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Dr SHAZIA
DAWOOD
Carbohydrates
• Carbohydrates are the most abundant
organic molecules in nature.
• Hydrates of carbon
• Carbohydrates are defined as
polyhydroxyaldehydes or ketones or
compounds which produce them on hydrolysis.
• Composed of carbon, hydrogen and oxygen
• General molecular formula Cn (H2O)n
• Some carbohydrates contain Sulphur,
Nitrogen or Phosphorus
• Exceptions are acetic acid C2H4O2 and
lactic acid C3H6O3.
Functions of Carbohydrates
• Main sources of ENERGY in body (4kcal/g)
– RBCs and Brain cells have an absolute
requirement of carbohydrates.
• Storage form of energy (starch and glycogen)
• Excess carbohydrate is converted to fat.
• Glycoproteins and glycolipids are components
of cell membranes and receptors.
• Structural basis of many organisms.e.g. Cellulose in
plants, exoskeleton of insects, cell wall of microbes,
mucopolysaccharides and ground substance in
higher organisms.
Disaccharides
2 sugar units
Oligosacchari
des
3-9 units
Polysacchari
des
>10
e.g.Glucose,
fructose etc
e.g.Sucrose e.g.
Maltotriose
Homoglycans
e.g. starch,
glycogen
Heteroglycans
e.g. GAGs or
glycosaminoglycans
Monosaccharid
es
• Molecules having only one actual or potential sugar
group
No. of Generic
name carbon Aldoses Ketoses
3 Trioses
Aldotriose e.g. glyceraldehy
de
Ketotriose e.g. Dihydroxyaceto
ne
4 Tetroses
Aldotetrose e.g.
Erythrose
Ketotetrose e.g.
Erythrulose
5 Pentoses
Aldopentoses e.g
Arabinose, Xylose, Ribose
Ketopentoses e.g.
Xylulose, Ribulose
6 Hexoses
Aldohexose e.g. Gluc
ose, Galactose, Ma
nnose
Ketohexose e.g. Fructose
7 Heptoses
Aldoheptose: Glucoheptose Ketoheptose e.g Sedoheptulos
e
Hexoses of Physiologic
al Importance
Chemical Properties of Carbohydrates
Disaccharides
• When two monosaccharides are combined
together by glycosidic linkage, a disaccharide is
formed.
• Two types:-
Non-reducing
Sucrose
Trehalose
Cane
sugar in
yeast
Reducing
Lactose
Maltose
Milk
sugar
Malt
sugar
Sucrose
• Cane sugar, table sugar
• Glu + Fru (12)
• Sweetening agent
• Non-reducing
• No osazones
• Clinical Importance:-
-dental caries
-Bypasses metabolic check points- OBESITY
-“Sucrase deficiency “
Lactose
• Milk sugar
• Galactose + Glucose (β14)
• Reducing disaccharide
• Beta glycosidic linkage
• Osazone – Powder Puff or hedgehog
shaped
Maltose
• 2 glucose residues (1 4 linkage)
• Reducing disaccharide
• Malt sugar
• Osazone:- Star shaped or flower petal
shaped
Isomaltose
• 2 Glucose in  (16) linkage
• Reducing disaccharide
• Produced during partial hydrolysis of starch and
glycogen
Disaccharides of import
ance
Sug
ar
Compositi
on
Sourc
e
Clinical
Significance
Sucros
e
D-
glucopyranosyl-
(1-2) D-fructo
furanoside
Cane and beet
sugar, sorghum
and some fruits
and vegetables
Rare genetic lack of
sucrase leads to sucrose
intolerance— diarrhea and
flatulence
Lactos
e
D-
galactopyranosyl-
(1-4)D-
glucopyranose
Milk
Lack of lactase leads to
lactose intolerance diarrhea
and flatulence; may be
excreted in the urine in
pregnancy
Sug
ar
Compositi
on
Sourc
e
Clinical
Significance
Maltos
e
D-glucopyranosyl-
(1-4)-D-
glucopyranose
Enzymatic hydrolysis of
starch (amylase);
germinating cereals and
malt
Isomalto
se
D-glucopyranosyl-
(1-6)-D-
glucopyranose
Enzymatic hydrolysis of
starch (the branch points
in amylopectin)
Lactulo
se
D-
galactopyranosyl-
(1-4)-D-
fructofuranose
Heated milk (small
amounts),
mainly synthetic
Not hydrolyzed by
intestinal enzymes,
but fermented by
intestinal bacteria;
used as a mild
osmotic laxative
Trehalos
e
D-glucopyranosyl-
(1-1)-D-
glucopyranoside
Yeasts and fungi; the main
sugar of insect hemolymph
Homoglycan
Or
Homopolysaccharide
Heteroglycan
Or
Heteropolysaccharide
Homoglycans
• Starch
• Glycogen
• Cellulose
• Inulin
• Dextrans
• Chitin
Starch
• Carbohydrates of the plant kingdom
• Sources:
• Potatoes, tapioca, cereals (rice, wheat) and
other food grains
• Composed of Amylose &Amylopectin
• Amylose:
• When starch is treated with boiling water, 10 -20
% is solubilized.
