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Carbohydrates
Carbohydrates
• Carbohydrate literary means hydrated carbon. Carbohydrates are
composed of carbon, hydrogen and oxygen and the ratio of hydrogen
and oxygen is the same as in water.
• Carbohydrates polyhydroxy aldehydes or ketones or complex
substances that on hydrolysis yield polyhdroxy aldehydes or ketones
subunits.
Carbohybrates or Saccharides (Sugars)
Poly hydroxy (OH) ketones orAldehydes
Hydrates of Carb on: Cm (H2O)n
C(H2O): formaldehyde
C2(H2O)2: ddiose: glycolaldehyde
C3(H2O)3: Triose
C4(H2O)4: Tetrose
C5(H2O)5: Pentose
C6(H2O)6: Hexose
• Aldose: Glucose Ketose: Fructose
Exceptions
• General formula: Cm (H2O)n
• Carbohydrates with different formula
• Uronic acids: C6H9O7
• Fucose: C6H12O5
• Noncarbohydrates with formula of carbohydrates
• Formaldehyde: CH2O
• Inositol: C6(H2O)6
Examples of Carbohydrates
• Glucose: major metabolic fuel of mammals
• Glycogen: storage; in animals
• Starch: Storage; in plants
• Cellulose: structure; in plants; in paper
• Chitin: stucture; in Arthropods
• Ribose: RNA, ATP, NAD
• Deoxyribose: DNA
• lactose: Milk
Foods high in carbohydrates
• Sweets
• Soft drinks
• Breads
• Beans, peas
• Cereals, Rice, maize, barley, wheat, corn
• apricot, dates, blueberry, banana, fig, grapes, apple, orange, pear,
pineapple, strawberry, watermelon and raisins
• macaroni, spaghetti, potato, carrot
Classification
Class Test
• Define matter, mass, chemistry, nursing.
• Define Bohr’s and Rutherford’s model of atom.
• Define types of chemical reactions.
• Define acids and bases.
• Draw structure for: 4, 5-diethyl-5-methylocta-3-ene-1-yne
• Write IUPAC name for:
Monosaccharides (simplest, colorless, water
soluble, sweet, crystaline solids)
• They can be classified according to three different ways
• 1. Placement of C=O group (Aldo, Keto)
• 2. The number of Carbon atoms (tri, tetra, penta)
• 3. Chiral Carbon handedness (D, L)
• 4. rotation of plane polarized light (d, l)
Placement of CO group
• 1. Aldoses: Aldehyde group
• 2. Ketoses: Ketone group
Number of carbon atoms
• Trioses
• Tetroses
• Pentoses
• Hexoses
• Heptoses
• Octoses
• Nonoses
Aldoses (ose)
Aldotriose: Triose
Aldotetrose:Tetroses
Alodpentose: Pentoses
Aldohexose: Hexoses
Ketoses (ulose)
Ketotriose: Triulose
Ketotetrose: Tetrulose
Ketopentose: Pentulose
Keto Hexose: Hexulose
• Water + CO2 Carbohybrates (Plants) Animals
Mono and di ends in (ose)
• Mono and di also called sugars
• Blood sugar: glucose
• Table sugar: sucrose= Glucose+fructose
• Milk sugar: lactose=Galactose+glucose
• Maltose: Glucose+glucose
Isomerism
• In chemistry, isomers (isos = "equal", méros = "part") are compounds
with the same molecular formula but different structural formulas.
• Structural Isomerism
• Stereoisomerism
Chain isomers
Position isomers
Functional isomers
Metamers
Tautomers
Ring chain isomers
Anomers
Geometric isomers
Stereoisomerism
Stereoisomerism
• Same structural formula
• but differ in spatial configuration
• With respect to the Penultimate Carbon atom
• glucose has 2 stereoisomers D-glucose and
• L-glucose
Chiral carbon
Optical activity (d, l)
Enantiomers
• Mirror images, non superimposible
Diastereomers
• Non mirror images and non superimposible
Epimers
• Change in conformation around only one carbon
Fischer projection
Fischer projection
• The Fischer projection is a two-dimensional representation of a three-
dimensional organic molecule by projection.
• All bonds: horizontal or vertical lines.
• carbon chain: vertical (carbon atoms in center)
• C1: top.
• In an aldose, carbon of the aldehyde: C1
• ketose the carbon of the ketone: lowest number
• horizontal bonds: toward the viewer
• vertical bonds away from the viewer.
