PROPERTIES

OF
ENANTIOMERS

PRESENTED BY ; JACQUELYN GUINTO

CHARISH GRACILLA
ENANTIOMER

 ENANTIOMER exhibit different properties in

only two areas;

 Their interaction with plane polarized light end

 Their interaction with chiral substances
INTERACTIION OF ENANTIOMERS
WITH PLANE-POLARIZED LIGHT

 The plane of POLARIZED LIGHT can be

rotated , the two enantiomers of a pair rotate
the plane POLARIZED LIGHT the same
number of degrees ,but in opposite directions.
 All lights move through space with a wave
motion .
 Ordinary light waves or UNPOLARIZED
LIGHT wave vibrate in all ordinary planes at
right angles to their direction of travel
INTSTRUMENTS USED

 INTRUMENTS USED TO MEASURE THE

DEGREE OF ROTATION OF PLANE
POLARIZED LIGHT BY ENETIOMERIC
COMPOUNDS OR POLARIMETERS
DEXTRORATATORY COMPOUNDS AND
LEVOROTATORY COMPOUNDS

 DEXTRORATATORY COMPOUND is chiral

compound that rotates the plane of polarized
light inCLOCKWISE DIRECTION .

 LEVOROTATORY COMPOUND is a chiral

compound that rotates the plane of polarized
light in a COUNTER CLOCKWISE
DIRECTION
 NOTE
 In any pair of enantiomers , one ,the +
enantiiomer always rotates the plane of polarized
light to the right and – enantiomer to the left .

 The + or – are not connected entities .

 Not all D enantiomers will rotate plane polarized
light in the same direction.
INTERACTION BETWEEN CHIRAL COMPOUND

 a CHIRAL compound has a mirror image that

cannot line up with it perfectly . The mirror
images are non-superimposable the opposite
of chiral compound is ACHIRAL objects are
supeerimposable with their mirror images.
EXAMPLE

 A left handed baseball player and a right

handed baseball player can use the same can
use the same baseball bat of baseball hat
however they cannot use thev same baseball
gloves.
 It is found out that the two member of an
enantiomer pair have the same interaction with
ACHIRAL molecules and different
inteeractoions with CHIRAL MOLECULES.
NOTE

 Intermolecular force strenght is the reason why the

enantiomers have identical boiling points , melting
ppoints an densities .
 A pair of enantiomer have the same solubility in
an ACHIRAL SOLVENT while in CHIRAL
SOLVENT the solubilities are diffeerent.
 Receptor sites the molecules within the body have
CHIRALITY associated . Sometimes the
responses are only slightly different and at other
times very different.
 CLASSIFICATION
OF
MONOSSACHARIDE
S
NOTE

 MONOSACCHARIDES from greek monos;

single, sacchar sugar also called SIMPLE
SUGAR .
 They cannot be further hydrolyzed to simpler
chemical compound .
 The carbon atoms that can be presented in
monosaccharides is no limit . Only
monosaccharide with three to seven carbon
atoms are commonly found in nature.
 MONOSACCHARIDES are classified as
ALDOSES or KETOSES on the basis of what
type og carbonyl group is present .
 It is often classified by their number of carbon
and their functional group
 BIOCHEMICALLY
IMPORTANT
MONOSACCHARIED

PRESENTED BY; LIANNA ALAO

D-GLYCERALDEHYDE AND DIHYDROXYACETONE

Simplest of the monosaccharide

Important intermediates in the process of
glycolysis
Converted into two molecules of pyruvate. D-
Glyceraldehyde is a chiral molecule, but
dihydroxyacetone is not.
 Two other names for D-Glucose are dextrose and blood sugar.
It is the most abundant in nature and the most important from a human
nutritional standpoint.
Its Fischer projection formula is :

Ripes fruits, particularly grapes ( 20%- 30% glucose by mass), are good
source of glucose. Which is often referred to us as grape sugar.
D- Glucose

70-100 ml/dL ( 1 dL = 100 ml) normal

concentraticon.
The actual concentration is dependent on the
time that has elapsed since the last meal was
eaten.
130 ml/dL concentration in the first hour after
eating. Then returns back to normal after 2-3
hours.
 Two hormones, insulin and glucagon
Have important role in keeping glucose blood
concentration within the normal range, which
is required for normal bodyb function. An
abnormal functioning leads to the condition
called diabetes.
D- Galactose

