CARBOHYDRATES
CHEMISTRYOF
10
" " " "
teropolysaccharides significance
To their functions
(GAGs).physiological To carbohydrates
classification
To of To
know know know learn
the the
objectives
learning
Specific
ofthe biomedical
features types mono,
physical
of
diimportance,
homopolysaccharides
and and and
definitionand
chemical
general polysaccharides
functions
properties
and
and
FUNCTIONS OF CARBOHYDRATE
1.Chief source of energy in the body. Brain cells & RBCS are
DEFINITION completely dependent on carbohydrate as energy source
(4kcal/gm) ’ Glucose
2. Storage form of energy in plant (Starch ) &
Carbohydrates are defined as poly hydroxy animal ( Glycogen)
derivatives of aldehydes or ketones or 3. Excess carbohydrates are converted to fat & stored in
compounds which yield these on hydrolysis
adipose tissue
4. Components of cell membrane (Glycocaly) e.g.
General formula: (CH,0), Glycolipids, Glycoproteins
5. Serves as structural components (e.g. GAGs as ground
substance in higher organism)
CLASSIFICATION OF CARBOHYDRATE
6.Non digestible carbohydrates like cellulose 1. Monosaccharides:- e.g. Glucose, Fructose
serves as dietary fibers l.e. it forms bulky stools Molecule having only one sugar group and cannot be hydrolyzed further Into
smaller unlts
& prevents constipation
7.Ribose &deoxyribose sugars are part of the 2. Disaccharides: e.g. Lactose, Maltose Glycosidic bond
t consist of 2 monosaccharlde units Jolned by glycosldic bonds
structural framework of RNA and DNA
respectively. 3. Oligosaccharides: 3-10 monosaccharides
8.Carbohydrate act as precursors for other organic 4. Polysaccharides:
compounds like lipids and amino acids. a)Homopolysaccharides: e.g. glycogen, starch
9.Play role in cell growth, cell to cell recognition, GLU GLU GLU GLU GLU
interaction & adhesion.
b) Heteropolysaccharides: e.g. chondroitin, heparin
Amino Uronkc Amino Uronke Amino
4 SUar acid acid suar
MONOSACCHARIDES MONOSACCHARIDES
" Molecule having only one sugar group and " Molecule having only one sugar group and cannot be hydrolyzed
further into smaller units, called as simpler sugar e.g. Glucose.
cannot be hydrolyzed further into smaller units, " Subdivided as follows
called as simpler sugar e.g. Glucose. 1. Depending on functional group
Subdivided as follows e.g. Aldoses: Glucose, Galactose
ketoses: Fructose
1. Depending on functionalgroup 2. Depending on number of carbon atoms
e.g. Aldoses : Glucose, Galactose Aldoses Ketoses
ketoses: Fructose Trioses Glyceraldehyde Dlhydroxy acetone
Erythrose
2. Depending on number of carbon atoms: Tetroses
Ribose, Xylose
Erytrulose
|Pentoses Ribulose,Xylulose
Trioses, tetroses, pentoses & hexoses etc. Glucose, Galactose
|Hexoses Fructose
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IMPORTANCE OF MONOSACCHARIDE
Sugar SOurce Biochemical Importance Clinical significance
ISOMERS
Frults, Julces, Compounds Possessing identical molecular formula but
ydrolysis of Excreted In the urine
different structures are called as Isomers.