Haworth projections
A Haworth projection is a common way of representing the cyclic structure of
monosaccharides with a simple three-dimensional perspective.
A Haworth projection has the following characteristics
• atoms numbered 1 to 6: carbon atoms.
• Carbon 1: Anomeric Carbon.
• atoms 1 to 6 have extra hydrogen atoms not depicted.
• A thicker line: closer to the observer. 2 and 3 ( OH)
• atoms 1 and 4: farther from the observer.
• 5: farthest.
• groups below the plane of the ring: equivalent to right-hand side of a
Fischer projection.
Cyclic isomers
H O
OH
H
OHH
OH
CH2OH
H
OH
H H O
OH
H
OHH
OH
CH2OH
H
H
OH
-D-glucose -D-glucose
23
4
5
6
1 1
6
5
4
3 2
H
CHO
C OH
C HHO
C OHH
C OHH
CH2OH
1
5
2
3
4
6
D-glucose
(linear form)
Anomers
Alpha Beta
Reducing sugars
• Having an aldehyde group in open chain form
• Mono: Glucose, fructose, glyceraldehyde, galactose
• Di: Lactose, Maltose
• Di: Non reducing: Sucrose, trehalose
Functions
• Providing energy and regulation of blood glucose
• Sparing the use of proteins for energy
• Prevent breakdown of fatty acids
• Biological recognition processes
• Flavor and Sweeteners
• Dietary fiber which helps prevent constipation
• Carbohydrate is necessary for the regulation of nerve tissue and is
the source of energy for the brain.
• Polysaccharides: storage of energy (e.g., starch and glycogen),
• structural components (e.g., cellulose in plants and chitin in
arthropods).
• ribose in coenzymes (e.g., ATP, FAD, and NAD) and the backbone
of RNA.
• Deoxyribose: component of DNA.
• Heparin is used to treat and prevent blood clots from forming,
especially in the lungs and legs.
Chemical Properties
• Osazone formation with phenlyhydrazine
• Oxidation to carboxylic acid.
• oxidation of an aldehyde (aldose) to an aldonic acid,
• oxidation of the alcohol on the highest-numbered carbon atom to a uronic acid.
• Reduction to Alcohols
• Many aldoses, because of the aldehyde group, are reducing sugars. A number of tests for
reducing sugars, include using Fehling’s solution or Benedict’s solution. These tests are
useful to check for glucose in the urine of a diabetics
• Monosaccharides, like all alcohols, may react with acids to form esters.
• Any of the alcohol groups may react to a phosphoric acid (phosphate sugar)
• D-ribose-1-phosphate.
• The joining of two or more monosaccharides forms an oligosaccharide or a polysaccharide.
• Cyanohydrin reaction
• Lobry-de Bruyn-van Ekenstein transformation
• Amadori rearrangement
• Wohl degradation
• Osazone formation with phenlyhydrazine
Oxidation 1: aldonic acid formation
Oxidation 2: uronic acid formation
Reduction
Benedict’s test
Ester formation
Alcohol + Phosphate group
Self Study
Cyanohydrin reaction
Lobry-de Bruyn-van Ekenstein transformation
• Base or acid catalyzed transformation of an aldose into the ketose
isomer or vice versa,
Amadori rearrangement
Wohl degredation
Other Reactions
Glycosidic bond formation
Disaccharides (Examples)
H O
OH
H
OHH
OH
CH2OH
H
O H
OH
H
OHH
OH
CH2OH
H
O
HH
1
23
5
4
6
1
23
4
5
6
maltose
sucrose
Polysaccharides
H O
OH
H
OHH
OH
CH2OH
H
O H
H
OHH
OH
CH2OH
H
O
HH H O
O
H
OHH
OH
CH2OH
H
H H O
H
OHH
OH
CH2OH
H
OH
HH O
O
H
OHH
OH
CH2OH
H
O
H
1
6
5
4
3
1
2
amylose
cellulose
H O
OH
H
OHH
OH
CH2OH
H
O
H
OHH
OH
CH2OH
H
O
H H O
O H
OHH
OH
CH2OH
H
H O
H
OHH
OH
CH2OH
H
H
OHH O
O H
OHH
OH
CH2OH
H
O
H H H H
1
6
5
4
3
1
2
H O
OH
H
OHH
OH
CH2OH
H
O H
H
OHH
OH
CH2OH
H
O
HH H O
O
H
OHH
OH
CH2
H
H H O
H
OHH
OH
CH2OH
H
OH
HH O
O
H
OHH
OH
CH2OH
H
O
H
O
1 4
6
H O
H
OHH
OH
CH2OH
H
H H O
H
OHH
OH
CH2OH
H
H
O
1
OH
3
4
5
2
amylopectin
Glycogen is similar to amylopectin except more branching
Diseases (Assignment)
• Diabetes mellitus
• Galactosemia
• Glycogen storage disease
• Lactose intolerance
• Dental carries
• Hypoglycemia

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Carbohydrates

  • 2. Carbohydrates • Carbohydrate literary means hydrated carbon. Carbohydrates are composed of carbon, hydrogen and oxygen and the ratio of hydrogen and oxygen is the same as in water. • Carbohydrates polyhydroxy aldehydes or ketones or complex substances that on hydrolysis yield polyhdroxy aldehydes or ketones subunits.