 A comparison of the Fischer projection formula

for D- galactose and D- glucose shows that this
two compounds differ only in the configuration of
the OH group and H group on carbon
D- Galactose

 D- Galactose
It is a free monosaccharide.
It is a component of numerous important biochemical
substances.
 Synthesized from glucose in the mammary glands for
use in lactose (milk sugar).
Also called as “ brain sugar “ because it is a component
of glycoproteins found in brain and nerve tissue.
It is also present in the chemical markers that distinguish
various types of flood ( A, B, AB, and O ).
D- Fructose

 D- Fructose
Is the most biochemically the most important
ketohexose.
It is also called levulose and fruit sugar.
The sweetest tasting of all sugars, it is found in many
fruits and is present in honey in equal amounts with
glucose.
It is sometimes used as a dietary sugar, not because it
has fewer calories per gram than other sugars but
because it is less needed for the same amount of
sweetness
D- Ribose

 D- Ribose
 D-Glucose, D-Galactose, and D-Fructose are all hexoses. D- Ribose is
apentose. If carbon 3 and its accompanying – H and OH groups were
eliminated from the structure of D-glucose , the remaining structure
would be that of D- Ribose
It is a component of a variety of complex molecules,
including ribonucleic acids (RNAs) and energy-rich
compounds such as adenosine triphosphate ( ATP) .
The compound 2-deoxy-D-ribose is also important
nucleic acid in chemistry. This monosaccharide is a
component of DNA molecules.
The prefix deoxy means “ minus an oxygen” ; the
structures of ribose and 2-deoxyribose differ in that
the latter compound lacks an oxygen atom at carbon
2
 THANK YOU
PRESENTED BY; LIANNA P. ALAO
CYCLIC FORMS OF
MONOSACCHARIDE

PRESENTED BY ; PRINCE RYAN P. CUELLO

CYCLIC FORMS OF
MONOSACCHARIDE

 MONOSACCHARIDES THAT FORM

STRUCTURES.
 ring consisting of fivr or six carbon atoms are
more stable.
PYRANOSE

 COLLECTIVE TERM FOR SACCHARIDES

THAT HAVE CHEMICAL STRUCTURES
THAT INCLUDES SIX MEMBERED RING
CONSISTING OF FIVE CARBON ATOM
AND ONE OXYGEN ATOM
FURANOSE

 COLLECTIVE TERM FOR

CARBOHYDRATES THAT HAVE
CHEMICAL STRUCTURE THAT
INCLUDES A FIVE MEMBERED RING
SYSTEM CONSISTING OF FOUR
CARBON ATOM AND ONE OXYGEN
ATOM
 HAWORTH
PROJECTION
FORMULAS

PRESENTED BY; NICOLE IGNO

 A Haworth projection formula is a two- dimensional structure
notation that specifies the three-dimensional structure of a cyclic
form of a monosaccharide. Such projections carry the name of
their originator, the British chemist Walter Norman Haworth.
 Walter Norman Haworth (1883-1950),developer of Haworth
Projection Formulas Was a British Carbohydrate chemist. He
helped determine the structure of the cyclic forms of glucose was
the first to synthesize vitamin C, and was a corecipient of the
1937 Nobel prize in chemistry.
 In a Haworth Projection, the hemiacetal ring system is viewed
“edge on” with the oxygen ring at the upper right (six-membered
ring) or at the top (five membered ring).
 The D or L form of a monosaccharide is
determined by the position of the terminal
-CH2OH group on thee highest-numbered ring
carbon atom.In the D form, this group is
positioned abouve the ring. In the L form,
which is not usually encountered in
biochemical systems the terminal –CH2OH
group is positioned below the ring.
 a or β configuration is determined by the
position of the –OH group on carbon 1 relative
to the –CH2OH group that determined D or L
series. In a β configuration, both of these
groups point in the same direction ;in an a
configuration, the two groups point in opposite
directions.
 In situation where a or β configuration does not
matter, the –OH group on carbon 1 placed in a
horizontal position, and a wavy line is used as the
bond that connects it to the ring.
 The specific identity of a monosaccharide is
determined by the positioning of the other –H
groups in the Haworth projection formula. Any
–H group at a chiral center that is to the right in
a Fischer projection formula points down in the
Haworth projection formula. Any group to the
left in a Fischer projection formula points up in
the Haworth Projection formula. The following
is a matchup between Haworth projection
formulas and a fischer projection formula.
 A similar matchup diagram for L-mannose shows that
all up and down positions are inverted to the D-
mannose diagram.
Changing a Fischer Formula to a Haworth
Projection Formula
 Draw the Haworth projection formula for both
anomers of D-talose, a monosaccharide whose
Fischer projection formula is
Solution:

D-Talose is an aldohexose. An aldohexose cyclization

produces a six-membered ring with one carbon atom (c6)
outside the ring .
Step 1: Draw a planar hexagon ring with the oxygen atom in
the upper right corner of the ring.
Step 2:

 add a- CH2OH group to the first carbon to the left of the

ring oxygen atom. This attachment up since the
monosaccharide is D-talose rather then L-talose. For L-
talose, the -Ch2Oh group would have bee drawn down.
Step 3:

 add to the anomeric carbon, first carbon to the

right of the ring oxygen, a-OH group that id
drawn down for the a-anomer drawn up the
Step 4:

 Add an –OH group to ech of the remaning

three carbons atoms .the –--OH group is drawn
down if I was to the right in the fisher
projection and drawn down if it was to the
right in the fisher projection formula and
drawn up if it was to the left in the left in the
fisher projection formula
 REACTIONS OF
MONOSACCHARIDES
BIOCHEMISTRY CHAPTER 1: CARBOHYDRATES

PRESENTED BY ;LEA ALTERADO

Why do we need to study this?

 Monosaccharides are the basic unit of

carbohydrates that make up more complex
structures of carbohydrates like di-, oligo-, and
polysaccharides. Studying this can help us
understand how different compounds can be
recycled in the body to produce others .
Five Important Reactions of Monosaccharides

 1. Oxidation
 2. Reduction
 3. Glycoside Formation
 4. Phosphate Ester Formation
 5. Amino Sugar Formation

 The monosaccharide reactant will be:

Glucose
The chemical reactions that the monosaccharides
will undergo will depend on these functional
groups:

 Aldehyde Group
 Ketone Group
Oxidation

Monosaccharide oxidation can yield 3 types of

acidic sugars using weak oxidizing agents (such
as Tollens and Benedict’s solutions)
oxidation of the aldehyde end of:
 Aldose give aldonic acid
 Glucose give gluconic acid
 Galactose give galactonic acid
A reducing sugar is a carbohydrate that gives a
positive test with Tollens and Benedict’s
solutions. Thus all monosaccharides, both aldose
and ketose are reducing sugars.

2. Strong oxidizing agents (such as carbonyl

group and the terminal primary alcohol group)
can oxidize both the ends of a monosaccharide
at the same time to produce dicarboxylic acid.
The structures involved in glucose reaction are:
Reduction
leads to the formation of sugar alcohols/alditols

 The carbonyl group present in a monosaccharide

(either an aldose or ketose) can be reduced to a
hydroxyl group using, hydrogen as the reducing
agent.

Reduction of:
Glucose = Glucitol or also known as Sorbitol
Galactose= Dulcitol
Mannose= Manittol
Fructose = Manitol + Sorbitol
  Glucitol or also known as Sorbitol have
similar properties to those of the
trihydroxy alcohol glycerol.

 These alcohols are also used as

moisturizing agents in food and in
cosmetics.

 Sorbitol is also used as a sweetening agent in

chewing gum.
Glycoside Formation
production of acetals

 The cyclic forms of monosaccharides are hemiacetals which are

shown to react with alcohols in acid solution to produce acetals or
generally called as glycoside.

 A glycoside is an acetal formed from a cyclic monosaccharides by

replacement of hemiacetal carbon –OH or –OR group.
 Glycoside formed
from:
 Glucose produce Glucoside
 Galactose produce Galactoside
and so on
Phosphate Ester Formation
 The hydroxyl groups of a monosaccharide can react with the
inorganic oxyacids to form inorganic esters
 Phosphate esters formed from phosphoric acid and various
monosaccharides are commonly encountered in biochemical systems
 Phosphate esters of glucose are stable and play important role in
metabolism of carbohydrates
Amino Sugar Formation

