Unit 3. Lesson 1. Carbohydrates

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FOOD

Carbohydrates
v BASIC CONSTITUENTS OF FOOD

¢ FOOD is any substance usually composed of


carbohydrates, fats, proteins, water etc that can be
eaten or drunk by human for nutrition
¢ The constituents of foods are divided into two

MAJOR MINOR
Carbohydrates Vitamins
Fats Minerals
Proteins Enzymes
Pigments
Flavors
& Acids
¢ There is also the ever present and important
constituent is Water

¢ All these constituents are arranged in foods to give


the foods their:-

ü Structure
ü Texture

ü Flavor

ü Colour

ü & Nutritive value


v CLASSIFICATION OF FOODS

v Foods are classified, according to their functions in


the body
v Energy Yielding Foods

ü This group includes foods rich in carbohydrates &


fats
ü 1 gm of CHO yields 4 calories

ü 1gm of fat yields 9 calories

v It is divided into two:-

ü Pure Carbohydrates like sugar, fats & oils

ü Cereals, pulses, roots & tubers


¢ Sugarsprovide energy & Fats and oils also provide
concentrated source of energy

¢ Cerealsprovide in addition to energy large amounts


of proteins, minerals and vitamins in the diet

¢ Pulsesalso give proteins and vitamins besides


giving energy to the body

¢ Roots & tubers mainly provide energy but they also


contribute to some extent vitamins & minerals
v BodyBuilding Foods
¢ Foods rich in proteins are called Body Building
Foods
¢ 1 gm of CHON yields 4 calories

v They are classified into two groups

ü Milk, Meat, Egg & Fish: – They are rich in proteins


of high biological value. These proteins have all the
essential amino acids in correct proportions for the
synthesis of body tissues

ü Pulses, Oil-seeds & Nuts: - They are rich in protein


but may not contain all the essential amino acids
required by the human body
v Protection & Regulation
v Foods rich in proteins, vitamins & minerals have
regulatory functions in the body
ü E.g. maintaining heart beat, body temperature,
clotting of blood & excretion of wastes

v Protective foods are classified into two groups:-


Ø Foods rich in vitamins, minerals & proteins of

High biological value


ü E.g. Milk, egg, fish & liver

Ø Foods rich in certain vitamins & minerals only

ü E.g. Green leafy vegetables & some fruits


CARBOHYDRATES
v CARBOHYDRATES

¢ Carbohydrates
are organic compounds made up of
carbon, hydrogen, & oxygen

¢ Carbohydrates
are polyhydroxy aldehydes or
polyhydroxy ketones and their derivatives

¢ Commonly, the hydrogen & oxygen in the


carbohydrates are present in 2:1 ratio as in water, from
which the name carbohydrate (carbon Hydrate) was
derived
¢ CHO are sometimes referred as saccharides meaning
sugar

¢ Simple CHO are called sugars

¢ One of the simplest carbohydrates is glucose (C6H12O6) or


monosaccharide & they link together to form more
complex carbohydrates (oligo or polysaccharides )

¢ The names of most CHO are characterized by ending


“OSE”

ü E.g., Glucose
ü Lactose - Milk Sugar
ü Maltose- Malt sugar
ü Fructose- Fruit Sugar
¢ CHO occur in many plant & animal tissues, as well
as microorganisms

¢ Inanimal organism the main sugar is glucose &


storage CHO is glycogen, in milk the main sugar is
the disaccharide lactose

¢ Inplant organism a wide variety of monosaccharides


and oligosaccharides [composed of 3-6 mono (disacc,
polysacc)] occur & the storage carbohydrate is
starch. The structural polysaccharide of plant is
cellulose.
CLASSIFICATION OF CARBOHYDRATES
CLASSIFICATION OF CARBOHYDRATES
v
v DIGESTABLE & INDIGESTIBLE CHO

¢ Dietary carbohydrates may be categorized as


digestible & Indigestible based on their ability to
digest by enzymes present in saliva, stomach or
intestine

ü DIGESTIBLE:- Dietary CHO may be categorized as


digestible by enzymes present in the saliva, stomach
or intestine or absorbable without digestion
Ø E.g., Lactose, Sucrose, Human milk, Vegetable starch

