn.
○ Early observation by scientists that
the above-mentioned formula can
also be written as Cn(H2O)n, hydrate
of water
CLASSIFICATION OF
CARBOHYDRATES
○ A carbohydrate is a polyhydroxy
aldehyde, a polyhydroxy ketone, or
a compound that yields polyhydroxy
aldehydes or polyhydroxy ketones
upon hydrolysis.
CLASSIFICATION OF
CARBOHYDRATES
H O
C CH2OH
H C OH C O
HO C H HO C H
H C OH H C OH
H C OH H C OH
CH2OH CH2OH
D-glucose D-fructose
(a polyhydroxy aldehyde) (a polyhydroxy ketone)

CLASSIFICATION OF
CARBOHYDRATES
○ Monosaccharide
● Is a carbohydrate that contains a single
polyhydroxy aldehyde or polyhydroxy
ketone unit
● Cannot be broken down into simpler
units by hydrolysis (addition of water
molecule)
● Pure monosaccharides are water-
soluble, white, crystalline solids
● Examples: Glucose and Fructose
CLASSIFICATION OF
CARBOHYDRATES
○ Oligosaccharide
● A carbohydrate that contains two-ten
monosaccharide units covalently
bonded to each other
● Disaccharide – most common type of
oligosaccharide that contains two
monosaccharide units covalently
● Example: Sucrose (table sugar)
CLASSIFICATION OF
CARBOHYDRATES
○ Polysaccharide
● A polymeric carbohydrate that contains
many monosaccharide units covalently
● Example: Cellulose, Starch
○ Upon hydrolysis, oligosaccharides

and polysaccharides produce
monosaccharide units
CHIRALITY: HANDEDNESS IN
MOLECULES
○ Handedness
● An important general structure property
of most monosaccharide
● Two forms: left-handed and right
handed (mirror images)
○ This property in not restricted to
carbohydrates
MOLECULES
○ Mirror image
● Is the reflection of an object in a mirror
● Superimposable mirror image
○ Images that coincide at all points when
the image are laid upon each other
● Nonsuperimposable mirror image
○ Images where not all points coincide when
the images are laid upon each other –
exists in “left-handed” and “right-handed”
MOLECULES
MOLECULES
○ Not all molecules possess handedness

○ Any organic molecule that contains a
carbon atom with four different groups
attached to it in a tetrahedral orientation
possesses handedness
○ Chiral Center
● An atom in a molecule that has four different
groups tetrahedrally bonded to it
MOLECULES
○ Chiral Molecule
● A molecule whose mirror images are
not superimposable
○ Achiral Molecule
● A molecule whose mirror images are
superimposable
MOLECULES
H CHO
I C Cl H C OH
Br CH2OH
Bromochloroiodomethane Glyceraldehyde
(chiral organic compound) (simple chiral monosaccharide)
MOLECULES
CH3
H3C CH2 CH2 * C CH2 CH3
H
H 3-Methylhexane
*
H3C CH2 C CH3
Cl
OH *
H C CH3
2-Butanol
I
1-Chloro-1-iodoethane
EXERCISES
Indicate whether the circled carbon atom in each of the following
molecules is a chiral center.
H
H3C CH2 C CH3 H3C CH2 C CH3
Cl O
H
Br
H3C CH2 C CH3
CH
CH2 H2C CH2
CH CH2
CH3 Br CH2
MOLECULES
○ Organic molecules, especially

monosaccharides, may contain more than
one chiral center
O
CHO
H3C CHO meansH3C C
H *C OH H
H *C OH H
CH2OH H3C CH2OH meansH3C C OH

