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CARBOHYDRATES
• Aldehyde or Ketone derivatives of polyhydroxy
alcohols.
General formula
(CH2O)n
BIO MEDICAL IMPORTANCE
• Most abundant bio molecules.
• Main source of energy (4 kcal/gm) .
• Absolutely required for RBCs...
CLASSIFICATION
• Monosaccharides
• Disaccharides
• Oligosaccharides
• Polysaccharides
• Derived carbohydrates
MONOSACCHARIDES
• Simplest sugars, cant be hydrolyzed into simpler
molecules.
• Further classified as,
Aldoses
Ketoses
NAME GENERAL
FORMULA
ALDOSES KETOSES
TRIOSES C3H6O3 GLYCER-
- ALDEHYDE
DIHYDROXY-
-ACETONE
TETROSES C4H8O4 ERYTHROSE ERYTH...
DISACCHARIDES
• Condensation products of 2 monosaccharide units.
MALTOSE (D Glucose + D Glucose)
SUCROSE (D Glucose + D Fr...
OLIGO SACCHARIDES
• Condensation products of 3-10 mono saccharide units,most
of them are not digested by human enzymes.
α ...
POLY SACCHARIDES
• Condensation products of > 10 mono saccharide
units.
HOMO POLY SACCHARIDES
HETRO POLY SACCHARIDES
HOMO POLYSACCHARIDES
• Have only one type of mono saccharide units.
• STARCH GLYCOGEN
• CELLULOSE INULIN
• DEXTRIN DEXTRAN...
HETRO POLYSACCHARIDES
MUCO POLY SACCHARIDES
• Also known as Glycosaminoglycan.
• Hyaluronic Acid,Chondriotin sulfate, Hepa...
DERIVED CARBOHYDRATES.
• Reduction products i.e. Polyols (glycerol)
• Oxidation products i.e. sugar acids
• Deoxy sugars i...
MONOSACCHARIDES
TRIOSES
• Glyceraldehyde & Dihydroxy acetone.
1 Intermediates of glycolysis.
2 Precursor of Glycerol
TETRO...
DEOXY SUGARS
• L- Fucose
• Deoxy Glucose
• D- Ribose
• L- Arabinose
• D- xylose
HEXOSES
• Glucose
• Fructose
• Galactose
• Mannose
MONOSACCHARIDES
PHYSICAL PROPERTIES
• Colorless, crystalline solids , sweet taste, water
soluble compounds.
• Aldoses
• Ketoses
• Poly Hyd...
• Dihydroxy acetone (ketotriose) is an exception,
(does not have any asymmetric carbon).
• Glyceraldehyde (aldotriose) is ...
STRUCTURAL ASPECTS
• ISOMERISM IN MONOSACCHARIDES
1. Stereo isomerism
2. Enantiomers
3. D & L isomers
4. Optical isomers
5...
STEROISOMERISM
• 2 or more Monosaccharides having same formula, but
differing from each other in structural configuration ...
ASYMMETRICAL(CHIRAL) CARBON
• 4 different groups attached to the same carbon .
• Parent compound (reference molecule) is
•...
• In general a molecule with n chiral center can have 2n stereo
isomers.
• Glyceraldehyde 21
• Glucose 2 4
ENANTIOMERS
These are mirror images of
each other.
They form D & L isomers.
All mono saccharides can
be considered to be
d...
• The configuration of H & OH groups at the second Carbon
atom of Glyceraldehyde forms D & L sugars.
• Penultimate carbon ...
• Non super imposable complete mirror images, differ
in configuration at every chiral center.
• In D form OH group is on t...
OPTICAL ISOMERISM
• Presence of asymmetric C atom confers optical
activity to the carbohydrates.
• When a beam of plane po...
OPTICAL ISOMERISM
• The direction of rotation of plane polarized light is
independent of the stereo-chemistry of sugar.
• ...
• Plane polarized light does not rotate to right or left, if
• Compound does not possess plane of asymmetry.
• Equal amoun...
EPIMERS
• Sugars that differ only in the configuration
around one Carbon atom (other than
reference carbon).