• This part is called amylose, contains glucose
units with -1,4 glycosidic linkages.
• Mol wt =400,000 or more
• Amylopectin:
• The insoluble part absorbswater and forms
paste like gel;
• This is called as amylopectin.
• Amylopectin is also made up of glucose units,
but is highly branched with molecular weight
more than 1 million.
• The branching points are made by - 1, 6
linkage
Hydrolysis of starch
• Starch will form a blue coloured complex with iodine; this
color disappears on heating and reappears when cooled.
• This is a sensitive test for starch.
• When starch is hydrolyzed by mild acid, smaller and
smaller fragments are produced.
• The hydrolysis for a short time produces amylodextrin
(violet color with iodine and non-reducing).
• Further hydrolysis…………….
amylodex erythrodexarchrodextrinMaltose
Violet Red no color no color
Non reducing Non reducing Reducing Reducing
Action of amylases on starch
• Salivary amylases and pancreatic amylases are
 amylases, which act randomly on , 1-4
linkages to split starch into smaller units called
dextrins
• Beta amylases (plant origin – almonds etc) act
consecutively from one end.
• When beta amylases reach a branch point in
amylopectin, enzyme is blocked, leaving a large
molecule called as LIMIT DEXTRIN
Glycogen
• Storage form of energy in animal.
• Stored in liver and muscle
• Stores more glucose residues per gram than starch.
• More branched and compact than starch.
• Less osmotic pressure.
• More energy in a smaller space.
• Glycogen in liver (6-8%) is higher than that in the
muscles (1-2%).
• Liver glycogen - first line of defense against declining
blood glucose levels especially between meals.
• A homopolysaccharide: linear chain of (1→4) linked
glucosyl residues with branches joined by  (1→6)
linkages
Cellulose
• Glucose units combined by -1,4 linkages.
• Straight line str. with no branches.
• Mol wt 2-5 million.
• This bond is digested by cellobiases an enzyme not
present in humans.
• Herbivores animals have large caecum which harbor
bacteria which break cellulose.
• White ants (termites) and some wood fungi also have
cellulase.
• Commercial applications: nitrocellulose, cellulose
acetate membranes for electrophoresis ETC
Inulin
• D -fructose in -1,2 linkages.
• Source:
• Bulbs and tubers chicory, dahlia, dandelion,
onions, garlic.
• Not metabolized .
• Not absorbed nor secreted by kidneys.
• USE – to measure GFR.
Dextrans
• Highly branched homoglycan containing Glu
residues in 1-6, 1-4 and 1-3 linkages.
• Produced by microbes.
• Mol. wt:- 1-4 million.
• As large sized, they will not move out of vascular
compartment so used as plasma expanders.
Chitin
• N-acetyl glucosamine with beta 1,4 glycosidic
linkage
• Exoskeleton of crustacea and insects.
Heteroglycans
Mucopolysaccharides or GAG
[ URONIC ACID + AMINO SUGAR]n
Acetylated amino sugars, sulfate and carboxyl groups
may be present also
Heteropolysac
charides
• Polymers made from more than one kind of
monosaccharides or monosaccharide
derivatives.
