Carbohydrates

Life’s
Sweet Molecules
Contents:
• Introduction
• Defnition
• Functions
• Physical properties
• Classification
• Chemical properties
• Polysaccharides
• Starch- gelatinization, retrogradation, hydrolysis
• Other plant polysaccharides
• Microbial polysaccharides
 Introduction:
• Organic compounds composed of Carbon, Hydrogen
and oxygen and they are often called as sugars.
• Many Carbohydrates also contain Nitrogen and other
elements.
• Carbohydrates comprise more than 90% of the dry
matter of plants.
• They are abundant, widely available, and inexpensive.
• They are common components of foods, both as
natural components and as added ingredients.
• They have many different molecular structures, sizes,
and shapes and exhibit a variety of chemical and
physical properties.
 Defnition:
• Carbohydrates are polyhydroxy alcohols with
potentially active carbonyl groups which may be either
an aldehyde or ketone group.
• General formula: (CH2O)n
Functions:
• Energy reserves (e.g., Starch, fructans, glycogen).
• Structural materials (Cellulose, Chitin).
• Important component of cellwall (glycoprotein,
glycolipids).
• Important component of nucleic acids (ribose and
de-oxy ribose).
• Protein sparing action.
Physical properties:
• Solubillity: Monosaccharides tend to be soluble in
polar solvent; they are also soluble to a small
extent in ethanol but not soluble in organic
solvents such as benzene, chloroform, and ether
• Hygroscopicity: Sugar in crystallized form has the
ability of moisture uptake.
• sugars are crystalline compounds and sweet to
taste,soluble in water and it forms true solutions.
• The polysaccharides are tasteless and amorphous
compound,insoluble in water and it forms colloidal
solutions.
• Amphoteric in nature.
Clasification:
They are classified according to their molecular
structure into 3 main categories viz.,
1. Low molecular weight mono and disaccharides.
2. Intermediate molecular weight oligosaccharides.
3. High molecular weight polysaccharides.
Monosaccharides:
• Monosaccharides are the simplest carbohydrates.
They cannot be broken down to smaller
carbohydrates.
• These monosaccharides are divided into 2 major
groups based on functional group present.
1) Aldoses: presence of aldehyde as functional
group. E.g., glucose
2) ketoses: presence of ketone as functional group.
E.g., fructose
• These monosaccharides are inturn classified
according to the number of carbon atom present in
chain as;
1. Trioses (C3) : Glcceraldehyde
2. Tetrose (C4) : Erythrose,
3. Pentoses (C5) : Ribose, arabinose
4. Hexoses (C6) : Glucose
5. Heptoses (C7) : Sedoheptulose
Disaccharides:
• Disaccharides consist of two monosaccharide units
joined together; they can be split into two
monosaccharides.
• e.g.,sucrose, lactose, maltose
• Sucrose = glucose + fructose
• Lactose = glucose + galactose
• Maltose = glucose + glucose
Oligosaccharides:
• Oligosaccharides contain anywhere from three to
ten monosaccharide units.
• E.g., Trisaccharide: Raffinose,
Tetrasaccharide: Stachyose
Polysaccaharides:
• A polysaccharide consists of many monosaccharide
units i,e., more than 10 monosaccharide units
bonded together through glycosidic bonds. They are
classified as ;
1. Homopolysaccahrides: Starch, glycogen, cellulose.
2. Heteropolysaccharides: Agar, mucopolysaccharides
Chemical properties of cabohydrates

Oxidation and Reduction Reactions:

• Oxidation and reduction reactions are commonly called
redox reactions.
• Oxidation is a loss of electrons.
• Reduction is a gain of electrons.
• An aldehyde functional group can undergo oxidation by
gaining oxygen or it can undergo reduction by gaining
hydrogen.
• In monosaccharides, oxidation produces a sugar acid, and
reduction produces a sugar alcohol.
Oxidation:
An aldehyde functional group can undergo oxidation by
gaining oxygen or loosing hydrogen and during oxidation,
aldehydes form carboxylic acids
Reduction:
An aldehyde functional group can can undergo
reduction by gaining hydrogen or loosing oxygen and
and during reduction, they form alcohols.
Condensation and hydrolysis
• The –OH group that is most reactive in a
monosaccharide is the one on the anomeric carbon.
• Condensation is the formation of glycosidic bonds.
• Hydrolysis is the breakdown of glycosidic bonds.
condensation:
• Condensation reaction is a type of reaction that
occurs when two molecules are joined and a water
molecule is produced. This type of reaction is referred
to as a dehydration reaction.
• When this hydroxyl group reacts with another hydroxyl
group on another monosaccharide a glycosidic bond
is formed.
Hydrolysis:
• Hydrolysis reaction is the reverse of a
condensation reaction. A larger molecule forms
two smaller molecules and water is consumed
as a reactant.
Formation of amino sugars:
• Substitution of Amino Group for a Hydroxyl Group
of a Sugar Results in the Formation of an Amino
Sugar.
• E.g., glucosamine, galactoseamine
 Formation of sugar
phosphates
• Phosphates of Glucose, Fructose and
Glyceraldehyde etc. are important intermediate
compounds in carbohydrate metabolism of almost
all the cells.
• E.g., Ribose and Deoxyribose in Nucleic Acids are
Phosphate Esters of these monosaccharides.
Browning reactions:
Non-enzymatic browning:
1. Maillard Reaction: was first observed by the
French chemist Louis-Camille Maillard. (1912)
after heating a solution containing glucose and
lysine.
• When amino acid reacts with reducing sugars a
series of complex reactions, referred as the
Maillard reactions, occurs, leading to formation of
flavors, aromas, and dark colored pigments.
• These reactions may be desirable or undesirable.
• Sometimes it is toxic and causes mutation.
2. Caramelization: Degradation of sugars during
heating.
• Heating of both reducing (e.g., glucose) and
nonreducing sugars (e.g., sucrose) without any
nitrogenous compounds results in a complex group
of reactions leading to a dark brown caramel.
• It is used in colas and other soft drinks, baked
goods, candies, and other food products as a
colorant and flavor compound.
• Reaction is facilitated by the presence of an acid,
base, or salt.
 Polysaccharides:
• Glycan is a common term used for polysaccharides.
• Polysaccharides are high molecular weight carbohydrates.
• Polysaccharides are polymers of monosaccharides bonded
together through glycosidic bonds.
• Homopolysaccharide: starch, glycogen, cellulose
• Heteropolysaccharide: Agar, mucopolysaccharide
Sources of Polysaccharide:
• Microbial fermentation
• Higher plants
• seeds
• tree extrudates
• marine plants
• Chemical modification of other polymers
Starch:
• It is a storage polysaccharide present in plants.
• Source: normal corn, waxycorn (waxy maize), high-
amylose corn, wheat, and various rices, and from
tubers and roots(potato and cassava).
• Starch consists of amylose, a linear chain of
glucose, and amylopectin, a branched chain of
glucose.
• Food uses of starch includes adhesive, binding,film
forming, foam gelling, strengthening, glazing,
moisture retaining, stabilizing, texturizing, and
thickening agent.
 Gelatinization
: starch gelatinization is the process where starch and
water are subjected to heat causing the starch
granules to swell.
• As a result, the water is gradually absorbed in an
irreversible manner. This gives the system a viscous
and transparent texture. The result of the reaction
is a gel, which is used in sauces, puddings, creams
and other food products, providing a pleasing
texture.
Retrogradation
• Starch retrogradation is a process in which
disaggregated amylose and amylopectin chains in a
gelatinized starch paste reassociate to form more
ordered structures.
Factors affecting retrogradation:
i. Size of linear starch molecule.
ii. Amylose/amylopectin ratio.
iii. Rate of cooling.
Hydrolysis of starch:
• Starch molecules, like all other polysaccharide
molecules, are depolymerized by hot acids or
enzymes results in breakdown of glycosidic bonds
and forms either monosaccharides, disaccharides
or trisaccharides.
• Functional Properties of Starch Hydrolysis Products:
Sweetness, Hygroscopicity and humectancy,Freezing
point depression, Flavor enhancement,
Fermentability, Browning reaction.
Pectin:
• Source: Cell walls of higher plants (citrus rind)
• Structure: Largely a linear polymer of
polygalacturonic acid with varying degrees of
methyl esterification.
• >50% esterified is a high methoxy (HM) pectin
• <50% esterified is a low methoxy (LM) pectin
• Functional Properties: High methoxy pectin will
gel in the presence of acid and high sugar
concentrations. Low methoxy pectin will gel in the
presence of calcium.
• Thickening and gelation of fruit pulp (jams, jellies),
gelation of jelly candies.
Algin:
• Source: Brown seaweed
• Structure: linear polysaccharide containing two types
of residue (i.e., a co-polymer): b-D-
mannopyranosyluronic acid and a-L-gulopyrasonic acid.
• Functional Properties: Viscous in aqueous solution,
gels in the presence of Ca2+ (or low pH). Gels are temp
stable.
• PGA (propylene glycol alginate)
• Used as a thickener in salad dressings, low-calorie
dressings, used in conjunction with xanthan.
Gum Arabic:
• Source: exudate of tree (acacia).
• Structure: heterogeneous material consists of two
fractions. One, polysaccharide chains with little or no
nitrogenous material other contains high molecular
weight proteins.
• Functional Properties: dissolves easily when stirred in
water, high solubility and the low viscosity, functions in
confections are to prevent sucrose crystallization.
• Used in Stabilization of protein foam in beer, whipped
cream, meringues, chocolate marshmallows.
Carageenan:
• Source: Red seaweed
• Structure: Linear D-galactopyranosyl chain with
alternating (1,3)-α-D- and (1, 4)-ß-D-glycosidic
linkages,
• Functional Properties: pH independent thickening,
melting, phase separation; improvement of
consistency
• k-carageenan in dairy foods
• Used in Stabilization of ice cream against ice crystal
formation,
Xanthan gum:
• Source: Product of bacteria Xanthomonas
campestris
• Structure: cellulose-like backbone (b-1,4-poly-
glucose) with trisaccharide branches (stubs) on
alternate monomers on the backbone carrying
carboxylic acid residue.
• Functional Properties: Water soluble, viscous,
non-gelling. Viscosity is only slightly temperature
dependant.
• It is widely used as a food gum, sauces, syrups and
toppings, and salad dressings.
other microbial polysaccahride
• Dextrans: L. mesenteroides
• Pullulan: fungus Aureobasidium
• Gellan: P. elodea
• Xylinan (Acetan): Gram-negative bacterium A.
xylinum
References:
• Fennemas food chemistry (4th edition)
• Food carbohydrates: chemistry, physical propertis
and applications (edited by STEWE W. CUI)
• Handbook of food chemistry (general properties of
major food components)
• Polysaccharide, microbial (Elsevier)