CARBOHYDRATE CHEMISTRY
INTRODUCTION TO
CARBOHYDRATES
Monosaccharides
INTRODUCTION
 Carbohydrates are one of the three major
classes of biological molecules.
 Carbohydrates are also the most...
FUNCTIONS
 Variety of important functions in living
systems:
nutritional (energy storage, fuels,
metabolic intermediates...
 Carbohydrates also can combine with
lipids to form glycolipids
OR
 With proteins to form glycoproteins.
Carbohydrates are chemically
characterized as:
Poly hydroxy aldehydes or
Poly hydroxy ketones.
 Sugars that contain an aldehyde group
are called Aldoses.
 Sugars that contain a keto group are
called Ketoses.
IMPORTANT TERMS REGARDING
CHO
 Asymmetric carbon
 Symmetric carbon
 Carbonyl carbon
 Reference carbon
 Anomeric carbon
ASYMMETRIC CARBON
 A carbon linked to four different atoms or
groups farthest from the carbonyl carbon
 Also called Chir...
ISOMERS
 Isomers are molecules that have the same
molecular formula, but have a different
arrangement of the atoms in spa...
ISOMER 1
Examples of isomers:
1. Glucose
2. Fructose
3. Galactose
4. Mannose
Same chemical formula C6 H12 O6
EPIMERS
 EPIMERS are sugars that differ in
configuration at ONLY 1 POSITION.
 Examples of epimers :
D-glucose & D-galac...
ENANTIOMERS
Non-Superimposable COMPLETE mirror
image (differ in configuration at EVERY
CHIRAL CENTER.
 The two members of the pair are
designated as D and L forms.
 In D form the OH group on the
asymmetric carbon is on the...
CYCLIZATION
 Less then 1%of CHO exist in an open
chain form.
 Predominantly found in ring form.
 involving reaction of ...
 Six membered ring structures are called
Pyranoses .
 five membered ring structures are called
Furanoses .
Straight
chain
Haworth
projection
chair
Hemiacetal;reaction
between aldehyde and
hydroxy grp.
GLUCOSE
ANOMERIC CARBON
 The carbonyl carbon after cyclization becomes
the anomeric carbon.
 This creates α and β configuration....
 Such α and β configuration are called
diastereomers and they are not mirror images.
Enzymes can distinguished between th...
MUTAROTATION
 Unlike the other stereoisomeric forms, α
and β anomers spontaneously
interconvert in solution.
 This is ca...
OPTICAL ACTIVITY
 When a plane polarized light is passed through a
solution containing monosaccharides the light
will eit...
REDUCING SUGAR
 Sugars in which the oxygen of the
anomeric carbon is free and not attached
to any other structure, such s...
CLASSIFICATION
All carbohydrates can be classified as
either:
 Monosaccharides
 Disaccharides
 oligosaccharides or Poly...
 Monosaccharides- one unit of
carbohydrate
 Disaccharides- Two units of
carbohydrates.
 Anywhere from two to ten monosa...
1.Monosaccharides
The monosaccharide commonly found in humans are classified
according to the number of carbons they conta...
Pentoses of Physiologic Importance.
Sugar Source Biochemical and Clinical Importance
D-Ribose Nucleic acids and
metabolic ...
Hexoses of Physiologic Importance.
Sugar Source Biochemical Importance Clinical Significance
D-Glucose Fruit juices, hydro...
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
Intro to cho and monosaccharides
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Intro to cho and monosaccharides

  1. 1. CARBOHYDRATE CHEMISTRY INTRODUCTION TO CARBOHYDRATES Monosaccharides
  2. 2. INTRODUCTION  Carbohydrates are one of the three major classes of biological molecules.  Carbohydrates are also the most abundant biological molecules.  Carbohydrates derive their name from the general formula Cn (H2O).
  3. 3. FUNCTIONS  Variety of important functions in living systems: nutritional (energy storage, fuels, metabolic intermediates) structural (components of nucleotides, plant and bacterial cell walls, arthropod exoskeletons, animal connective tissue)  informational (cell surface of eukaryotes -- molecular recognition, cell-cell communication)
  4. 4.  Carbohydrates also can combine with lipids to form glycolipids OR  With proteins to form glycoproteins.
  5. 5. Carbohydrates are chemically characterized as: Poly hydroxy aldehydes or Poly hydroxy ketones.
  6. 6.  Sugars that contain an aldehyde group are called Aldoses.  Sugars that contain a keto group are called Ketoses.
  7. 7. IMPORTANT TERMS REGARDING CHO  Asymmetric carbon  Symmetric carbon  Carbonyl carbon  Reference carbon  Anomeric carbon
  8. 8. ASYMMETRIC CARBON  A carbon linked to four different atoms or groups farthest from the carbonyl carbon  Also called Chiral carbon
  9. 9. ISOMERS  Isomers are molecules that have the same molecular formula, but have a different arrangement of the atoms in space. (different structures).