H
Naturally occurring monosaccharides are almost always “right-handed”.
STEREOISOMERISM: ENANTIOMERS
AND DIASTEREOMERS
○ Stereoisomers
● Are isomeric molecules that have the
same molecular formula and sequence
of bonded atoms but differ in three-
dimensional orientation of their atoms
in space
AND DIASTEREOMERS
○ Features that generate

stereisomerism:
● Presence of a chiral center in a molecule
● Presence of “structural rigidity” in a
molecule
AND DIASTEREOMERS
○ Enantionamers
● Are stereoisomers whose molecules are
nonsuperimposable mirror images of
each other
● Left- and right-handed forms of a
molecule with a single chiral center are
enantiomers
● Came from the Greek word enantios,
meaning opposite
AND DIASTEREOMERS
○ Diastereomers
● Are stereoisomers whose molecules are
not mirror images of each other
● Examples: Cis-trans isomers of alkenes
and cycloalkanes
● Molecules that contain more than one
chiral center can also exist in
diastereomeric as well as enantiomeric
forms
AND DIASTEREOMERS
CHO CHO CHO CHO

H C OH HO C H H C OH H C OH
H C OH HO C H HO C H H C OH
H C OH HO C H H C OH HO C H
CH2OH CH2OH CH2OH CH2OH
Enantiomers Diastereomers
AND DIASTEREOMERS
No Do the molecules have the same molecular formula? Yes
The molecules
The molecules are are ISOMERS.
NOT isomers.
Are the atoms bonded in the

No same order in the two
molecules?
The molecules are Yes
STEREOISOMERS.
The molecules are
CONSTITUTIONAL
ISOMERS.
Are the molecules
Yes NONSUPERIMPOSABLE No
MIRROR IMAGES?
The molecules are ENANTIOMERS. The molecules are DIASTEREOMERS.

DESIGNATING HANDEDNESS USING
FISCHER PROJECTION FORMULAS
○ It is a two-dimensional structural notation

for showing the spatial arrangement of
groups about chiral centers in molecules
○ Chiral center is represented as the
intersection of vertical and horizontal lines
○ The chiral center, which is almost always
carbon, is not explicitly shown
CH3
chiral center
H CH3
I
○ Example: Glyceraldehyde
O
*
H2C CH C H
OH OH
CHO CHO
HO H H OH
CH2OH CH2OH
L-Glyceraldehyde D-Glyceraldehyde
D- (dextro) means right and L- (levo) means left.

There are four stereoisomers for the compound below – two
pairs of enantiomers.
* *
H2C HC CH C H
OH OH OH O
CHO CHO CHO CHO
H OH HO H HO H H OH
H OH HO H H OH HO H
First enantiomeric pair Second enantiomeric pair

In a monosaccharide with more than one chiral carbon:
1. The carbon chain is numbered starting at the carbonyl
group of the molecule
2. The last chiral carbon is used to determine D or L
configuration
CHO CHO CHO CHO

H OH HO H HO H H OH
H OH HO H H OH HO H
D-isomer (A) L-isomer (B) D-isomer (C) L-isomer (D)

D-Erythrose L-Erythrose D-Threose L-Threose
○ As Diastereomers
● A and C
● A and D
● B and C
● B and D
○ Each of these pairs are epimers –
diastereomers whose molecules
differ only in the configuration at
one chiral center
EXERCISES
Draw a Fischer projection formula for the enantiomer of each of
the following monosaccharide.
CHO CH2OH
H C OH C O
H C OH HO C H
H C OH H C OH
CH2OH CH2OH
A polyhydroxy aldehyde A polyhydroxy ketone
ANSWERS
CHO CHO CH2OH CH2OH

H C OH HO C H C O C O
H C OH HO C H HO C H H C OH
H C OH HO C H H C OH HO C H
EXERCISES
Classify each of the following monosaccharides as D or an L
enantiomer.
CHO CH2OH
HO C H C O
HO C H HO C H
HO C H H C OH
CH2OH CH2OH
L-isomer D-isomer
ISOMERISM
PROPERTIES OF ENANTIOMERS
○ When plane-polarized light is passed

