Carbohydrates

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Bio Chemistry
Quaid - e - Azam University Islamabad

CARBOHYDRATES

GROUP MEMBERS:
 MUNEEBAH NOOR
 UMM-E-KALSOOM (G.L)
 SHAZIA SULTAN
 MINAHIL ASLAM
 SADIA FATIMA
 KOMPAL FAYAZ

SEQUENCE:
INTRODUCTION 06-22
MONOSACCHARIDES 23-34
OLIGOSACCHARIDES 35-42
POLYSACCHARIDES 43-51
GLYCOCONJUGATE 52-61
APPLICATION & BIOINFORMAICS 62-73

Group of compounds composed of Carbon,
Hydrogen and Oxygen.
Polyhydroxy compounds of Aldehydes or Ketones.
Expressed by general formula Cx(H2O)y .
Synonymous to saccharide, meaning sugar.
Some common examples include: fructose(fruit
sugar), glucose(grape sugar), sucrose(cane sugar),
lactose(milk sugar).
INTRODUCTION:
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S O U R C E S
Most abundant of all biomolecules.
Widely distributed in plants and animals.
Synthesized by green plants during
photosynthesis.
Found in breads ,beans ,potatoes ,bran ,rice and
cereals.
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• Carbohydrate storage in the form
of glycogen provides energy.
• Supply carbon atoms for the
synthesis of other biochemical
substances(proteins, lipids and
nucleic acids)
• Linked to lipids, they are
structural part of cell membranes.
F U N C T I O N S
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Mouth
• (begins)chewing releases saliva containing
amylase enzyme
Stomach
• no enzymes, acid does some break down of
starch
Small intestine
Large intestine
D I E S T I O N
• majority of digestion takes place by pancreatic
amylase, maltase, sucrase and lactase.
• bacteria ferment some fibers
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BIOMEDICAL IMPORTANCE:
Brain cells and RBCs are wholly dependent on carbohydrates
for energy source.
• Precursors for many organic compounds(fats, amino
acids).
Participate in cellular functions.(cell growth, adhesion).
• Certain derivatives are used as drugs e.g.: cardiac
glycosides.
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CLINICAL CONCEPTS:
Glucose is most important energy source to
the mammals.
• Streptomycin is a glycoside used for treatment of
tuberculosis.
Mucopolysaccharide Heparin is a
polysaccharide , acts as an anticoagulant.
• Survival of Antarctic fish (below -2 C) is attributed to
antifreeze glycoproteins.
Mucopolysaccharide hyaluronic acid serves as
lubricant and shock absorbant for joints.
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TETSTS FOR DETECTION OF CARBOHYDRATES:
Molisch’s Test
Fehling’s Test
Benedict’s Test
Barfoed’s Test
Bial’s Test
Iodine Test
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M O L I S H ‘ S T E S T
INFERENCE:
Presence of
carbohydrates.
METHOD:
1ml test solution+2 drops of
alpha naphthol + mix + Add
conc. h2SO4 down the side to
form the ring at the interface of
two layers.
OBSERVATION:
Deep violet coloration at
junction of two layers
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F E H L I N G ‘ S T E S T
METHOD:
2ml of sugar
solution added to
2ml of Fehling's
solution and then
boiled for 10 mins.
OBSERVATIONS:
Red precipitation is
formed.
INFERENCE:
Presence of
reducing sugar.
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B E N E D I C T T E S T
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B A R F O E D R E A G E N T
INFERANCE:
Presence of
reducing sugars.
OBSERVATIONS:
Deep blue color
with red
precipitates settled
at bottom.
METHOD:
2 ml of test solution in 2ml
of Barfoed’s reagent. place
in boiling water bath and
heat for 3 mints then allow
to cool.
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B I A L ‘ S T E S T
METHOD:
3ml of bial’s
reagent to 0.2ml
of test solution .
Heat in water bath
for 3 mints
OBSERVATION:
Blue green or
muddy brown to
gray product.
INFERANCE:
Presence of
pentoses or
hexoses.
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I O D I N E T E S T
METHOD:
4-5 drops of iodine
solution added to 1ml of
test solution and
contents are mixed well.
INFERANCE:
Presence of
polysaccharide
OBSERVATION:
Blue color is
observed.
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REDUCING SUGARS NON-REDUCING SUGARS
Free aldehyde or ketone group. Aldehyde or ketone group utilized in bond
formation.
In hemiacetal or hemiketal form. In acetal or ketal form.
Do exhibit mutarotation. Do not exhibit mutarotation.
Do form oximes with hydroxylamine. Do not form oximes.
EXAMPLES: EXAMPLES:
glucose, fructose, lactose sucrose, glycogen , raffinose
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CLASSIFICATION:
Physiological
Classification :
on the basis of degree
of polymerization.
Chemical
Classification:
on the basis of
number of forming
units.
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Physiological Classification:
:
carbohydrates
Monosaccharides
Glucose
Fructose
Galactose
Disaccharides
Maltose
Sucrose
Lactose
Polysaccharides
Starch
Cellulose
Glycogen
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Chemical Classification:
carbohydrates
Simple
Monosaccharides
Glucose
Fructose
Galactose
Disaccharides
Maltose
Lactose
Sucrose
Complex
Polysaccharides
Starches
Fibers
Glycogen
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RAHCCASONOM SEDI
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Monosaccharides are a type of simple sugars or simple
carbohydrates
They are fundamental units of carbohydrates and cannot be
further hydrolyzed to simpler compounds
Monosaccharides come from Greek monos: single, sacchar:
sugar).
Their chemical formula: Cx(H2O)y, where conventionally x ≥ 3.
In structure one carbon is C==O grouped, others have OH
groups .Monosaccharides with aldehyde group (-CHO) is
Aldoses & with Ketone group (-C==O) is Ketoses`
INTRODUCTION:
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PropertiesColorless,
crystalline
Water
soluble
Sweet in
taste Building
blocks of
Disaccharides
If C>4, they
exist as a
Ring in
aqueous
solution
Reducing
sugars
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STRUCTURES:
STRAIGHT CHAIN: CYCLIC STRUCTURE:
D Glucose
an aldohexose
D Fructose
a ketohexose 726