ALDOSE-KETOSE ISOMERS
CYCLIC STUCTURE OF MONO
SACCHARIDES
• Cyclic structures are formed by the reaction between
an ALDEHYDE/KETONE group and a HYDROXYL group
in a monosaccharide w...
• The open chain form (FISCHER PROJECTION) is found in <
0.1% of the molecules in an aqueous solution.
• An intra molecula...
HEMI ACETAL LINKAGE
HEMIKETAL LINKAGE
HEMI KETAL LINKAGE
• Condensation between Ketone group and a OH group forms
the hemi Ketal linkage.
• Condensation between...
• OH group at C-5 / C-6 reacts with the Keto group at C-
2, forming a FURANOSE/PYRANOSE cyclic structure
having a hemi Ket...
• In Aldohexoses the OH group at C-5 reacts with the c=o
group and forms a six member
• ring---PYRAN RING .
• Sugars havin...
ANOMERS
• Anomeric carbon by giving an additional chiral carbon
makes the total isomers 25. (32)
• Anomeric carbon gives 2...
MUTA ROTATION
• In Glucose solution ,2/3 of sugar exist as β form,&
1/3 as α form.
• Inter conversion of α & β forms is ca...
• When plane polarized light is passed through a Molar
solution of D- Glucose, Its specific rotation keeps on
changing
• α...
CLINICAL SIGNIFICANCE
• α
& β Anomers can be obtained in pure forms.
•
• It is possible to determine the sugar content of
...
PYRANOSE/FURANOSE ISOMERS
BOAT & CHAIR ISOMERS
Visit us
• https://iaanatorg.wixsite.com/welfare
• Send us feedback
• mailto:iaanat.org@gmail.com
• Our page on facebook
•...
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
Chemistry of carbohydrates and isomerism
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Chemistry of carbohydrates and isomerism

carbohydrates with their brief introduction and their classification. then structural features of carbohydrates

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Chemistry of carbohydrates and isomerism

  1. 1. CARBOHYDRATES • Aldehyde or Ketone derivatives of polyhydroxy alcohols. General formula (CH2O)n
  2. 2. BIO MEDICAL IMPORTANCE • Most abundant bio molecules. • Main source of energy (4 kcal/gm) . • Absolutely required for RBCs’ & brain cells. • Storage form of energy i.e. starch & glycogen. • Required for oxidation of fats. • Excess CHO are converted into fats. • Glyco protein & Glyco lipids are components of cell membrane. • Structural basis of many organisms. • Used as drugs i.e. antibiotics & cardiac Glycosides.
  3. 3. CLASSIFICATION • Monosaccharides • Disaccharides • Oligosaccharides • Polysaccharides • Derived carbohydrates
  4. 4. MONOSACCHARIDES • Simplest sugars, cant be hydrolyzed into simpler molecules. • Further classified as, Aldoses Ketoses
  5. 5. NAME GENERAL FORMULA ALDOSES KETOSES TRIOSES C3H6O3 GLYCER- - ALDEHYDE DIHYDROXY- -ACETONE TETROSES C4H8O4 ERYTHROSE ERYTHROLUSE PENTOSES C5H10O5 RIBOSE RIBULOSE HEXOSES C6H12O6 GLUCOSE FRUCTOSE HEPTOSES C7H14O7 SEDOHEPTOLUSE NONOSES C9H18O9 NEURAMINIC- -ACID
  6. 6. DISACCHARIDES • Condensation products of 2 monosaccharide units. MALTOSE (D Glucose + D Glucose) SUCROSE (D Glucose + D Fructose) LACTOSE (D Glucose + D Galactose)
  7. 7. OLIGO SACCHARIDES • Condensation products of 3-10 mono saccharide units,most of them are not digested by human enzymes. α DEXTRINS MALTO TRIOSE
  8. 8. POLY SACCHARIDES • Condensation products of > 10 mono saccharide units. HOMO POLY SACCHARIDES HETRO POLY SACCHARIDES
  9. 9. HOMO POLYSACCHARIDES • Have only one type of mono saccharide units. • STARCH GLYCOGEN • CELLULOSE INULIN • DEXTRIN DEXTRAN • CHITIN
  10. 10. HETRO POLYSACCHARIDES MUCO POLY SACCHARIDES • Also known as Glycosaminoglycan. • Hyaluronic Acid,Chondriotin sulfate, Heparin sulfate, Keratin sulfate, Dermatin sulfate, Blood group substances. GLYCO CONGUGATES • Proteo glycans • Glyco lipids • Glyco proteins
  11. 11. DERIVED CARBOHYDRATES. • Reduction products i.e. Polyols (glycerol) • Oxidation products i.e. sugar acids • Deoxy sugars i.e. DNA
  12. 12. MONOSACCHARIDES TRIOSES • Glyceraldehyde & Dihydroxy acetone. 1 Intermediates of glycolysis. 2 Precursor of Glycerol TETROSES • Erythrose-4-PO4 1 Intermediate of HMP shunt.