Glucose ne main metabolic fuel for (glycosuria) in poorv
starch. Cane or beet issues,
sUgar, maltose and "blood surar controlled dlabetes mellitus as
a result of hyperglycemla
lactose
Readily metabolized via Hereditary fructose
glucose or directly Intolerance leads to fructose
Fructose Fruits accumulation and
Energy source for sperm ln
semen hypoglycemla
Readily metabolized to
Hydrolysls of glucose.A constltuent of Hereditary Galactosemia
Galactose
lactose ycoliplds sand Cataract
glyc roteins
Nucdelc acds and
Structural component of nuclelc acids and coenzymes,
Ribose metabolic
Intermedlate
Including ATP, NAD(P), and flavin coenzymes
Hydrolysts of plant Constituent of mucoprotelns and glycoprotelns
Mannose manan gums
Structural Isomers -Same molecular " Structural Isomers
formula but differ in structure Citrate CH,COOH
HO C COOH
Eg. C,Hi2 CH, COOH
nPentane CH,CH,CH,CH,CH,A Isocitrate
HO CH COOH
CH COOH
IsoPentane CH,IWKACYSb Ho CH,COOH
SCH CH,CH,
CH,
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" Stereo lsomers : Same molecular formula, . ieometrical 0Nomerism -Cis trans isomnerisn Differ in
but differ in the spatial configuration of spatialconliguration of atoms around a double
substituent groups. bonded C atom.
HC COOH HC COOH
HC COOH
2 Types- Geometric isomers Maleic acid Fumaric acid
Optical isomers
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Optical isomers - (Configurational) differ from Compounds having same structural fornula but differ in
disposition of various atoms or groups in space around an spatialconfiguration are known as stereoisonners:
asymmetric Carbon atom (Chiral center)
An asymmetric Carbon atom is a Carbon atom the four valences
of which is attached to four different atoms or groups of atoms.
M Asymmetric carbon means that
four different groups are
N-C-P attached to the same carbon.
The reference molecule is glyceraldehyde which has a single
asymmetric carbon atom.
Optical Activity:
H-¢-OH
1
H-o When a beam of plane-polarised light is passed through a
2
HOH solution of carbohydrates,
HO-H 3
H-¢OH it will rotate the light either to right or to left.
HO-¢-H
H--OH dextrorotatory (+) (d)
HOKSe or levorotatory(-) ()
6 H,-OH
H,-OH
D-glucose (natural) Lglucose
Penultimate (reference) carbon atom
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EPIMERS REDUCING PROPERTY OF SUGAR
" Isomers differ from each other in their configuration (REDUCING SUGAR)
around single carbon atom, are referred as epimers.
" Biologically most important epmer of glucose is galactose " Sugars containing free aldehyde or ketone
at C-4
group are called as reducing sugars.
Group of enzymes catalyses tis reaction named as
epimerases " e.g. Glucose, fructose, galactose, maltose,
lactose
0H
4-OH HOH Tests performed to detect reducing property:
-OH Benedict's test
CH,OH CHOH
Dgalactose
Dgucose
ENEDIOL FORMATION:
Sugars treated with alkali forms enediols.
Chemical properties
REDUCTION REACTION
" Enediols are highly reactive compounds.
" Principle of Benedict's test: (based on reducing property) " Sugar with reducing agents/enzymes form
corresponding alcohol.
allali " e.g
Sugar Enediols Cuz (copper sulphate)
1. GlucOse Sorbitol
oxidised reduced
2. Galactose > Galactitol
Sugar acid Cut ’ 2Cu(OH) Cu,o
yellow Red 3. Mannose Mannitol
This test is used to detect presence glucose in urine (glycosuria) 4. Fructose Sorbitol/mannitol
" Semiquantitative tests : depending on color of precipitate.
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Clinical Importance: GLYCOSIDE FORMATION
" The osmotic effect of sorbitol and galactitol
produces changes in tissues when they Glycosides are formed from condensation
accumulate in abnormal amounts e.g. Cataract between a monosaccharide & monosaccharide or
of lens. other compound (aglycone)
" Mannitol is used to reduce intracranial
pressure by forced diuresis.
ClinicallyImportant glycosides: AMINO SUGARS
1) Sugar + sterold (aglycone) ’ Digoxin Amino sugars are obtained by replacing hydroxyl(OH)
group of monosaccharide by amino group
"Cardlac glycosides, digoxin Increases heart muscde " Most common examples are
contractlon & used for treatment of congestlve heart 1. D-Glucosamine
fallure. 2. D-Galactosamine
CHO
2) Antlbiotlcs - Streptomycin , erythromycin.