through a solution containing a single
enantiomer, the plane of the polarized
light is rotated counterclockwise (to the
left) or clockwise (to the right), depending
on the enantiomer
○ The extent of rotation depends on the
concentration of the enantiomer as well as
on its identity
○ The two enantiomers of a pair rotate the
plane-polarized light the same number of
degrees, but in opposite directions
○ Optically Active Compound
● A compound that rotates the plane polarized light
● Achiral compound – are optically inactive
● Chiral molecules – optically active
○ Dextrorotatory compound
● Chiral compound that rotates the plane of polarized
light in a clockwise direction
○ Levorotatory compound
● Chiral compound that rotates the plane of polarized
light in a counterclockwise direction
○ Enantiomers are sometimes called optical isomers
○ Additional Notations
● (+) means rotation to the right (clockwise)
● (-) means roration to the left
(counterclockwise)
○ D-L configuration is not directly related to
+ and – designations
○ D(+)-Mannose – right-handed isomer that
rotates plane-polarized light in a clockwise
direction (to the right)
INTERACTION BETWEEN CHIRAL
COMPOUNDS
○ Enantiomeric pair have the same

interaction with achiral molecules
and different interactions with chiral
molecules
COMPOUNDS
1. Enantiomers have identical:

○ Boiling points
○ Melting points
○ Densities
○ Intermolecular force strength
2. A pair of enantiomers have the same
solubility in an achiral solvent, such as
ethanol, but differing solubilities in a
chiral solvent, such as D-2-Butanol
COMPOUNDS
3. The rate and extent of reaction of

enantiomers with another reactant
are the same if the reactant is
achiral but differ if the reactant is
chiral
4. Receptor sites for molecules within
the body have chirality associated
with them
COMPOUNDS
○ Examples:
● Spearmint (D-Carvone) and Caraway
(L-Carvone)
● D-Epinephrine (perfect fit with the
cellular receptor) and L-Epinephrine
CLASSIFICATION OF MONOSACCHARIDE
○ Only monosaccharide with three to seven

carbon atoms are commonly found in
nature
Number of Carbon Classification

Atoms
3 Triose
4 Tetrose
5 Pentose
6 Hexose
○ Aldose
● A monosaccharide that contains an aldehyde
functional group
● A polyhydroxy aldehyde
○ Ketose
● A monosaccharide that contains a ketone
functional group
● A polyhydroxy ketone
○ The term saccharide comes from the Latin
word for “sugar”, which is saccharum
CHO CH2OH
H C OH C O
H C OH HO C H
H C OH H C OH
CH2OH CH2OH
An aldopentose An ketopentose
BIOCHEMICALLY IMPORTANT
MONOSACCHARIDE
○ D-Glyceraldehyde and Dihydroxyacetone

● The simplest of the monosaccharides
● Are important intermediates in the process of
glycolysis
CHO CH2OH
H OH C O
CH2OH CH2OH
D-Glyceraldehyde Dihydroxyacetone
MONOSACCHARIDE
○ D-Glucose
● Ripe fruits are a good CHO
source of glucose, which
is often referred to as H OH
grape sugar
● Other names are HO H
dextrose and blood
sugar
● The normal glucose in
H OH
human blood is in the
range of 70-100 mg/dL H OH
(1 dL=100 mL)
● Cells use glucose as a CH2OH
primary source of energy
MONOSACCHARIDE
○ D-Galactose
● D-Galactose and D-Glucose are
epimers (C-4) CHO
● Seldom encountered as a free
monosaccharide H OH
● In the human body, it is
synthesized from glucose in the
mammary glands for use in lactose HO H
(milk sugar), a disaccharide
consisting of a glucose unit and
galactose unit HO H
● Also called brain sugar because it is
a component of glycoproteins
(protein-carbohydrate compounds) H OH
found in brain and nerve tissue
● Also present in the chemical CH2OH
markers that distinguish various
tupes of blood – A, B, AB, and O
MONOSACCHARIDE
○ D-Fructose
CH2OH
● Most important ketohexose
● Also known as levulose and C O
fruit sugar
HO H
● The sweetest-tasting of all
sugars H OH
● Found in fruits and honey
● Sometimes used as dietary
H OH
sugar CH2OH
● Different in C-1 and C-2
with D-Glucose
MONOSACCHARIDE
○ D-Ribose
● An aldopentose
CHO CHO
● A component of a
variety of complex H OH H H
molecules such as H OH H OH
RNA and ATP H OH H OH
● The compound 2-
CH2OH CH2OH
Deoxy-D-ribose is
an important D-Ribose 2-Deoxy-D-ribose
component in
nucleic acid
chemistry
ASSIGNMENT
1. Describe the cyclic form of