Eg :
Glycosoaminoglycans, Agar
Agarose
• Long, Unbranched heteropolysaccharide, made
of repeating disaccharide units containing
uronic acid & amino sugars.
• Amino sugar – Glucosamine or Galactosamine
(Present in there acetylated form)
• Uronic acid – D-Glucuronic acid or L-Iduronic
acid
• GAGs are the most important group of
heteroglycan in humans.
• First isolated from mucin so
called mucopolysaccharides.
• Major components of extracellular matrix of
connective tissue, including bone and
cartilage, synovial fluid, vitreous humor
and secretions of mucus producing cells.
• Gel forming component of extracellular matrix
• The anionic groups (carboxy & sulfate groups) being
strongly hydrophilic tend to bind large amount of water
producing gel like matrix, that forms the bodies ground
substance.
• Heteropolysaccharide chains repel one another and
therefore
exist in extended conformation in solutions.
• This produces slippery consistency of mucus
secretions and synovial fluid.
• Structural support to connective tissue
• GAGs form matrix or ground substance that
stabilizes and supports the cellular and fibrous
components of tissues.
• Other functions:
• Playsan important role in mediating cell-cell
interactions
• Their slippery consistency makes them suitable
for a lubricant action in joints.
Classification
GAGS
Neutral
Acidic
Blood
group
substance
s
Sulfate
containing
Sulfate free
Hyaluronic
acid
Chondroitin
Sulphate
Dermatan
sulphate keratan
sulphate Heparin
80
Hyaluronic acid
• It is sulfate free GAG.
• Synovial fluid of joints, vitreous
humor, connective tissues and
cartilage.
Functions of Hyaluronic acid
• Serves as a lubricant and shock absorbant in
joints.
• Acts as seives in extracellular matrix.
• Permits cell migration during
morphogenesis & wound repair.
• Hyaluronidase is an enzyme that breaks
β1 – 4 linkages of hyaluronic acid.
• Presentin high concentration in seminal fluid,
& in certain snake and insect venoms.
• Hyaluronidase enzyme of semen degrades
the gel around ovum & allows effective
penetration of sperm into ovum, thus helps in
fertilization.
• The invasive power of some pathogenic
organism may be increased because they
secrete hyaluronidase.
Chondroitin 4-sulfate
• Most abundant GAG in
body.
• Widely distributed in bone, cartilage & tendons.
• Functions:
• In cartilage, it binds collagen & hold fibers in a
tight strong network.
• Role in Compressibility of cartilage in weight
bearing.
Dermatan sulfate
• Contains repeating units ofL-iduronic acid
and N- acetyl glucosamine 4 sulfate.
• Present in skin, cardiac valves & tendon.
• Function:
• Presentin sclera of eye where it has
important function in maintaining overall
shape of eye.
Heparin
• Only GAG present intracellular: In
granules of mast cells and also in lung,
liver and skin.
• Strongly acidic due to presence of more sulfate
group.
• Functions:
• It is an anticoagulant (prevents blood clotting)
• Heparin helps in the release of the enzyme
lipoprotein lipase (LPL) which helps to clear the
lipidemia after fatty meal – so called clearing
factor.
Heparan sulfate
• Structurally similar to heparin, but has a
• Lower molecular weight
• Contains higher acetyl groups & less sulf
ate group
• Predominant uronic acid is D-Glucuronic aci
d
• It is an extracellular GAG found in basement
membrane and is an essential component o
Keratan sulfate
• Only GAG with no uronic acid.
• Found in cornea & tendons.
• Function:
• Maintains the corneal
transparency.
Proteoglycan aggreg
ate
Blood group substances (blood gr Antigens)
• RBC membrane contains several antigenic
substance, based on which classified into
different blood groups.
• They contain carbohydrates as
glycoproteins or glycolipids.
• N-Acetylgalactosamine, galactose, fucose,
sialic acid etc are found in blood gr
substances.
• Carbohydrate content plays a determinant
role in blood grouping.
Agar
• Containsgalactose, glucose & other sugars.
• Obtained from sea weeds
• Functions:
• Cannot be digested by bacteria.
• So used as supporting agent to culture
bacterial colonies.
• Also as support medium of immuno
diffusion & immuno-electrophoresis.