ü INDIGESTIBLE:- E.g., Dietary fibers found in


cereals, Vegetables & fruits & fructo oligosaccharides
such as inulin, present in certain vegetables &
processed foods
v Depending upon whether or not they undergo HYDROLYSIS
Monosaccharides Disaccharides Trisaccharides Polysaccharides
v Made up of 2- 6 v Made up of 2 v Made up of 3 vContain 10 or more
carbon units monosaccharides monosaccharides monosaccharide units

ü Glucose üSucrose ü Dextrin


(Glucose+Fructose) ü Raffinose
ü Fructose ü Starch
üMaltose
ü Galactose (Glucose+Glucose) ü Cellulose

ü Lactose ü Hemicellulose
(Glucose+Galactos)
ü Pectin

ü Gums
v MONOSACCHARIDES
¢ It consists of a single polyhydroxy aldehyde or ketone
group and is commonly known as simple sugars

¢ These can’t be hydrolyzed into simpler forms

¢ Serve as the building blocks of complex sugars and


polysaccharides

ü E.g. Glucose, Fructose, Galactose

¢ The general formula is (CH2O)n where n is 3 to 7

¢ Monosaccharides with 5 & 6 carbon atoms are more


common
¢ All
the carbon atoms contain one hydroxyl (–OH )
group and sometimes one carbonyl oxygen (as in –
CHO, or C=O)

v Based on functional group monosaccharides are


classified in 2 types-

v ALDOSES

v KETOSES
v ALDOSES

¢ Ifthe carbonyl oxygen group is present at the terminal


position, the monosaccharide is an aldehyde
derivative and the sugar is called aldose sugar
ü Eg. Glucose

¢ The aldoses contain an aldehyde ( ) group

GLUCOSE
v KETOSES

¢ Ifit is present in any other position, the


monosaccharide is a ketone derivative that is known as
ketoses
ü E.g., Fructose

¢ Ketoses which contain a ketone ( )group

FRUCTOSE
v Numbering of carbon atoms in Monosaccharides
¢ The carbon atoms are numbered as ………………
C - 1 is an aldehyde functional group & C- 2 is a
ketone functional group

GLUCOSE FRUCTOSE
v Monosaccharides can further be divided on the basis of
the number of carbon atoms they possess

¢ The number of carbon atoms in an aldose or ketose


may be specified by
ü Triose

ü Tetrose

ü Pentose

ü Hexoses

Ø For ex. Glucose with six carbon atom is an aldohexose


Fructose with six carbon atom is a ketohexose
v DIFFERENT TYPES OF MONOSACCHARIDES
Monosaccharide Specific Example

No. Called as Aldoses Ketoses


Carbon
atoms

3 Triose

4 Tetrose
5 Pentoses

6 Hexoses
ISOMERISM OF MONOSACCHARIDES
v ISOMERISM OF MONOSACCHARIDES

¢ Existence of different compounds having same


molecular formula but different structural forms are
isomers

¢ Monosaccharides exhibit a variety of isomerism such as

ü Aldose- Ketose isomerism

ü Sterio isomerism

ü Optical isomerism
v ALDOSE- KETOSE ISOMERISM
¢ In a monosaccharide either an aldehyde or a ketone
group is present. The former is called aldose while the
latter is known as Ketose
¢ Glucose & fructose both have a formula C6H12O6 but
glucose is an aldohexose (aldehyde bearing hexose) &
fructose is a Ketohexose (Ketone bearing hexose), so
they are isomers to one another
v OPTICAL ISOMERISM

¢ When an optically active substance rotates the plane of


polarized light in a clockwise direction, it is called as
dextrorotatory or ‘d- isomer’ & when it rotates the
plane polarized light in the anticlockwise direction, it is
laevorotatory or ‘l- isomer’ of the substance
¢ Thed & l isomers are also expressed as (+) & (-)
respectively
¢ The two forms of glyceraldehydes (d & l forms) rotate
the plane of polarized light in the opposite direction by
the same amount
¢ As it turns out D- Glyceraldehyde rotates the plane of
polarized light to the right & is therefore dextrorotatory
labelled as (+) & rotates the plane of polarized light to
the left & is therefore laevorotatory labelled as (-)
¢ The D- form will have the –OH group next to the
bottom carbon atom (primary Alcohol group) on the
right side, while the L- form will have it on the left
side