  • 3. Carbohybrates or Saccharides (Sugars) Poly hydroxy (OH) ketones orAldehydes Hydrates of Carb on: Cm (H2O)n C(H2O): formaldehyde C2(H2O)2: ddiose: glycolaldehyde C3(H2O)3: Triose C4(H2O)4: Tetrose C5(H2O)5: Pentose C6(H2O)6: Hexose • Aldose: Glucose Ketose: Fructose
  • 4. Exceptions • General formula: Cm (H2O)n • Carbohydrates with different formula • Uronic acids: C6H9O7 • Fucose: C6H12O5 • Noncarbohydrates with formula of carbohydrates • Formaldehyde: CH2O • Inositol: C6(H2O)6
  • 5. Examples of Carbohydrates • Glucose: major metabolic fuel of mammals • Glycogen: storage; in animals • Starch: Storage; in plants • Cellulose: structure; in plants; in paper • Chitin: stucture; in Arthropods • Ribose: RNA, ATP, NAD • Deoxyribose: DNA • lactose: Milk
  • 6. Foods high in carbohydrates • Sweets • Soft drinks • Breads • Beans, peas • Cereals, Rice, maize, barley, wheat, corn • apricot, dates, blueberry, banana, fig, grapes, apple, orange, pear, pineapple, strawberry, watermelon and raisins • macaroni, spaghetti, potato, carrot
  • 7.
  • 9. Class Test • Define matter, mass, chemistry, nursing. • Define Bohr’s and Rutherford’s model of atom. • Define types of chemical reactions. • Define acids and bases. • Draw structure for: 4, 5-diethyl-5-methylocta-3-ene-1-yne • Write IUPAC name for:
  • 10. Monosaccharides (simplest, colorless, water soluble, sweet, crystaline solids) • They can be classified according to three different ways • 1. Placement of C=O group (Aldo, Keto) • 2. The number of Carbon atoms (tri, tetra, penta) • 3. Chiral Carbon handedness (D, L) • 4. rotation of plane polarized light (d, l)
  • 11. Placement of CO group • 1. Aldoses: Aldehyde group • 2. Ketoses: Ketone group
  • 12. Number of carbon atoms • Trioses • Tetroses • Pentoses • Hexoses • Heptoses • Octoses • Nonoses
  • 14. Ketoses (ulose) Ketotriose: Triulose Ketotetrose: Tetrulose Ketopentose: Pentulose Keto Hexose: Hexulose
  • 15. • Water + CO2 Carbohybrates (Plants) Animals
  • 16. Mono and di ends in (ose) • Mono and di also called sugars • Blood sugar: glucose • Table sugar: sucrose= Glucose+fructose • Milk sugar: lactose=Galactose+glucose • Maltose: Glucose+glucose
  • 17. Isomerism • In chemistry, isomers (isos = "equal", méros = "part") are compounds with the same molecular formula but different structural formulas. • Structural Isomerism • Stereoisomerism
  • 18.
  • 19.
  • 20.
  • 21.
  • 22.
  • 32. Stereoisomerism • Same structural formula • but differ in spatial configuration • With respect to the Penultimate Carbon atom • glucose has 2 stereoisomers D-glucose and • L-glucose
  • 35.
  • 36.
  • 37. Enantiomers • Mirror images, non superimposible
  • 38.
  • 39.
  • 40. Diastereomers • Non mirror images and non superimposible
  • 41.
  • 42. Epimers • Change in conformation around only one carbon
  • 44. Fischer projection • The Fischer projection is a two-dimensional representation of a three- dimensional organic molecule by projection.
  • 45. • All bonds: horizontal or vertical lines. • carbon chain: vertical (carbon atoms in center) • C1: top. • In an aldose, carbon of the aldehyde: C1 • ketose the carbon of the ketone: lowest number • horizontal bonds: toward the viewer • vertical bonds away from the viewer.