Agarose
• Galactose and 3,6 anhydrous galactose
units
• Used as matrix for electrophoresis.
https://youtu.be/kIIS59cjzjI
Reference Books
• Test Book of Biochemistry- Harper
• Test Book of Biochemistry - Dr. U.Satyanarayana
• Test Book of Medical Biochemistry-DM.Vasudevan
• Test Book of Medical Biochemistry – MN Chatterjea
Thank you

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UNIT 1 Carbohydrate chemistry.pptx

  • 2. Carbohydrates • Carbohydrates are the most abundant organic molecules in nature. • Hydrates of carbon • Carbohydrates are defined as polyhydroxyaldehydes or ketones or compounds which produce them on hydrolysis. • Composed of carbon, hydrogen and oxygen
  • 3. • General molecular formula Cn (H2O)n • Some carbohydrates contain Sulphur, Nitrogen or Phosphorus • Exceptions are acetic acid C2H4O2 and lactic acid C3H6O3.
  • 4. Functions of Carbohydrates • Main sources of ENERGY in body (4kcal/g) – RBCs and Brain cells have an absolute requirement of carbohydrates. • Storage form of energy (starch and glycogen) • Excess carbohydrate is converted to fat. • Glycoproteins and glycolipids are components of cell membranes and receptors. • Structural basis of many organisms.e.g. Cellulose in plants, exoskeleton of insects, cell wall of microbes, mucopolysaccharides and ground substance in higher organisms.
  • 5. Disaccharides 2 sugar units Oligosacchari des 3-9 units Polysacchari des >10 e.g.Glucose, fructose etc e.g.Sucrose e.g. Maltotriose Homoglycans e.g. starch, glycogen Heteroglycans e.g. GAGs or glycosaminoglycans
  • 6. Monosaccharid es • Molecules having only one actual or potential sugar group No. of Generic name carbon Aldoses Ketoses 3 Trioses Aldotriose e.g. glyceraldehy de Ketotriose e.g. Dihydroxyaceto ne 4 Tetroses Aldotetrose e.g. Erythrose Ketotetrose e.g. Erythrulose 5 Pentoses Aldopentoses e.g Arabinose, Xylose, Ribose Ketopentoses e.g. Xylulose, Ribulose 6 Hexoses Aldohexose e.g. Gluc ose, Galactose, Ma nnose Ketohexose e.g. Fructose 7 Heptoses Aldoheptose: Glucoheptose Ketoheptose e.g Sedoheptulos e
  • 8. Chemical Properties of Carbohydrates
  • 9. Disaccharides • When two monosaccharides are combined together by glycosidic linkage, a disaccharide is formed. • Two types:- Non-reducing Sucrose Trehalose Cane sugar in yeast Reducing Lactose Maltose Milk sugar Malt sugar
  • 10. Sucrose • Cane sugar, table sugar • Glu + Fru (12) • Sweetening agent • Non-reducing • No osazones • Clinical Importance:- -dental caries -Bypasses metabolic check points- OBESITY -“Sucrase deficiency “
  • 11. Lactose • Milk sugar • Galactose + Glucose (β14) • Reducing disaccharide • Beta glycosidic linkage • Osazone – Powder Puff or hedgehog shaped
  • 12. Maltose • 2 glucose residues (1 4 linkage) • Reducing disaccharide • Malt sugar • Osazone:- Star shaped or flower petal shaped
  • 13. Isomaltose • 2 Glucose in  (16) linkage • Reducing disaccharide • Produced during partial hydrolysis of starch and glycogen
  • 14. Disaccharides of import ance Sug ar Compositi on Sourc e Clinical Significance Sucros e D- glucopyranosyl- (1-2) D-fructo furanoside Cane and beet sugar, sorghum and some fruits and vegetables Rare genetic lack of sucrase leads to sucrose intolerance— diarrhea and flatulence Lactos e D- galactopyranosyl- (1-4)D- glucopyranose Milk Lack of lactase leads to lactose intolerance diarrhea and flatulence; may be excreted in the urine in pregnancy
  • 15. Sug ar Compositi on Sourc e Clinical Significance Maltos e D-glucopyranosyl- (1-4)-D- glucopyranose Enzymatic hydrolysis of starch (amylase); germinating cereals and malt Isomalto se D-glucopyranosyl- (1-6)-D- glucopyranose Enzymatic hydrolysis of starch (the branch points in amylopectin) Lactulo se D- galactopyranosyl- (1-4)-D- fructofuranose Heated milk (small amounts), mainly synthetic Not hydrolyzed by intestinal enzymes, but fermented by intestinal bacteria; used as a mild osmotic laxative Trehalos e D-glucopyranosyl- (1-1)-D- glucopyranoside Yeasts and fungi; the main sugar of insect hemolymph
  • 17.