 Amino sugars such as D-glucosamine and D-galactosamine

contain an amino group (instead of hydroxyl group) at carbon
2 position.
 Amino sugars and their N- acetyl derivatives are important
building blocks of polysaccharides found in chitin and
hyaluronic acid
 There are 3 common amino sugars namely: glucosamide,
galactosamide, and mannosamide
THANK YOU
GROUP 1

MADE BY : RECENTES, RENEL

YAQUIT, JHERBELENE ANN
 DISACCHARIDES
 A disaccharide
 ( also called a double sugar or bivose )
 Is a sugar formed when monosaccharides ,
 ( simple sugar ) are joinedby GLYCOSIDIC LINKAGE.
 GLYCOSIDIC LINKAGE IS THE BOND THAT LINK TWO
MONOSACCHARIDES OF A DISACCHARIDE
( GLUCOSIDE ) TOGETHER.
 DISACCHARIDE are foremed through DEHYDRATION
reactions in which a total of one water molecule is removed
from the two monosaccharides.
 DISACCHARIDES are carbohydrates found in many
foods and often added as sweeteners , SUCROSE for
example, is a table sugar ,and it’s the MOST
COMMON DISACCHARIDE that humans eat .also
found in BEETROOT.
 When DISACCHARIDE like SUCROSE are
digested ,they are broken down to their simple sugars
and used for energy .
 MALTOSE
SUCROSE
Often called “malt
Sucrose is
Sucrose is common
common sugar.
sugar. sugar or
It is
It is aa disaccharide,
disaccharide, aa
maltobiose”, is a
molecule composed
molecule composed of of two
two
monosaccharide: glucose
monosaccharide: glucose sugar produced by
and fructose.
and fructose. Sucrose
Sucrose is is the breakdown of
produced naturally
produced naturally inin starch, e.g. by
plants, from
plants, from which
which table
table enzymes found in
sugar is
sugar is refined.
refined. It
It has
has the
the
malt and saliva.
molecular formula
molecular formula
C₁₂H₂₂O₁₁
C₁₂H₂₂O₁₁ Formula: 
C₁₂H₂₂O₁₁
 Lactose
It is a sugar composed of
galactose and glucose
subunits. Lactose makes up
around 2–8% of milk. The
name comes from lac, the
Latin word for milk, plus
the suffix -ose used to name
sugars. It has the molecular
formula C₁₂H₂₂O₁₁
Cellobiose
Cellobiose is a disaccharide
and a reducing sugar
consisting of 2 beta-glucose
molecules which are linked to
each other by a beta
(1-->4) bond. It can be
hydrolyzed to glucose
enzymatically or with an acid
 LACTOSE INTOLERANCE or LACTASE
PERSISTENCE

 Lactose Intolerance is the inability to

digest lactose, which is a type of sugar
found in milk and dairy products. Lactase
is the enzyme that digests lactose. Some
people lack the ability to produce lactase
and some people produce very little of it.
The symptoms are bloating, cramping,
nausea and diarrhea.
OLIGOSACCHARIDE
S

PRESENTED BY;
PRINCE RYAN P. CUELLOAnd
MA SHAINA KITCHON
OLIGOSACCHARIDES

Any Carbohydrate whose molecules are composed

of a relatively small number of monosaccharide
units via Glycosidic linkages

*COMPOSED OF 3 TO 10
MONOSACCHARIDES.
WHAT ARE GLYCOSIDIC LINKAGES?

A type of covalent bond that joins

carbohydrate molecule to another group which
may or may not be another Carbohydrate

FORMED BETWEEN HEMIACETAL OR

HEMIKETAL GROUP OF SACCHARIDE
AND HYDROXYL GROUP OF SOME
COMPOUND AS AN ALCOHOL.
 An important aspect of the human body
chemistry that involves oligosaccharides as
components of more complex molecules is
Blood Chemistry associated with blood type.

 The type of blood that a person has (O,A,B

and AB) is determined by the type of
oligosaccharide that is attached to a person’s
Red Blood Cells.
BIOCHEMICAL MARKERS

Galactose
Fucose
N-acetyl Glucosamine
N-acetyle Galactosamine
•Arrangements of these monosaccharides in the
biochemical marker determines the blood type
SOLANINE

 Solanine, is a compound found in the potato

plant, is another example of an
oligosaccharide-containing “complex
molecule”
POLYSACCHARIDE
 Polysaccharide is a polymer that contains
many monosaccharide untis bonded to each
other by glycosidic linkage.
 A glycosidic bond is formed between
hemiacetal or hemiketal group of saccharide
and the hydroxyl group of some compound
such as an alcohol.
HOMOPOLYSACCHARIDE

 Is a saccharide in which only one type of

monosaccharide monomer is present.
HETEROPOLYSACCHARIDE

 Is a polysaccharide in which more

than one (usually 2) type of
monosaccharide monomer is present.
POLYMER CHAIN

 A carbon atom bonded to 2 hydrogen atoms

can be considered a building block unit of the
polymeric chain.