  • 46. Haworth projections A Haworth projection is a common way of representing the cyclic structure of monosaccharides with a simple three-dimensional perspective.
  • 47. A Haworth projection has the following characteristics • atoms numbered 1 to 6: carbon atoms. • Carbon 1: Anomeric Carbon. • atoms 1 to 6 have extra hydrogen atoms not depicted. • A thicker line: closer to the observer. 2 and 3 ( OH) • atoms 1 and 4: farther from the observer. • 5: farthest. • groups below the plane of the ring: equivalent to right-hand side of a Fischer projection.
  • 48. Cyclic isomers H O OH H OHH OH CH2OH H OH H H O OH H OHH OH CH2OH H H OH -D-glucose -D-glucose 23 4 5 6 1 1 6 5 4 3 2 H CHO C OH C HHO C OHH C OHH CH2OH 1 5 2 3 4 6 D-glucose (linear form)
  • 50. Reducing sugars • Having an aldehyde group in open chain form • Mono: Glucose, fructose, glyceraldehyde, galactose • Di: Lactose, Maltose • Di: Non reducing: Sucrose, trehalose
  • 51.
  • 52. Functions • Providing energy and regulation of blood glucose • Sparing the use of proteins for energy • Prevent breakdown of fatty acids • Biological recognition processes • Flavor and Sweeteners • Dietary fiber which helps prevent constipation • Carbohydrate is necessary for the regulation of nerve tissue and is the source of energy for the brain. • Polysaccharides: storage of energy (e.g., starch and glycogen), • structural components (e.g., cellulose in plants and chitin in arthropods). • ribose in coenzymes (e.g., ATP, FAD, and NAD) and the backbone of RNA. • Deoxyribose: component of DNA. • Heparin is used to treat and prevent blood clots from forming, especially in the lungs and legs.
  • 53. Chemical Properties • Osazone formation with phenlyhydrazine • Oxidation to carboxylic acid. • oxidation of an aldehyde (aldose) to an aldonic acid, • oxidation of the alcohol on the highest-numbered carbon atom to a uronic acid. • Reduction to Alcohols • Many aldoses, because of the aldehyde group, are reducing sugars. A number of tests for reducing sugars, include using Fehling’s solution or Benedict’s solution. These tests are useful to check for glucose in the urine of a diabetics • Monosaccharides, like all alcohols, may react with acids to form esters. • Any of the alcohol groups may react to a phosphoric acid (phosphate sugar) • D-ribose-1-phosphate. • The joining of two or more monosaccharides forms an oligosaccharide or a polysaccharide. • Cyanohydrin reaction • Lobry-de Bruyn-van Ekenstein transformation • Amadori rearrangement • Wohl degradation
  • 54. • Osazone formation with phenlyhydrazine
  • 55. Oxidation 1: aldonic acid formation
  • 56. Oxidation 2: uronic acid formation
  • 63. Lobry-de Bruyn-van Ekenstein transformation • Base or acid catalyzed transformation of an aldose into the ketose isomer or vice versa,
  • 68. Disaccharides (Examples) H O OH H OHH OH CH2OH H O H OH H OHH OH CH2OH H O HH 1 23 5 4 6 1 23 4 5 6 maltose sucrose
  • 69. Polysaccharides H O OH H OHH OH CH2OH H O H H OHH OH CH2OH H O HH H O O H OHH OH CH2OH H H H O H OHH OH CH2OH H OH HH O O H OHH OH CH2OH H O H 1 6 5 4 3 1 2 amylose cellulose H O OH H OHH OH CH2OH H O H OHH OH CH2OH H O H H O O H OHH OH CH2OH H H O H OHH OH CH2OH H H OHH O O H OHH OH CH2OH H O H H H H 1 6 5 4 3 1 2
  • 70. H O OH H OHH OH CH2OH H O H H OHH OH CH2OH H O HH H O O H OHH OH CH2 H H H O H OHH OH CH2OH H OH HH O O H OHH OH CH2OH H O H O 1 4 6 H O H OHH OH CH2OH H H H O H OHH OH CH2OH H H O 1 OH 3 4 5 2 amylopectin Glycogen is similar to amylopectin except more branching
  • 71.
  • 72. Diseases (Assignment) • Diabetes mellitus • Galactosemia • Glycogen storage disease • Lactose intolerance • Dental carries • Hypoglycemia