  10. 10. ISOMER 1
  11. 11. Examples of isomers: 1. Glucose 2. Fructose 3. Galactose 4. Mannose Same chemical formula C6 H12 O6
  12. 12. EPIMERS  EPIMERS are sugars that differ in configuration at ONLY 1 POSITION.  Examples of epimers : D-glucose & D-galactose (epimeric at C4) D-glucose & D-mannose (epimeric at C2) D-idose & L-glucose (epimeric at C5)
  13. 13. ENANTIOMERS Non-Superimposable COMPLETE mirror image (differ in configuration at EVERY CHIRAL CENTER.
  14. 14.  The two members of the pair are designated as D and L forms.  In D form the OH group on the asymmetric carbon is on the right.  In L form the OH group is on the left side.  D-glucose and L-glucose are enantiomers:
  15. 15. CYCLIZATION  Less then 1%of CHO exist in an open chain form.  Predominantly found in ring form.  involving reaction of C-5 OH group with the C-1 aldehyde group or C-2 of keto group.
  16. 16.  Six membered ring structures are called Pyranoses .  five membered ring structures are called Furanoses .
  17. 17. Straight chain Haworth projection chair Hemiacetal;reaction between aldehyde and hydroxy grp. GLUCOSE
  18. 18. ANOMERIC CARBON  The carbonyl carbon after cyclization becomes the anomeric carbon.  This creates α and β configuration.  In α configuration the OH is on the same of the ring in fischer projection. In Haworths it is on the trans side of CH2OH.
  19. 19.  Such α and β configuration are called diastereomers and they are not mirror images. Enzymes can distinguished between these two forms:  Glycogen is synthesized from α-D glucopyranose  Cellulose is synthesized from β -D glucopyranose
  20. 20. MUTAROTATION  Unlike the other stereoisomeric forms, α and β anomers spontaneously interconvert in solution.  This is called mutarotation.
  21. 21. OPTICAL ACTIVITY  When a plane polarized light is passed through a solution containing monosaccharides the light will either be rotated towards right or left.  This rotation is because of the presence of asymmetric carbon atom.  If it is rotated towards left- levorotatory (-)  If it is rotated towards right- dextrorotatory(+)
  22. 22. REDUCING SUGAR  Sugars in which the oxygen of the anomeric carbon is free and not attached to any other structure, such sugars can act as reducing agents and are called reducing sugars.
  23. 23. CLASSIFICATION All carbohydrates can be classified as either:  Monosaccharides  Disaccharides  oligosaccharides or Polysaccharides.
  24. 24.  Monosaccharides- one unit of carbohydrate  Disaccharides- Two units of carbohydrates.  Anywhere from two to ten monosaccharide units, make up an oligosaccharide.  Polysaccharides are much larger, containing hundreds of monosaccharide units.
  25. 25. 1.Monosaccharides The monosaccharide commonly found in humans are classified according to the number of carbons they contain in their backbone structures. Classifications Trioses (C3 H6 O3 ) Glycerose (glyceraldehyde) Dihydroxyacetone Tetroses (C4 H8 O4 ) Erythrose Erythrulose Pentoses (C5 H10 O5 ) Ribose Ribulose Hexoses (C6 H12 O6 ) Glucose Fructose Heptoses (C7 H14 O7 ) — Sedoheptulose ALDOSES KETOSES
  26. 26. Pentoses of Physiologic Importance. Sugar Source Biochemical and Clinical Importance D-Ribose Nucleic acids and metabolic intermediate Structural component of nucleic acids and coenzymes, including ATP, NAD(P), and flavin coenzymes D-Ribulose Metabolic intermediate Intermediate in the pentose phosphate pathway D-Arabinose Plant gums Constituent of glycoproteins D-Xylose Plant gums, proteoglycans, glycosaminoglycans Constituent of glycoproteins L-Xylulose Metabolic intermediate Excreted in the urine in essential pentosuria
  27. 27. Hexoses of Physiologic Importance. Sugar Source Biochemical Importance Clinical Significance D-Glucose Fruit juices, hydrolysis of starch, cane or beet sugar, maltose and lactose The main metabolic fuel for tissues; "blood sugar" Excreted in the urine (glucosuria) in poorly controlled diabetes mellitus as a result of hyperglycemia D-Fructose Fruit juices, honey, hydrolysis of cane or beet sugar and inulin, enzymic isomerization of glucosesyrups for food manufacture Readily metabolized either via glucoseor directly Hereditary fructose intolerance leads to fructose accumulation and hypoglycemia D-Galactose Hydrolysis of lactose Readily metabolized to glucose; synthesized in the mammary gland for synthesis of lactose in milk. A constituent of glycolipids and glycoproteins Hereditary galactosemia as a result of failure to metabolize galactose leads to cataracts D-Mannose Hydrolysis of plant mannan gums Constituent of glycoproteins

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