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NOMENCLATURE:
 According to no. of carbons they contain in their backbone structure:
It is variable prefix followed by the suffix (-ose) (Trioses=3C),
(Tetroses=4C), (Pentoses=5C), (Hexoses=6C), (Heptoses=7C).
 According to nature of reactive group:
Aldoses sugar e.g. glyceraldehyde or a ketose sugar e.g.
dihydroxyacetone depending on the presence of Aldehyde and
Keto group .
 D & L- Isomerism:
The orientation of the –H and –OH groups around the
carbon atom adjacent to the terminal primary alcohol carbon
( as carbon 5 in glucose ) determines whether the sugar belongs
to the D or L series.
 When –OH is on the Right side the sugar is D isomer,
When it is on left, it is the L-Isomer.
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C L A S I F I C A T I O N
Trioses:
Glyceraldehyde
Dihydroxyacetone
Tetroses:
Erythrose, Threose.
Erythrulose
Pentoses:
Ribose , Arabinose
Ribulose, Xylulose
Hexoses:
Mannose, Glucose
Fructose, Psicose
BasedonNo.ofCARBONATOMS:
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E X A M P L E S
Glucose
Fructose
Ribose
Galactose
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An
Aldohexose
G L U C O S E
Key sugar of the body; Major source of
energy for the cell.
Compound of Disaccharides:
-Sucrose
-Maltose
-Lactose
Monomer of polysaccharides
-Starch
-Glycogen
-cellulose
found in candid soft drinks, sport drinks,
energy drinks, liquers, chocolate,
sweetened dairy products, desserts
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• Major constituent of
polysaccharides Inulin
• Found in honey, fruit juice,
high fructose corn syrup
(HFCS), agave nectar and
blackstrap molasses.
• Metabolize directly but is also
readily converted to glucose in
Liver.
F R U C T O S E
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AldoHexose
Isomer of Glucose
Can be found most readily
in Milk and Dairy products
G A L A C T O S E
Synthesis in the
Mammary Glands to
make the Lactose of
Milk
A constituent of
Glycolipids and
Glycoproteins in many cell
membranes such as those
in nervous tissue
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Ribose
Reducing
Sugar
Aldopentose
Ribose is
used in
RNA
Deoxy
Ribose is
used in
DNA
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Stereoisomers (same
atom connectivity,
different arrangement in
space)
Configurational
(separable)
Enantiomer
(stereoisomers that
are mirror images
of each other)
Diastereomers
(stereoisomers that
are not mirror
images)
Conformational
(related by rotation
around single bond.
Including chair &
boat conformation of
cyclic sugars )
Asymmetric Carbon Atom:
• Carbon atom that attached to 4
different groups.
• All monosaccharides have it
except dihydroxyacetone.
• Different isomers are possible
based on the presence of no. of
asymmetric carbon atoms.
STEREOISOMERISM:
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AHCCASOGILO SEDIR
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An oligosaccharide ") is a saccharide polymer containing
a small number (typically three to ten) of monosaccharides
Word derive from the Greek oligos, "a few", and sacchar,
"sugar")
INTRODUCTION:
Dietary
Oligosaccharides:
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Disaccharides:
Maltose (Glucose + Glucose)
Lactose (Glucose + Galactose)
Sucrose (Glucose + Fructose)
Trisaccharides:
Raffinose (Glucose + Fructose + Galactose)
Tetra saccharides:
Stachyose (2 Galactose + Glucose + Fructose)
Penta saccharides:
Verbascose (3 Galactose + Glucose + Fructose)
Glycoproteins
(oligosaccharides
+ Proteins)
Glycolipids
(oligosacchar-
ides + Lipids)
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D I S A C C H A R I D E S
(Double sugar or bios) formed by
Glycosidic linkage of two
monosaccharides i.e. α or β
(1,4;1,1;1,2;1,3;1,6)
The joining of simple sugars into a
double sugar happens by
a condensation reaction.
Hydrolysis with the help of a type
of enzyme called a disaccharidase.
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S U C R O S E
α(1→2) linkage b/w
glucose & fructose
Non-reducing ,
Produce naturally
from plant.
Melt at high
temperature,
decompose at 186°C
Digested by the
enzyme invertase, &
absorb into bloodstream.
Flavor for food and
medicines.
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M A L T O S E
Two glucose molecules
linked by α(1→4) bond
Broken down by maltase
enzymes into glucose
residue
30-60% as sweet as sugar,
Present in sweet potato,
cereals, turnips, low-fat
caramel sauce, pears
Maltobi-
ose or
malt
sugar
Reduc-
ing
sugar
• Controls the
growth of
microbes