¢ i.e.,the D- form will have the –OH group on the


right side of the penultimate C- atom (C- atom
away from functional group & near to terminal C-
atom) , while the L- form will have it on the left side
of the penultimate C- atom
v Enantiomers:

v Themirror images of stereo isomers are known as


enantiomers
STRUCTURE OF CARBOHYDRATES
v STRUCTURE OF CARBOHYDRATES

v Carbohydrates are represented by three types

ü Fischer Projection

ü Haworth Cyclic Structure

ü Conformational formula
v FISCHER PROJECTION
v CYCLIC HEMIACETAL FORMS OF D-GLUCOSE

¢ Aldohexose, Ketohexose & aldo


pentose in solution undergo
cyclisation when treated with
equivalent amounts of alcohol & form
a Hemiacetal in the aldose or
hemiketal in the ketose
¢ The glucose structure contains an
aldehyde group & five hydroxyl
group in the same molecule
¢ Consequently there can be
intramolecular interaction between
the carbonyl group & one of the
hydroxyl group

¢ The hydroxyl group on C5 is able to


react with the carbonyl group on C1
to produce a closed pyranose ring

¢ The reaction results in a ring i.e., the


product is cyclic hemiacetal
¢ Thesix membered ring shown for α & β- D glucose is
known as pyran ring because pyran is the name of a
heterocyclic compound whose ring consists of five
carbon atoms & one oxygen atom

¢ AnyCHO containing a six membered ring is called


pyranose & its glycosides are called pyranosides
¢ TheHaworth formula for α– D glucose shows the C1 -
OH group below the plane of the pyranose ring, for
β- D glucose C1 alcohol pointing above the plane of
pyranose ring
¢ i.e.,
the α- form has the – OH group on the opposite
side from the – CH2OH & β- form has the –OH group
on the same side as the CH2OH group
¢ A carbohydrate containing a five membered ring is
called furanose because furan is the name of a
heterocyclic compound whose ring consists of four
carbon & one oxygen atom
¢ The glycosides of furanose are called furanosides

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v PROPERTIES OF MONOSACCHARIDES:

¢ The taste is sweet

¢ They are solid at room temperature

¢ They are soluble in water because of the hydroxyl


group; the very concentrated solutions are thick
ü E.g.: Honey
¢ There are reducing sugars containing potential
reducing group such as free aldehydes or ketone have
the ability to reduce Fehling’s solution & Tollen’s
reagent are referred to as reducing sugars
ü E.g.; glucose & fructose

¢ Aldoses have an aldehyde (CHO) group can be easily


oxidized to COOH (Carboxylic group). For this reason
they are called reducing sugars

CHO COOH

¢ Ketose have a hydroxyl (–OH) group on the carbon


next to the carbonyl group which can be oxidized &
they are called reducing sugars
v CARAMELIZATION

¢ Itis non- enzymatic browning


¢ Caramelization occurs during dry heating and roasting
of foods with a high concentration of carbohydrates
(sugars)
¢ When sugars are subjected to heat in the absence of
water or are heated in concentrated solutions a series of
reactions occur that finally leads to caramel formation
¢ Typical caramel flavor is the result of a number of
sugar fragmentation reactions (flavour production) &
dehydration products, including diacetyl, acetic acid
& formic acid
¢ Caramelization results from the action of the heat on
sugars at about 175° C
¢ At high temperature sugars dehydrate, break down
& polymerize (polymerization reactions, colour
production) into viscous caramels, the chemical
changes associated with melting sugars result in a
deep brown amber color & new flavors

ü E.g., is the Browning of bread- when toasted in


which, caramelization takes place under the oven heat
& the sugar adds golden brown, flavorful & slightly
crisp surface that tastes great & helps retain moisture
in the product

¢ Once the melting point has been obtained the sugars


will caramelize
¢ Each sugar has its own caramelization temperature

ü Galactose
ü Sucrose Caramelize at about 160° C
ü & glucose

ü But fructose caramelizes at 110° C

ü & maltose caramelizes at about 180° C

¢ Caramel has a pungent taste, is often bitter, is much


less sweet than the original sugar from which it is
produced & soluble in water
DERIVED MONOSACCHARIDES
v DERIVED MONOSACCHARIDES