monosaccharides.
2. How do you write Haworth
Projection formulas?
3. What are the chemical reactions of
monosaccharides?
4. Give some biochemically important
disaccharides and polysaccharides.
CYCLIC FORMS OF
MONOSACCHARIDES
○ Experimental evidence indicates that
for monosaccharides containing five
or more carbon atoms, such open-
chain structures are actually in
equilibrium with two cyclic
structures, and the cyclic structures
are the predominant forms at
equilibrium
CYCLIC FORMS OF
MONOSACCHARIDES
○ Recall:
● Hemiacetals- both –OH and –OR groups
are attached to the same carbon atom
O OH OR'
C + R'OH R C H R C H
R H
OR' OR'
hemiacetal acetal
geminal geminal
ether/alcohol diether
reducing! non-reducing!
CYCLIC FORMS OF
MONOSACCHARIDES
○ Monosaccharides – the –OH and –
OR groups are attached to the
carbonyl carbon
○ The cyclic forms of monosaccharides
result from the ability of their
carbonyl group to react
intramolecularly with a hydroxyl
group
CYCLIC FORMS OF
MONOSACCHARIDES
○ Cyclization of glucose (hemiacetal)
creates a new chiral center at
carbon 1, and the presence of this
new chiral center produce two
stereoisomers, called α and β isomers
CYCLIC FORMS OF
MONOSACCHARIDES
1
CHO
H C OH
2
HO C H D-glucose
3
H C OH (linear form)
4
H C OH
5
CH2OH
6
6 CH2OH 6 CH2OH
5 O 5 O
H H H OH
H H
4 H 1 4 H 1
OH OH
OH OH OH H
3 2 3 2
H OH H OH
α-D-glucose β-D-glucose
CYCLIC FORMS OF
MONOSACCHARIDES
○ In an aqueous solution of D-Glucose,
a dynamic equilibrium exists among
the α, β and open-chain forms, and
there is continual interconversion among
them
CYCLIC FORMS OF
MONOSACCHARIDES
CHO
H OH H OH H OH
HO HO
HO HO H HO
HO H H OH HO OH
H OH H OH
H OH H OH H H
CH2OH
alpha-(+)-glucose beta-(+)-glucose
CH2OH CH2OH
H O H O OH
H
OH H OH H
OH OH OH H
H OH H OH
CYCLIC FORMS OF
MONOSACCHARIDES
1
CH2OH
2C O
HO C H
1 CH2OH
3 HOH2C 6 O
H C OH HO
4 5 H 2
H C OH H 4 3 OH
5
OH H
6
CH2OH
D-fructose (linear) α-D-fructofuranose

CYCLIC FORMS OF
MONOSACCHARIDES
○ Pyranose
● A cyclic monosaccharide that contains a
six-atom ring
○ Furanose
● A cyclic monosaccharide that contains a
five-atom ring
HAWORTH PROJECTION
FORMULA
○ It is a two-dimensional structural
notation that specifies the three-
dimensional structure of a cyclic
form of a monosaccharide
○ It is from Walter Norman Haworth
HAWORTH PROJECTION
FORMULA
○ The D and L of a monosaccharide is
determined by the position of the
terminal CH2OH group on the
highest-numbered ring carbon atom
HAWORTH PROJECTION
FORMULA
○ α and β configuration is determined by the
position of the –OH group on carbon 1
relative to the CH2OH group that
determines the D or L series
○ In a β configuration
● CH2OH and the –OH of carbon 1 point on the
same direction
○ In an α configuration
● The two groups point in opposite directions
HAWORTH PROJECTION
FORMULA
HAWORTH PROJECTION
FORMULA
○ In situations where α and β
configuration does not matter, the –OH
group on carbon 1 is placed in a
horizontal position
HAWORTH PROJECTION
FORMULA
REACTIONS OF
MONOSACCHARIDES
1. Oxidation to acidic sugars