• Extending
shelf life of
various foods
APPLICATIONS:
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β-1→4 glycosidic linkage b/w
glucose & galactose.
Digest by enzyme lactase (β-
D-galactosidase) in Villi.
Makes up around 2-8% of the
solids in milk
L A C T O S E
-Lactulose constipation
treatment.
-Flavours, stabiliser of
aromas and
pharmaceutical products.
β-D-
galactopyranosyl
- Reducing sugar
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C E L L B I O S E
 Reducing Sugar
β(1→4) bond b/w two β-
glucose molecules.
Hydrolysed to glucose with an acid.
Obtained by enzymatic or acidic
hydrolysis of cellulose (cotton, or paper)
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RAHCCASYLOP SEDI
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Poly means : “many”. & Saccharide means :
“sugar “ .
Complex polymer of monosaccharides joined by
Glycosidic Linkage
Their Chemical formula is Cx(H2O)y.
On hydrolysis, Give monosaccharide or
oligosaccharides.
Also called as a GLYCANS
INTRODUCTION:
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CLASSIFICATION:
Homo-polysaccharides
 Abundant in nature.
 Same kind of polymers.
 Branched and unbranched.
 Examples: Starch , glycogen
,cellulose and chitin.
Hetero-polysaccharides
 High molecular weight.
 Two monomer unbranched.
 Multiple monomer branched.
Examples:
• GAGs (the principle
component of proteoglycans) .
• Murein (bacterial cell wall).
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S T A R C H
• Soft and tasteless powder.
• Insoluble in cold water, alcohol , or other solvents.
• Their chemical formula is (C6H10O5)n -(H2O)
• Most abundant biomolecule on Earth.
• Reserved in plant tubers &seed endosperm.
AMYLOPECTIN
α1,4-glycosidic bond
with branch α
Insoluble in H2O.
1,6-glyco. Bond,
Branched.
AMYLOSE:
Soluble in H2O,
α 1,4-glycosidic
bond,
Unbranched.
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G L Y C O G N
1.Multibranche
d
polysaccharide.
2. Form of “energy
storage”.
2.Similar to
amylopectin.
3. Linked by alpha
acetal bond
4.Also called As “
Animal Starch”
5.In humans,
animals ,fungi and
bacteria.
6.Formula :
(C6H1OO5)n
.
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C E L L U L O S E
1. Most abundant Linear
polymer.
2.Component of plant
cell wall.
•3. Source of energy as
breakdowns into glucose
residue
4.Beta 1,4-
glycosidic
bond
&
Hydrogen
bonds.
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C H I T I N
Cell wall
component. Also
present In fungi,
arthropods and
insects.
Complex polymer.
Manage
cholesterol level.
USES:
Food additive.
Emulsifying
agent.
Surgical thread
Making fertilizers.
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GAGs (high molecular weight):
Most abundant
hetero-
polysaccharide.
Long and
unbranch
ed.
Repeating
disacchari
de units.
Highly
negatively
charged.
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Murein (peptidoglycan):
Contain sugar
and amino acids.
Forms a “mesh
like layer”
outside plasma
membrane .Some archea
have similar layer
of pseudo-
peptidoglycans.
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ETAGUJNOCOCYLG
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Carbohydrates
covalently linked
with proteins,
peptides and lipids.
Formed by the
process known as
glycosylation.
They involve in
biological processes
such as cell-cell
recognition, immune
response, wound
healing and
detoxification.
I N T R O D U C T I O N
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Classified into three
groups
Glycoprotein
Proteoglycan
Glycolipid
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G L Y C O P R O T E I N
Oligosaccharides attached covalently to protein.
Proteins are present in more amount by mass as
compared to oligosaccharides.
They are formed by the process of glycosylation.
Found in outer face of plasma membrane, in the
extracellular matrix and cellular organelles such as
golgi-complex, secretory granules and lysosomes
etc.
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N-Linked Glycosylation:
Sugar is attached through a N- glycosidic
bond to asparagine residue of protein
Found in ovalbumin and immunoglobin
O-Linked Glycosylation:
Sugar is attached to polypeptide chain
through hydroxyl group of amino acid
serine or threonine .
Found in antifreeze glycoprotein and
blood group antigens
GLYCOSYLATION:
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EPO
• Erythropoetin , a
hormone consisting of
193 amino acid &
molecular weight of
34000
• Highly glycosylated
and responsible for
the production of
RBCs
Fibrinogen
• Glycoprotein in
vertebrates , helps in