*100-50,000 monomer units

STARCH

 Is a homopolysaccharide containing only

glucose monosaccharide units. It is the energy
storage polysaccharide in plants.
GLYCOGEN

 Is a polysaccharide containing only glucose unit. It is the

glucose storage polysaccharide in Humans and Animals.
 Its functions is similar to starch in plants and is sometimes
referred as an animal starch.
 STORAGE
POLYSACCHARIDE
S

PRESENTED BY;
KRINGBEL DIANNE MARQUEZ
And
KIMBERLY SOLIS CASTOR
WHAT IS STORAGE POLYSACCHARIDES?

A storage polysaccharides is a
polysaccharide that is a storage form for
monosaccharides and is used as an energy
source in cells.
 The most important
storage polysaccharides are starch (in plant
cells) and glycogen (in animal and
human cells).
 STARCH
 Starch is a homopolysaccharide containing
only glucose monosaccharide units.
 It is the energy-storage polysaccharide in
plants.
 Two different polyglucose polysaccharides
can be isolated from most starches: amylose
and amylopectin
 Amylose, an unbranched-chain glucose
polymer, usually accounts for 15% - 20% of
the starch.
 Amylopectin, has a high degree of branching
in its polyglucose structure. Accounts for the
remaining 80% - 85% of the starch.
 Iodine is often used to test for the presence of
starch in solution.
 GLYCOGEN
 is a polysaccharide containing only glucose
units.
 is the glucose storage polysaccharide in
humans and animals.
 It has a structure similar to that of
amylopectin.
 is an ideal storage for glucose.
STRUCTURAL
POLYSACCHARID
ES
 What is structural polysaccharides?

 A structural polysaccharide is a
polysaccharide that serves as a structural
element in plant cell walls and animal
exoskeletons.
 Two of the most important structural
polysaccharides are cellulose and chitin.
 Both are homopolysaccharides.
CELLULOSE

 Cellulose, the structural component of plant cell

walls, is the most abundant naturally occurring
polysaccharide.
 Cellulose is an unbranched glucose polymer.
 Typically, cellulose chains contain about 5000
glucose units.
 Cellulose is not a source of nutrition for human
beings
 Cellulose is still an important component of
balanced diet.
Structure of • Structure for chitin
cellulose
CHITIN
 Chitin is the second most abundant naturally
occurring polysaccharide.
 It also been found in the cell walls of fungi.
 It’s function is to give rigidity to the
exoskeletons of crabs, lobsters, shrimp,
insects, and other arthropods
EDIBLE FIBERS AND HEALTH
Edible fibers, that is, nondigestible
carbohydrates, can be classified in two
different ways. In the first classification
system there are two types of edible
fibers: functional fiber and dietary fiber.
Functional fiber is nondigestible
carbohydrate material that have been
produced commercially for use in
fortifying foods or in fiber supplements.
Dietary fiber is nondigestible
carbohydrate materials that are used
intact as they occur naturally in foods.
In the second classification system for edible
fibers classification: insoluble or soluble
 Insoluble fiber is nondigestible carbohydrate
materials, that do not form viscous materials
that is, materials that have a gel-like
consistency in water.
 Soluble fiberis nondigestible fiber materials
that dissolve in water to produce thick liquids
with a gel-like consistency.
Included in the high-fiber diet are the following

 Digestive Tract Health – Dietary fiber

provides the digestive tract with ‘bulk’.
 Reduction in Heart Disease Risk –
Consuming 5-10 g of soluble fiber per day
reduces blood cholesterol levels by 3% -
5%
Blood Glucose Control – Delays the
transmit of other materials through the
digestive system.
Weight Management – It is known that
foods high in fiber tend to low in fat and
added sugar.

One common misconception about

fiber is that fresh fruit and vegetables
contain more fiber than their canned
counterparts.