2. Reduction to sugar alcohols
3. Glycoside formation
4. Phosphate ester formation
5. Amino acid sugar formation
1. OXIDATION TO ACIDIC
SUGARS
○ Monosaccharide oxidation can yield
three different types of acidic sugars
depending on the oxidizing agent
used
OXIDATION TO ACIDIC SUGARS
○ Weak oxidizing agent
● Tollen’s and Benedict’s Reagents
● Aldoses are converted into aldonic acid
○ Aldoses are reducing sugars
● Reduces Ag+ to Ag in Tollen’s Reagent
● Reduces Cu2+ to Cu+ in Benedict’s
Reagent
○ A reducing sugar is a carbohydrate
that gives a positive test with Tollen’s
and Benedict’s solutions
○ In basic conditions, ketoses also give
positive results with these reagents
○ These tests are used to test glucose
in the urine
○ The color of the strip is compared
with a chart to determine the
concentration of the glucose in the
urine sample
○ Strong oxidizing agent
● Oxidize both ends of a monosaccharide
at the same time to produce a
dicarboxylic acid, aldaric acid
○ In biochemical systems, enzymes
can oxidize the primary alcohol end
of an aldose to produce alduronic
acid
2. REDUCTION TO PRODUCE
SUGAR ALCOHOLS
○ The carbonyl group can be reduced
to a hydroxyl group using hydrogen
as the reducing agent – sugar
alcohols
REDUCTION TO PRODUCE
SUGAR ALCOHOLS
○ D-Glucitol
● Common name is D-Sorbitol that is
used as moisturizer in foods and
cosmetics
● Used as sweetening agent in chewing
gum because it cannot be used by
bacteria as their food
3. GLYCOSIDE FORMATION
○ Reacting between monosaccharide
and an alcohol
○ Glycoside
● Is an acetal formed from a cyclic
monosaccharide by replacement of the
hemiacetal carbon –OH group with an –
OR group
4. PHOSPHATE ESTER
FORMATION
○ The hydroxyl groups of a monosaccharide
can react with inorganic oxyacids to form
inorganic esters
○ Play important roles in the metabolism of
carbohydrates
5. AMINO SUGAR FORMATION
○ One of the hydroxyl group is
replaced with an amino group
○ The three common natural amino
sugars:
AMINO SUGAR FORMATION
○ Amino sugars and their N-acetyl
derivatives are important building
blocks of polysaccharides found in
chitin and hyaluronic acid
○ N-Acetyl-α-D-glucosamine and N-
Acetyl-α-D-galactosamine
● Are present in the biochemical markers
on red blood cells, which distinguish the
various blood types
AMINO SUGAR FORMATION
DISACCHARIDES
○ A monosaccharide that has cyclic
forms can react with an alcohol to
form a glycoside
○ This is the same process in joining
two or more monosaccharide units
DISACCHARIDES
○ Glycosidic Linkage
● Is the bond in a disaccharide resulting
from the reaction between the
hemiacetal carbon atom –OH group of
one monosaccharide and an –OH group
on the other monosaccharide
● Always carbon-oxygen-carbon bond
DISACCHARIDES
○ Maltose
● Often called malt sugar
● Comes from the breakdown of starch
● Common ingredient in baby foods and
in malted sugar
● Made up of 2 D-Glucose units
● A reducing sugar
DISACCHARIDES
○ Maltose
DISACCHARIDES
○ The most important chemical