the formation of
Blood clots
• These polypeptides
are linked together by
29 disulphide bond
Transferin
• Iron-binding Blood
plasma glycoprotein
• Control the level of
free iron in biological
fluids
E X A M P E L S
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P R O T E O G L Y C A N
Glycosaminoglycan(GAG) chains joined covalently to
membrane protein or a secreted protein.
GAGs are present in greater fraction.
Found on cell surface or extracellular matrix of the
cell
Major components of connective tissue such as
cartilage.
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Syndecans
• Family of
transmembrane
proteoglycan .
• Perform multiple
function during
damage repair,
development etc
Glypicans
• Heparin sulphate
proteoglycan
• Involved in growth
factor signalling
Hhs(Hedgehogs),
FGF(Fibroblast
Growth Factor),
BMP(Bone
morphogenic
protein).
Aggrecans
• Contain three
globular domains G1,
G2, G3
• Component of
cartilage structure
and function of joints
E X A M P E L S
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G L Y C O L I P I D S
Oligosaccharides attached covalently to
lipids.
Called membrane lipids and are mainly found
on the surface of membrane
Role: maintain the stability of cell membrane
and to facilitate cellular recognition.
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Cerebrosides
• Glycolipids having galactose as
the main sugar
• abundant in the myelin sheath
of nerves and white matter of
brain
Gangliosides
• They contain N-acetyl
glucosamine besides other
compounds
• Involved in the ion-transport
and form receptor for viral
particle and toxin
E X A M P E L S
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SESAESID
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It is an inborn
error of
metabolism when
body is unable to
break galactose
There is a
deficiency of
enzyme galactose -
3-
phosohateuridyltra
nsferace.
Due to block of
enzyme galactose -
3-phosphate will
accumulate in cells
.
ETIOLOG
Y: Clinical
manifestation
including
congenital cataract
and presence of
galactose in urine
as well
Elevated glucose
level will help in
diagnosis
DIAGNOS
IS:
If lactose is
withdrawn from
the diet most of the
symptoms recede.
TREATME
NT:
GALACTOSEMIA:
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MILK
In the body, Lactose is split into
glucose & Galactose
Used for energy
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HYPOGLYCAEMIA:
ETIOLOGY:
• When the
blood glucose
concentration
falls to less
than 45mg/dl
the symptoms
of
hypoglycaemi
a appears.
SYMPTOMS:
• Headache
• Anxiety
• Confusion
• Sweating
• Slurred
speech
• Seizure
• Comma
CAUSES:
• Alcohol
intake
• Insulin
overdose
• Premature
infants
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DIABETES MELLITUS:
ETIOLOGY:
• It is a condition in which blood glucose level is much
higher than normal . Hence the condition is also
commonly known as sugar disease.
TYPES:
• IDDM
• NIDDM
DIAGNOSIS:
• Diagnosis of diabetes made on basis of individual
response to oral glucose load ,oral glucose test(OCTT).
MANAGEMENT:
Dietary management
Hypoglycaemia
Insulin
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TYPES:
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SYMPTOMS:
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Bioinformatic Applications of Carbohydrates
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Simplified representation of
complex structure are used to code
information
Full names and short codes for
common monosaccharides and
derivatives have been defined e.g
Glu for glucose
Tools are developed for computer
representation.
Graphical representation of carbohydrates structure
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Data bases and tools for glycobiology
Variety of databases are available to the glycoscientist.
I.Glycoproteins databases are of two kinds
II.I- Databases that contain information on protein
III.II- Databases that show information on protein and in
enzymes .
Primary Database: Direct experimental results.
Secondary Database: Result of analysis on primary database
SEQUENCE
LIPIDS , CARBOHYDRATE
GENOME
LITRATURE
PATHWAYS
STRUCTURE
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Carbohydrates 3D structure and molecular modelling
MD simulation of
carbohydrates are
most popular
method in
modelling of
carbohydrates 3D
structure.
Quantum
mechanics method
are used for
modelling of
carbohydrates
conformation
These are used to
study chemical
reaction
For conformational
analysis of smaller
carbohydrates
3D structure of Glucose
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Thank You