  • 18. Homoglycans • Starch • Glycogen • Cellulose • Inulin • Dextrans • Chitin
  • 19. Starch • Carbohydrates of the plant kingdom • Sources: • Potatoes, tapioca, cereals (rice, wheat) and other food grains • Composed of Amylose &Amylopectin • Amylose: • When starch is treated with boiling water, 10 -20 % is solubilized. • This part is called amylose, contains glucose units with -1,4 glycosidic linkages. • Mol wt =400,000 or more
  • 20. • Amylopectin: • The insoluble part absorbswater and forms paste like gel; • This is called as amylopectin. • Amylopectin is also made up of glucose units, but is highly branched with molecular weight more than 1 million. • The branching points are made by - 1, 6 linkage
  • 21.
  • 22. Hydrolysis of starch • Starch will form a blue coloured complex with iodine; this color disappears on heating and reappears when cooled. • This is a sensitive test for starch. • When starch is hydrolyzed by mild acid, smaller and smaller fragments are produced. • The hydrolysis for a short time produces amylodextrin (violet color with iodine and non-reducing). • Further hydrolysis……………. amylodex erythrodexarchrodextrinMaltose Violet Red no color no color Non reducing Non reducing Reducing Reducing
  • 23. Action of amylases on starch • Salivary amylases and pancreatic amylases are  amylases, which act randomly on , 1-4 linkages to split starch into smaller units called dextrins • Beta amylases (plant origin – almonds etc) act consecutively from one end. • When beta amylases reach a branch point in amylopectin, enzyme is blocked, leaving a large molecule called as LIMIT DEXTRIN
  • 24. Glycogen • Storage form of energy in animal. • Stored in liver and muscle • Stores more glucose residues per gram than starch. • More branched and compact than starch. • Less osmotic pressure. • More energy in a smaller space. • Glycogen in liver (6-8%) is higher than that in the muscles (1-2%). • Liver glycogen - first line of defense against declining blood glucose levels especially between meals.
  • 25. • A homopolysaccharide: linear chain of (1→4) linked glucosyl residues with branches joined by  (1→6) linkages
  • 26. Cellulose • Glucose units combined by -1,4 linkages. • Straight line str. with no branches. • Mol wt 2-5 million. • This bond is digested by cellobiases an enzyme not present in humans. • Herbivores animals have large caecum which harbor bacteria which break cellulose. • White ants (termites) and some wood fungi also have cellulase. • Commercial applications: nitrocellulose, cellulose acetate membranes for electrophoresis ETC
  • 27. Inulin • D -fructose in -1,2 linkages. • Source: • Bulbs and tubers chicory, dahlia, dandelion, onions, garlic. • Not metabolized . • Not absorbed nor secreted by kidneys. • USE – to measure GFR.
  • 28. Dextrans • Highly branched homoglycan containing Glu residues in 1-6, 1-4 and 1-3 linkages. • Produced by microbes. • Mol. wt:- 1-4 million. • As large sized, they will not move out of vascular compartment so used as plasma expanders.
  • 29. Chitin • N-acetyl glucosamine with beta 1,4 glycosidic linkage • Exoskeleton of crustacea and insects.
  • 31. Mucopolysaccharides or GAG [ URONIC ACID + AMINO SUGAR]n Acetylated amino sugars, sulfate and carboxyl groups may be present also
  • 32. Heteropolysac charides • Polymers made from more than one kind of monosaccharides or monosaccharide derivatives. Eg : Glycosoaminoglycans, Agar Agarose
  • 33. • Long, Unbranched heteropolysaccharide, made of repeating disaccharide units containing uronic acid & amino sugars. • Amino sugar – Glucosamine or Galactosamine (Present in there acetylated form) • Uronic acid – D-Glucuronic acid or L-Iduronic acid • GAGs are the most important group of heteroglycan in humans.