reaction of maltose is that of
hydrolysis producing 2 D-Glucose
units
○ Acidic condition is needed or maltase
is needed
DISACCHARIDES
○ Cellobiose
● Is produced as an intermediate in the
hydrolysis of the polysaccharide cellulose
● Like maltose, cellobiose two D-glucose
units but has a β(1→4) glycosidic linkage
CH2OH
O OH
CH2OH β (1-4)
H
O OH
O
OH
OH
OH
OH
Cellobiose
DISACCHARIDES
○ Like maltose, cellobiose is a
reducing sugar, has three isomeric
forms in aqueous solution, and upon
hydrolysis produces two D-glucose
molecules
DISACCHARIDES
○ Lactose
● Is made up of β-D-galactose and a D-
glucose unit joined by β(1→4) glycosidic
linkage
CH2OH
O OH
β (1-4)
CH2OH H
OH
OH O O
OH
OH
OH
Lactose
DISACCHARIDES
○ Lactose - principal carbohydrate in milk.
● Human - 7%–8% lactose
● cow’s milk - 4%–5% lactose
● Lactose intolerance: a condition in which people lack the
enzyme lactase needed to hydrolyze lactose to galactose and
glucose.
● Lactase hydrolyzes β(1-4) glycosidic linkages.
● Deficiency of lactase can be caused by a genetic defect,
physiological decline with age, or by injuries to intestinal
mucosa.
● When lactose is undigested it attracts water causing fullness,
discomfort, cramping, nausea, and diarrhea. Bacterial
fermentation of the lactose further along the intestinal tract
produces acid (lactic acid) and gas, adding to the discomfort.
DISACCHARIDES
○ If not treated, galactosemia can cause
mental retardation in infants and even
death.
○ Treatment involved exclusion of milk and
milk products from diet
○ The α form of lactose is sweeter to the taste
and more soluble in water than the β form
○ The β form can be found in ice cream that has
been stored for a long time; it crystallizers and
gives the ice cream a gritty texture
DISACCHARIDES
○ Sucrose
● Has a head-to-head glycosidic linkage between α-
D-glucose and β-D-fructose with an α, β(1→2)
configuration
CH2 OH
CH2 OH
OH
O
OH OH
OH OH
α-D-Glucose OH
+ OH β (1-2)
O
Linkage
CH2 OH CH2 OH
O OH O
OH OH
CH 2OH CH 2OH
OH OH
β-D-Fructose Sucrose
DISACCHARIDES
○ It is a non-reducing sugar due to the
absence of hemiacetal part in the molecule
○ Sucrase, the enzyme needed to break a
glucose molecule, is present in the human
body
○ It only exists in one form either in solid or in
aqueous solution
EXERCISES
○ Which of the monosaccharides maltose, cellobiose,
lactose, and sucrose has each of the following
structural or reaction characteristics? (There may be
more than one correct answer for a given
characteristic)
a. Two different monosaccharide units are present.
b. Hydrolysis produces only monosaccharides.
c. Its glycosidic linkage is a “head-to-head” linkage.
d. It is not a reducing sugar.
Answers:
a. Lactose, sucrose
b. Maltose, cellobiose, lactose, sucrose
c. Sucrose
d. Sucrose
POLYSACCHARIDES
○ A polysaccharide is a polymer that
contains many monosaccharide units
bonded to each other by glycosidic
linkages
○ Polysaccharides are often also called
glycans
POLYSACCHARIDES
1. The identity of the monosaccharide