¢ This group includes compound which are structurally


similar to the monosaccharides but deviating from
them in some regard

¢ There are two important derivatives

ü DEOXY SUGARS

ü AMINO SUGARS
v DEOXY SUGARS

¢ Sugarsin which one of the hydroxyl group


is replaced by a hydrogen atom, are
known as deoxy sugars

¢ Thecommon example is deoxy ribose


found in nucleosides, nucleotides & nucleic
acids (DNA)
v AMINO SUGARS

¢ Sugars in which hydroxyl group has been replaced


by an amino group are known as amino sugars

ü For example D- Glucosamine, D- galactosamine, D-


mannosamine, all of these are found in a wide variety
of biological materials

¢ Glucosamine is the product of hydrolysis of chitin,


the major polysaccharide of shells of insects &
crustaceans
v OLIGOSACCHARIDES

¢ Theoligosaccharides are carbohydrates contain 3 to


<10 monosaccharide units joined by a linkage known
as glycosidic linkage

¢ Theyare classified as di, tri, tetrasaccharides etc


depending on the number of subunits

¢ They can be hydrolyzed by acids or enzymes into


their subunits
v DISACCHARIDES
¢ These are formed when 2 monosaccharide molecules
joined together with the elimination of one molecule
of water
¢ i.e., these consists of two monosaccharide units/
molecules joined by glycosidic linkage

¢ They have the general formula C12H22O11, upon


hydrolysis which yield two monosaccharide
molecules

¢ Ex. of disaccharides are :-

ü Sucrose, Lactose, Maltose


v SUCROSE

¢ It is the ordinary household sugar

¢ The most common sources are sugar cane & sugar


beets

¢ In sucrose both the carbonyl groups are involved in


the formation of glycosidic bond

¢ So sucrose contains no active group i.e., both the


reducing groups are involved in linkage, so it is a
non- reducing sugar
¢ Itis formed by the elimination of a molecule of water
from Glucose & fructose

¢ The figures in brackets indicate the position of the


glycosidic linkage between the two monosaccharide
units
v MALTOSE

¢ It is α–D glucosyl- 1, 4 – D glucose

¢ Maltoseis a malt sugar, found in germinating cereals,


produced during digestion of starch into glucose

¢ It’s
a reducing sugar because only one reducing
group forms the linkage

¢ On hydrolysis yields two molecules of glucose


¢ Maltoseconsists of 2 molecules of glucose with a
glycosidic linkage formed between the anomeric
hydroxyl of one glucose unit & the hydroxyl on the
fourth carbon atom
v ISOMATOSE

¢ Itsstructure is similar to maltose, except it has an α-


1,6 glycosidic linkage

α D glucopyranosyl (1,6)- α D glucopyranose


v LACTOSE
¢ Itis milk sugar
found in milk of
mammals

¢ Less sweet than sucrose

¢ It’sa reducing sugar


because the reducing
groups of glucose
doesn't take part in
linkage

¢ On hydrolysis yields
one molecule each of
glucose & galactose
¢ POLYSACCHARIDES
¢ Polysaccharides are produced when many monosaccharide units
are joined together by glycosidic linkage. Polysaccharides yield
more than 6 molecules of monosaccharides on hydrolysis .Some
polysaccharides are linear & others are highly branched.

Chemically, polysaccharides are of two types:

1. Homo polysaccharides / Homoglycans


¢ Which possess only one type of monosaccharides
¢ E.g., Starch, cellulose, glycogen

2. Hetero polysaccharides / Heteroglycans


¢ Which are formed by more than one type of monosaccharides

¢ E.g. Hyaluronic acid


¢ HOMOPOLYSACCHARIDE

STARCH :
¢ Starch contains only glucose residues & is found as a
storage carbohydrate in plants. Potato, wheat, rice, corn,
tapioca etc are some of the common food sources of
starch in our diet. It occurs as small granules with the
size range & appearance characteristics to each plant
species
¢ Starch is mainly used in foods to modify texture &
consistency, to bind H₂O, to thicken the foods & to form
soft spoonable gels. Natural starch is insoluble in water
& gives blue color when treated with iodine solution
¢ Starch consists of two forms: - The straight chain
polysaccharide called amylose, branched chain
polysaccharide called amylopectin. Most natural
starches are mixture of these two. Normally 65-85% of
starch is amylopectin and 15-35% is amylose
¢ AMYLOSE:
¢ It is a straight chain polysaccharide formed by 250-300
glucose residues, linked by α (1→4) glycosidic linkage.
Amylose is soluble in water and gives deep blue colour
with iodine. Amylose increases gel strength
¢
¢ AMYLOPECTIN:
¢ It is a highly branched polymer of glucose. In this
molecule branching occurs at intervals of 24-30
glucose residues. Glucose units of the main chain are
joined by α (1→4) glycosidic linkage (similar to amylose)
and the glucose units at the branch are joined by α
(1→6) glycosidic linkage to the main chain. It has about
3000- 6000 glucose units. It is insoluble in water.
Amylopectin with iodine gives red to violet colour.
Amylopectin decreases gel strength and viscosity
¢ Starch hydrolyzing enzymes:

¢ Hydrolysis of starch by enzymes give shorter chain of


glucose units called dextrins, maltose and finally D-
glucose
Starch → Dextrins → Maltose → D-glucose
¢ Dextrins are polysaccharides formed by partial hydrolysis
of starch
¢ There are different enzymes widely distributed in nature
react with starch mainly:-
¢ α -amylase:-
¢ α -amylase cleaves both amylose and amylopectin
molecules internally, producing oligosaccharides.
¢ β-amylase:
¢ They release the disaccharide maltose sequentially from
the non-reducing end of amylose & amylopectin, but it
cannot cleave 1→6 linkages at branch points. So we use
debranching enzymes like isoamylase and pullulanase.
These enzymes catalyse the hydrolysis of 1→6 linkages
in amylopectin producing numerous linear but low
molecular weight molecules
¢ GLYCOGEN

¢ It is the storage polysaccharide found in the muscle &


liver of animals & humans
¢ It is a branched polymer having about 8-10 glucose
units in each branch
¢ Each glycogen molecules may contain 5000-10,000
glucose units
¢ It is non-reducing, readily soluble in water & gives red
colour with iodine
¢ Like amylopectin, its straight chains are formed by alpha
1-4 glycosidic linkages & alpha 1-6 glycosidic linkages
exist at branch points
¢ It is similar to amylopectin in chemical structure but is
much more branched & of high molecular weight
¢ CELLULOSE
¢ It is the main constituent of plant cell walls

¢ It is a polymer of beta-glucose with beta 1-4 linkages b/w


glucose units
¢ This doesn’t occur in the animal body
¢ It is a homopolymer of glucose like starch, except the
linkages joining the glucose units are beta 1-4 rather
than alpha 1-4
¢ Strong hydrochloric acid hydrolyses cellulose to glucose

¢ Cellulose & its modified forms serve as dietary fiber


because they don’t contribute significant calories as they
pass through the human digestive system
Beta (1-4) glycosidic linkage in cellulose
¢ PECTIN
¢ It is found in fruits & vegs. & mainly prepared from waste
citrus peel & apple skin
¢ It is generally soluble in water & insoluble in most
organic solvents
¢ Pectins are mainly used as gelling agents ,but also acts
as a thickener, water binder & stabilizer
FOOD APPLICATIONS OF PECTIN
PRODUCT GROUP FUTN. OF PECTIN PCETIN LEVEL

Jam ,jellies & preserves Gelling agent, thickener 0.1 - 1.0

Bakery fillings & glazing Gelling agent, thickener 0.5 - 1.5

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Fruit preparations Thickener, stabilizer 0.1 - 1.0

Fruit beverages & Thickener, stabilizer 0.01 - 0.5


sauces

Confectionery Gelling agent, thickener 0.5 - 2.5

Dairy products Stabilizer, gelling agent 0.1 - 1.0


INULIN
¢ It is a starch found in tubers & roots
¢ It can be hydrolyzed to give fructose
¢ Inulin is a plant polysaccharide made up of
fructose , soluble in warm water & doesn’t
give any colour with iodine
¢ Inulins have sweet taste & are present in
many vegs. & fruits including onion, garlic,
bananas, asparagus etc
¢ Inulins are polymers consisting of fructose
units that typically have a terminal glucose
GUMS
¢ This large group of polysaccharides & their
derivatives is characterized by its ability to
give highly viscous solutions at low
concentrations
¢ Gums are widely used in the food industry
as gelling, stabilizing, & suspending agents
¢ This group include naturally occuring
compounds as well as their derivatives such
as exudate gums, seaweed gums, seed
gums, microbial gums etc.
SOME IMPORTANT GUMS
SOURCES GUMS
Algal polysaccharides Agar
Alginate
Carrageena

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n
Seed Gums Locust bean Gum
Guar gum
Tree exudate gums Gum arabic
Gum ghatti
Gum karaya
Gum tragacanth
Microbial Xanthan gum
polysaccharides Gellan Gum
SUMMARY

Carbohydrates
Conformations
Mono
Di
Poly

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