  • 34. • First isolated from mucin so called mucopolysaccharides. • Major components of extracellular matrix of connective tissue, including bone and cartilage, synovial fluid, vitreous humor and secretions of mucus producing cells.
  • 35. • Gel forming component of extracellular matrix • The anionic groups (carboxy & sulfate groups) being strongly hydrophilic tend to bind large amount of water producing gel like matrix, that forms the bodies ground substance. • Heteropolysaccharide chains repel one another and therefore exist in extended conformation in solutions. • This produces slippery consistency of mucus secretions and synovial fluid.
  • 36. • Structural support to connective tissue • GAGs form matrix or ground substance that stabilizes and supports the cellular and fibrous components of tissues. • Other functions: • Playsan important role in mediating cell-cell interactions • Their slippery consistency makes them suitable for a lubricant action in joints.
  • 38. Hyaluronic acid • It is sulfate free GAG. • Synovial fluid of joints, vitreous humor, connective tissues and cartilage.
  • 39. Functions of Hyaluronic acid • Serves as a lubricant and shock absorbant in joints. • Acts as seives in extracellular matrix. • Permits cell migration during morphogenesis & wound repair. • Hyaluronidase is an enzyme that breaks β1 – 4 linkages of hyaluronic acid. • Presentin high concentration in seminal fluid, & in certain snake and insect venoms.
  • 40. • Hyaluronidase enzyme of semen degrades the gel around ovum & allows effective penetration of sperm into ovum, thus helps in fertilization. • The invasive power of some pathogenic organism may be increased because they secrete hyaluronidase.
  • 41. Chondroitin 4-sulfate • Most abundant GAG in body.
  • 42. • Widely distributed in bone, cartilage & tendons. • Functions: • In cartilage, it binds collagen & hold fibers in a tight strong network. • Role in Compressibility of cartilage in weight bearing.
  • 43. Dermatan sulfate • Contains repeating units ofL-iduronic acid and N- acetyl glucosamine 4 sulfate.
  • 44. • Present in skin, cardiac valves & tendon. • Function: • Presentin sclera of eye where it has important function in maintaining overall shape of eye.
  • 45. Heparin • Only GAG present intracellular: In granules of mast cells and also in lung, liver and skin.
  • 46. • Strongly acidic due to presence of more sulfate group. • Functions: • It is an anticoagulant (prevents blood clotting) • Heparin helps in the release of the enzyme lipoprotein lipase (LPL) which helps to clear the lipidemia after fatty meal – so called clearing factor.
  • 47. Heparan sulfate • Structurally similar to heparin, but has a • Lower molecular weight • Contains higher acetyl groups & less sulf ate group • Predominant uronic acid is D-Glucuronic aci d • It is an extracellular GAG found in basement membrane and is an essential component o
  • 48. Keratan sulfate • Only GAG with no uronic acid. • Found in cornea & tendons. • Function: • Maintains the corneal transparency.
  • 50. Blood group substances (blood gr Antigens) • RBC membrane contains several antigenic substance, based on which classified into different blood groups. • They contain carbohydrates as glycoproteins or glycolipids. • N-Acetylgalactosamine, galactose, fucose, sialic acid etc are found in blood gr substances. • Carbohydrate content plays a determinant role in blood grouping.
  • 51. Agar • Containsgalactose, glucose & other sugars. • Obtained from sea weeds • Functions: • Cannot be digested by bacteria. • So used as supporting agent to culture bacterial colonies. • Also as support medium of immuno diffusion & immuno-electrophoresis.
  • 52. Agarose • Galactose and 3,6 anhydrous galactose units • Used as matrix for electrophoresis.
  • 53.
  • 55. Reference Books • Test Book of Biochemistry- Harper • Test Book of Biochemistry - Dr. U.Satyanarayana • Test Book of Medical Biochemistry-DM.Vasudevan • Test Book of Medical Biochemistry – MN Chatterjea