repeating unit(s) in the polymer chain.
● Homopolysaccharide
● Heteropolysaccharide
2. The length of the polymer chain.
3. The type of glycosidic linkage between
monomer units
4. The degree of branching of the
polymer chain.
POLYSACCHARIDES
STORAGE POLYSACCHARIDE
○ Is a polysaccharide that is a storage
form for monosaccharides and is used
as an energy source in cells
○ This is done to lower the osmotic
pressure within cells
○ The most important storage
polysaccharides are starch (in plant
cells) and glycogen (in animal and
human cells)
○ Polysaccharides are not sweet and don’t
show positive tests with Tollen’s and
Benedict’s solutions whereas
monosaccharides are sweet and show
positive tests
○ Limited water solubility
○ Examples:
● Cellulose, starch in plants
● Glycogen in animals
● Chitin in arthropods
○ Starch
● A storage polysaccharide is a polysaccharide that
is a storage form for monosaccharides and is used
as an energy source in cells.
● Glucose is the monomeric unit
● Storage polysaccharide in plants
● Two types of polysaccharidse isolated from starch:
● Amylose: Straight chain polymer - 15 - 20% of
the starch and has α(1 ! 4) glycosidic bonds
● Molecular Mass: 50,000 (up to 1000 glucose
units)
○ Amylopectin:
● Branched chain polymer - 80 - 85 % of
the starch α(1!4) glycosidic bond for
straight chain and a (1!6) for branch
● Molecular Mass: 300,000 (up to
100,000 glucose units) - higher than
amylose
● Human can hydrolyze alpha linkage but
not beta linkage
○ Iodine is often used for the presence
of starch in solution
○ Starch-containing solutions turn a
dark blue-black when iodine is added
○ As starch is broken down through
acid or enzymatic hydrolysis to
glucose monomers, the blue-black
color disappears
○ Glycogen
● Contains only glucose units
● Sometimes referred to as animal starch
● Liver cells and muscle cells are the storage
sites for glycogen in humans
● Muscle tissue – approximately 1% glycogen
● Liver tissue – 2-3% glycogen
● This amount is enough to take care the
demands of the body for 15 hours
○ During strenuous activities, glycogen
supplies can be exhausted rapidly
thus the body begins to oxidize fat
as a source of energy
○ Athletes do “carbohydrate loading”
○ When excess glucose is present in the
blood, the liver and the muscle tissue
convert the excess glucose to glycogen for
storage
○ Whenever the glucose blood level drops,
some stored glycogen is hydrolyzed back
to glucose
○ Formation of glycogen reduces osmotic
pressure within the cells and prevents it
from living the cells
STRUCTURAL
POLYSACCHARIDES
○ Cellulose
● Linear homopolysaccharide with β(1→4) glycosidic
bond
● Up to 5000 glucose units with molecular mass of
900,000 amu
● Cotton is approximately 95% cellulose and wood
is approximately 50% cellulose
● Humans do not have cellulase that hydrolizes
β(1→4) linkage so humans cannot digest cellulose
● Some animals have bacteria that produces
cellulase in their guts in order for them to get free
glucose from cellulose
STRUCTURAL
POLYSACCHARIDES
○ In humans, it serves as dietary fiber
in food – readily absorbs water and
results in softer stools and regular
bowel movement
○ 23-35 g of dietary fiber is required
everyday HO
HO O O
OH
HO O O
OH β(1-4) OH
O O
HO
OH β (1-4)
O O OH
OH β(1-4)
O OH
OH
STRUCTURAL
POLYSACCHARIDES
○ Chitin
● Similar to cellulose in both function and structure
● Linear polymer with all b (1!4) glycosidic
linkages - it has a N-acetyl amino derivative of
glucose
● Function is to give rigidity to the exoskeleton s of
crabs, lobsters, shrimp, insects, and other
arthropods HO
HO O O
OH
HO O
O
N-Acetyl
OH HN
O O β-D-Glucoseamine
HO
OH HN O
O O
O OH HN O
HN O
O
ACIDIC POLYSACCHARIDES
○ Acidic polysaccharides - polysaccharides with a repeating
disaccharide unit containing an amino sugar and a sugar
with a negative charge due to a sulfate or a carboxyl group.
○ Structural polysaccharide present in connective tissue
associated with joints, cartilage, synovial fluids in animals
and humans
● Primary function is lubrication necessary for joint
movement
● These are heteropolysaccharides - have more than one
type of monosaccharide monomers is present.
○ Examples:
● Hyaluronic acid
● Heparin
ACIDIC POLYSACCHARIDES
○ Hyaluronic acid:
● Alternating residues of N-
acetyl-b-D-glucosamine and
D-glucuronic acid.
● Highly viscous - serve as
lubricants in the fluid of joints
and part vitreous humor of
the eye.
○ Heparin:
● An anticoagulant-prevents
blood clots.
● Polysaccharide with 15–90
disaccharide residues per
chain.
GLYCOLIPIDS AND GLYCOPROTEINS:
CELL RECOGNITION
○ A glycolipid is a lipid molecule that has