  13. 13. DEOXY SUGARS • L- Fucose • Deoxy Glucose • D- Ribose • L- Arabinose • D- xylose
  14. 14. HEXOSES • Glucose • Fructose • Galactose • Mannose
  15. 15. MONOSACCHARIDES
  16. 16. PHYSICAL PROPERTIES • Colorless, crystalline solids , sweet taste, water soluble compounds. • Aldoses • Ketoses • Poly Hydroxy alcohols i.e. having (OH-) groups • Depending upon the no. of (OH-) groups, they contain one or more centre of Asymmetry, which affects their optical & biological activity.
  17. 17. • Dihydroxy acetone (ketotriose) is an exception, (does not have any asymmetric carbon). • Glyceraldehyde (aldotriose) is called as the “REFERENCE SUGAR”. Carbonyl carbon Asymmetric carbon
  18. 18. STRUCTURAL ASPECTS • ISOMERISM IN MONOSACCHARIDES 1. Stereo isomerism 2. Enantiomers 3. D & L isomers 4. Optical isomers 5. Aldose-Ketose isomers 6. Anomers 7. Epimers 8. Pyranose & Furanose isomers
  19. 19. STEROISOMERISM • 2 or more Monosaccharides having same formula, but differing from each other in structural configuration i.e. spatial arrangement of H or OH atoms in their structure.
  20. 20. ASYMMETRICAL(CHIRAL) CARBON • 4 different groups attached to the same carbon . • Parent compound (reference molecule) is • Glyceraldehyde (1 asymmetric C).
  21. 21. • In general a molecule with n chiral center can have 2n stereo isomers. • Glyceraldehyde 21 • Glucose 2 4
  22. 22. ENANTIOMERS These are mirror images of each other. They form D & L isomers. All mono saccharides can be considered to be derived from Glyceraldehyde.
  23. 23. • The configuration of H & OH groups at the second Carbon atom of Glyceraldehyde forms D & L sugars. • Penultimate carbon atom is the reference carbon for naming D & L mirror images.
  24. 24. • Non super imposable complete mirror images, differ in configuration at every chiral center. • In D form OH group is on the RIGHT , while in L form OH group is on the LEFT of the chiral carbon. • D & L isomers differ from each other by orientation around PENULTIMATE CARBON (C -5 in case of Glucose molecule) ,farthest from the carbonyl(C= O)carbon. • Human body can metabolize D-sugars only. • Naturally occuring sugars are D-sugars except L-Arabinose .
  25. 25. OPTICAL ISOMERISM • Presence of asymmetric C atom confers optical activity to the carbohydrates. • When a beam of plane polarized light is passed through a carbohydrate solution • It will rotate the light either • to right DEXTRO ROTATORY(+) • to left LEVO ROTATORY (-)
  26. 26. OPTICAL ISOMERISM • The direction of rotation of plane polarized light is independent of the stereo-chemistry of sugar. • Sugar may be designated as, D(-) ,D(+) or L(-) ,L(+) • Naturally occuring form of Fructose is D but it is levo rotatory. i.e. ( D-) • Glucose is D sugar, but dextro rotatory i.e. (D+)
  27. 27. • Plane polarized light does not rotate to right or left, if • Compound does not possess plane of asymmetry. • Equal amounts of dextro or levo isomers are present RECEMIC MIXTURE. • Meso compounds having asymmetric carbon but due to internal compensation i.e. Meso tartaric acid.