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WE ARE
HERE TO
ANSWER
YOU!!
QUESTIONS
PLEASE!!!!!

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References:
 Oligosaccharides at the US National Library of Medicine Medical Subject Headings(MeSH)
 Walstra P, Wouters JT, Geurts TJ (2008). Dairy Science and Technology (second ed.). CRC, Taylor & Francis.
 Whitney E, Rolfes SR (2008). Understanding Nutrition (Eleventh ed.). Thomson Wadsworth.
 Fundamentals of Biochemistry: Life at the Molecular Level (4th ed.).
 Varki A (ed.). Essentials of Glycobiology (2nd ed.). Cold Spring Harbor Laboratories Press.
 Biose on www.merriam-webster.org
 Compendium of Chemical Terminology (1997). Online corrected version: (2006) "disaccharides".
 Biology- A course for O Level. p. 59.
 Whitney, Ellie; Sharon Rady Rolfes (2011). Peggy Williams, ed. Understanding Nutrition (Twelfth ed.). California: Wadsworth, Cengage Learning. p. 100.
 William Allen Miller (1857). Elements of Chemistry: Theoretical and Practical, Part III. Organic Chemistry; pages 52 and 57
 Hyvonen, L. & Koivistoinen, P (1982). "Fructose in Food Systems". In Birch, G.G. & Parker, K.J. Nutritive Sweeteners. London & New Jersey: Applied
Science Publishers. pp. 133–144.
 J. Modric, "Monosaccharides or Simple Sugars," [Online]. Available: http://www.nutrientsreview.com/carbs/monosaccharideS
 "Biology Dictionary," [Online]. Available: https://biologydictionary.net/monosaccharide/. [Accessed 04 07 2018].
 P. H. Jakubowski, "Biology, Libre texts," [Online]. Available:
https://bio.libretexts.org/TextMaps/Biochemistry/Book%3A_Biochemistry_Online_(Jakubowski)/03%3A_CARBOHYDRATES%2F%2FGLYCANS/A._Monos
accharaides_and_Disaccharides/A2._Monosaccharide_Isomers. [Accessed 06 07 2018].

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