one or more carbohydrate (or
carbohydrate derivative) units
covalently bonded to it.
○ A glycoprotein is a protein molecule

that has one or more carbohydrate (or
carbohydrate derivative) units
covalently bonded to it.
CELL RECOGNITION
○ The lipid or protein part of the

glycolipids is incorporated into the
cell membrane structure and the
carbohydrate (oligosaccharide) part
functions as a marker on the outer
cell membrane surface
CELL RECOGNITION
○ In the human reproductive process,

fertilization involves binding
interaction between oligosaccharide
markers on the outer membrane
surface of an ovulated egg and
protein receptor sites on a sperm
cell membrane
DIETARY CONSIDERATIONS AND
CARBOHYDRATES
○ Foods high in carbs content constitute over 50% of the
diet of most people of the world -- a balanced dietary food
should contain about 60% of carbohydrate:
● Corn in South America
● Rice in Asia
● Starchy root vegetables in parts of Africa
● Potato and wheat in North America
○ Nutritionist divide dietary carbs into two classes:
● Simple carb: dietary monosaccharides or
disaccharides - sweet to taste commonly referred to
as sugars - 20 % of the energy in the US die
● Complex carbs: Dietary polysaccharides -- starch and
cellulose - normally not sweet to taste
GLYCEMIC FOODS
○ A developing concern about intake of
carbohydrates involves how fast the given
dietary carbs are broken down to glucose
within the human body
○ Glycemic effect refers to:
● how quickly carbs are digested
● how high blood glucose rise
● how quickly blood glucose levels return to normal
○ Glycemic index (GI) has been developed for
rating foods

Carbohydrates

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Carbohydrates

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CARBOHYDRATES

Reference: Biochemistry by H.S. Stoker

○ It is the study of the chemical substances

Substances that do Substances that

Water Inorganic salts Protein Lipids Carbohydrates Nucleic Acids

○ Carbohydrates are the most

○ Plants have two main uses for

○ Dietary intake of plant materials is

○ Functions of Carbohydrates in Humans

○ Most simple carbohydrates have

(a polyhydroxy aldehyde) (a polyhydroxy ketone)

○ Upon hydrolysis, oligosaccharides

○ Not all molecules possess handedness

○ Organic molecules, especially

CH2OH H3C CH2OH meansH3C C OH

○ Features that generate

CHO CHO CHO CHO

Are the atoms bonded in the

The molecules are ENANTIOMERS. The molecules are DIASTEREOMERS.

○ It is a two-dimensional structural notation

D- (dextro) means right and L- (levo) means left.

First enantiomeric pair Second enantiomeric pair

CHO CHO CHO CHO

D-isomer (A) L-isomer (B) D-isomer (C) L-isomer (D)

CHO CHO CH2OH CH2OH

○ When plane-polarized light is passed

○ Enantiomeric pair have the same

1. Enantiomers have identical:

3. The rate and extent of reaction of

○ Only monosaccharide with three to seven

Number of Carbon Classification

○ D-Glyceraldehyde and Dihydroxyacetone

1. Describe the cyclic form of

D-fructose (linear) α-D-fructofuranose

1. Oxidation to acidic sugars

b. Hydrolysis produces only monosaccharides.

c. Its glycosidic linkage is a “head-to-head” linkage.

d. It is not a reducing sugar.

1. The identity of the monosaccharide

○ A glycolipid is a lipid molecule that has

○ A glycoprotein is a protein molecule

○ The lipid or protein part of the

○ In the human reproductive process,

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