3) Glucose + Phloretin ’> Phlorhlzin ’ renal damage
4) Phlorhizin, an Inhibltor of sodium dependent co
transport of glucose > glycosurlaUse: Experimental Glucosamine N-acetyl glucosamine
dlabetes In rat
Occurrence: Important constituent of
Glycosaminoglycans(GAGS) and Glycoproteins.
IMPORTANCE OF DISACCHARIDE
DISACCHARIDES
NameSourceCompositlon Importance
" It conslst of 2 monosaccharide units joined by
glycosidic bonds Cane Glucose+ Commonly used as table
Sucrose
sugar Fructose sugar
The physiologlcally important disaccharides are,
Glucose+ Glucose Exclusive sugar for breastfed
1. Maltose Glucose +
infants. Lactase enzyme
Glucose+ Fructose Lactose Milk Galactose
deficiency leads to lactose
2. Sucrose
intolerance
3. Lactose
Glucose+Galactose
Malt Glucose+ |Important intermediate in
Malitose produ Glucose
starch digestion
cts
POLYSACCHARIDES Homopolysaccharides
Polysaccharides known as glycans, contain more than |1)Starch- It is a storage form of carbohydrate in
10monosaccharide units joined by glycosidic linkage. plant
They may be classified as, |2) Glycogen- Storage form of glucose in animals
1. Homopolysaccharides /Homoglycans: (liver & muscles)
contains only one type of monosaccharide units 3) Cellulose- Cellulose is the chief constituent of the
e.g starch, glycogen, Inulln, cellulose framework of plants. Found in bran, flour, and
tubers.
2. Heteropolysaccharides /Heteroglycans:
composed of different types of monosaccharides or their It is a non digestible polysaccharide in human
derlvatives being & thus prevents constipation.
e.g. GAGS (Glycosaminoglycans)
GLYCOGEN
STARCH
It is a storage form of carbohydrate in plant " Storage form of glucose in animals (liver &muscles)
The two chief constituents of starch are amylose &amylopectin
It is a branched polysaccharide of glucose &contains
a(1-4) &a(1-6) (at branch point) linkages
" Anylose made up of glucose unit with a(1-4) linkage is the In muscles serves as energy reserve for muscle
soluble part
" Has low glycemic index contraction whereas liver glycogen contributes glucose
" Amylopectin made up of glucose unit with a(1-6) linkage, but to maintain blood glucose level
highly branched, is the insoluble part d
"Has high glycemlc
Starch is non reducing sugar forms blue color with lodine test
Degradative product of starch hydrolysis
Starch camyase dextrin Maltose
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at branch aine
DEXTRAN CELLULOSE
Highly branched homopolymer of glucose with a 1-4, 1-6 and
1-3 linkages. " Cellulose is the chief constituent of the framework of plants
Produced by micro-organisms
Since they will not easily go out of vascular compartment, so " Found in bran, flour, and tubors.
are used for intravenous infusion as plasma volume expander
for treatment of hypovolemic shock " It has straight line structure made up of glucose molecules
Dextrans are different from dextrins with B(1-4) linkage, without branching points.
INULIN " Amylase can break a (1-4) linkage present in starch but
" Inulin is polysaccharide made up of D-Fructose units with B1-2 cannot break B(1-4) linkage of cellulose.
linkage
" So it is a non digestible polysaccharide in human being.
It is the reserve carbohydrate present in various bulbs and
tubors such as onion, garlic and chickory Contributes bulk to the stools & assists in bowel movements
Clinically used to measure GFR by calculating clearance value
thus prevents constipation.