  28. 28. EPIMERS • Sugars that differ only in the configuration around one Carbon atom (other than reference carbon).
  29. 29. ALDOSE-KETOSE ISOMERS
  30. 30. CYCLIC STUCTURE OF MONO SACCHARIDES
  31. 31. • Cyclic structures are formed by the reaction between an ALDEHYDE/KETONE group and a HYDROXYL group in a monosaccharide with 5 or more carbon atoms. • Cyclic structure is thermodynamically favored and accounts for many properties of mono - saccharides
  32. 32. • The open chain form (FISCHER PROJECTION) is found in < 0.1% of the molecules in an aqueous solution. • An intra molecular reaction in which one of the OH group of the sugar is added to the Aldehyde/ Ketone group of the same molecule ---- forms a cyclic structure. • The cyclic (ring) structure is called ----------- HAWORTH PROJECTION. • The carbonyl carbon(C-1 of Aldose /C-2 OF KETOSE) in ring structure is called ANOMERIC CARBON
  33. 33. HEMI ACETAL LINKAGE
  34. 34. HEMIKETAL LINKAGE
  35. 35. HEMI KETAL LINKAGE • Condensation between Ketone group and a OH group forms the hemi Ketal linkage. • Condensation between the Aldehyde/Keto group is in 1:1. • As a result of these linkages ANOMERIC CARBON gives an additional asymmetric carbon. • Depending upon the configuration, OH group are found above or below the ring. • OH group on the right in Fischer projection appear under the ring in Haworth projection ,while those on the left are above the ring.
  36. 36. • OH group at C-5 / C-6 reacts with the Keto group at C- 2, forming a FURANOSE/PYRANOSE cyclic structure having a hemi Ketal linkage. • D-Fructose readily forms the Furanose ring. • Common anomer of Fructose is the β - D Fructose.
  37. 37. • In Aldohexoses the OH group at C-5 reacts with the c=o group and forms a six member • ring---PYRAN RING . • Sugars having this ring are called PYRANOSES. • If the OH group at C-4 reacts, a five member ring--- FURAN RING is formed & • Sugars are called FURANOSES. • OH group to the right is below the plane----α • Oh group to the left is above the plane of symmetry---β
  38. 38. ANOMERS • Anomeric carbon by giving an additional chiral carbon makes the total isomers 25. (32) • Anomeric carbon gives 2 stereo isomers i.e. α & β ANOMERS . • α & β forms are not Enantiomers. • They differ only in respect to configuration around Anomeric carbon. • They are present only in cyclic form, & do not show the Aldehyde group normally present in Glucose. • Ring structure is also called AMYLENE OXIDE . •
  39. 39. MUTA ROTATION • In Glucose solution ,2/3 of sugar exist as β form,& 1/3 as α form. • Inter conversion of α & β forms is called MUTA ROTATION . • In the solution there is opening of Hemiacetal ring to form traces of Aldehyde sugar & then Re condensation to the cyclic form.
  40. 40. • When plane polarized light is passed through a Molar solution of D- Glucose, Its specific rotation keeps on changing • α- D Glucose in the solution shows --+112˳ while β- Glucose shows ---- +19˳. After a certain period of time two forms reach at an end point---- +19˳. Mutarotation leads to an equilibrium between α & β forms in which 62% of the molecules are present in the β form , while 38% in the α form. a
  41. 41. CLINICAL SIGNIFICANCE • α & β Anomers can be obtained in pure forms. • • It is possible to determine the sugar content of different beverages.
  42. 42. PYRANOSE/FURANOSE ISOMERS
  43. 43. BOAT & CHAIR ISOMERS
  44. 44. Visit us • https://iaanatorg.wixsite.com/welfare • Send us feedback • mailto:iaanat.org@gmail.com • Our page on facebook • iaanat facebook page

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