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HETEROPOLYSACCHARIDES
Hyaluronic acid
Mucopolysaccharides/ Glycosaminoglycans(GAGS):
Core protein
Features:- GAGS made up of following components Keratan sulphate
One component of which is always an amino sugar
(glucosamine or galactosamine)
Other component is uronic acid (glucuronic acid/
iduronic acid) Chondroitin
sulphate
These GAGS attached to extracellular protein called core
protein to form proteoglycans
Name Composition Location Functions
Occurrence: GAGs are found in the: 1)Lubrlcant &
1. Synovlal fluld
Hyaluronlc Glucuronic Ground
Acid Acid +N-Acetyl Substance of Shock absorbent
2. Vitreous humour of the eye Glucosamine Connective in jolnts due to
3. Arterial walls highly viscous
tissue,
4. Bones Vitreous nature
5. Cartilage humor of eye,
Synovial fluid 2) Acts as
General functions: of joints cementing
extracellular material and
1. They are major components of the contributes
matrix or ground substance.
elasticity and
matrix, which
2. GAGs imbibe water & form gel like shock.
tensile strength
functions as cushion against mechanical to cartilage and
tendons. 47
3. Prevent blood clotting e.g Heparin.
Name Composition Location Functions Name Composition Location Functions
Heparin Glucuronic acid Arteries of 1) Prevent Chondroitin Glucuroníc Cartilage, 1) Principal
Tiduronic acid Liver, Lungs, Blood Sulphates Acid +Nacetyl bones, GAGS of cartilage
Galactosamine Cornea etc where it binds
+ Spleen Clotting.
Glucosamine 2) Helps in + Sulphate collagen and
+sulphate release of holds fibers in
Lipoprotein a strong &
Lipase tight way.
(Clearing of Galactose + For Corneal
Keratan Cornea,
Lipemic Cartilage Transparency
plasma) Sulphate NAcetyl
|Glucosamine
Dermatan lduronic acid + Skin,Tendons Role in corneal + Sulphate
|Sulphate N-acetyl Cornea, transparency
Galactosamine Heart valves, and shape of
+ Sulphate sclera eye
Nutritional importance - Dietary Fibers Functions:
" Defined as the non-digestible complex carbohydrates having 1. Action on bowel motility: Can absorb large amount of water
varying degree of solubility present in plant cell components. because of hydrophilic nature, increasing bulk of stools and bowel
motility promoting normal laxation.
" Soluble fiber is the part which is not digested by human enzymes
in small intestine, but in large intestine it is broken down by the Use: To relive constipation.
bacteria.
2. Cholesterol lowering effect: Fibers combine with cholesterol and
e.g. pectins and gums
eliminate it feces, so as to lower plasma cholesterol concentration.
"Insoluble fibers passes through the digestive tract largely intact Use: To treat hypercholesterolemia
e.g. cellulose and lignin
"Dietary fiber provides little energy but has several beneficial 3. Anti-hyperglycemic effect: Fibers form a vicious gel in stomach
effects and intestine to slow the rate of digestion and absorption of
carbohydrates. Thus the sudden rise in blood glucose is prevented.
"Dietary source: Cellulose- bran, flour, tubers
Pectins- Fruits like apple and berries Use: High fiber diet for patients of diabetes mellitus.
Gums- Legumes and oat meals
4. Elimination of toxic compounds: fibers can Glycemic index
bind various toxic compounds The glycemic index (GI) is a number associated with
including particular food that indicates its effect on a person's blood
certain carcinogens and bacterial toxins and glucose level.
eliminate them through fecal route.
" High GI foods: Bread, potatoes, table sugar
5. Satlety effect: Fibres significantly increase " Low GI foods: Legumes, whole grain, cereals
bulk of diet getting a feeling of fullness
" Useful in formulating therapeutic diets for diabetic patients
without consumption of exXcess calories, so
recommended in obesity. Foods with low glycemic index are favored in diabetic diet,
because they prevent steep rise in blood sugar conc. after each
meal.
Common sugar substitutes
" Aspartame:
" is made from aspartic acid and phenylalanine.
" It is 200 times sweeter than sugar
" Not indicated to patients with PKU.
" Saccharin:
" Made from anthranilic acid
THANK YOU.
300 times sweeter than sugar
" Calorie content in NIL
Cyclamate:
30-50 times sweeter than sugar
so banned in most of the countries
" It can cause bladder cancer,
several times sweeter than
" Stevia: Extract of leaves of plant stevia is
sucrose.
carbohydrates.
Applications: DM, Persons on dietary restrictions of S4
