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Carbohydrates
Carbohydrates
 Most

abundant class of biological molecules on

Earth
 Originally

produced through CO2 fixation during
...
Roles of Carbohydrates
 Energy

storage (glycogen,starch)

 Structural
 Cellular

components (cellulose,chitin)

recogn...
Carbohydrates
 Monosaccharides

(simple sugars) cannot be broken

down into simpler sugars under mild conditions
 Oligos...
Monosaccharides
 Polyhydroxy

ketones (ketoses) and aldehydes

(aldoses)
 Aldoses

and ketoses contain aldehyde and keto...
 Ketose

named for “equivalent aldose” + “ul”

inserted
 Triose,

tetrose, etc. denotes number of carbons

 Empirical

...
Monosaccharides are chiral
 Aldoses

with 3C or more and ketoses with 4C or more

are chiral
 The

number of chiral carb...
Stereochemistry
 Enantiomers
 Pairs

= mirror images

of isomers that have opposite configurations at

one or more chiral centers but ar...
Cyclization of aldose and ketoses
introduces additional chiral center
 Aldose

sugars (glucose) can cyclize to form a
cyc...
•Ketose sugars (fructose) can cyclize to form a
cyclic hemiketal
Haworth Projections
O

H

-OH up = beta
-OH down = alpha

C1
H

C2

OH

HO

C3

H

H

C4

OH

H

C5

OH

CH2OH

6
5
4

1
3...
Monosaccharides can cyclize to form
Pyranose / Furanose forms
a = 64%
b = 36%

a = 21.5%
b = 58.5%

a = 13.5%
b = 6.5%
Conformation of Monosaccharides

Pyranose sugars not planar molecules, prefer to be in
either of the two chair conformatio...
Reducing Sugars
 When

in the uncyclized form, monosaccharides act

as reducing agents.
 Free

carbonyl group from aldos...
Derivatives
of
Monosaccharides
Sugar Phosphates
Deoxy Acids
Amino Sugars
Sugar alcohols
Monosaccharide structures you
need to know


Glucose



Fructose



Ribulose



Glyceraldehyde



Dihydroxyacetone
Introduction carbohydrates
Introduction carbohydrates
Introduction carbohydrates
Introduction carbohydrates
Introduction carbohydrates
Introduction carbohydrates
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Introduction carbohydrates

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Introduction carbohydrates

  1. 1. Carbohydrates
  2. 2. Carbohydrates  Most abundant class of biological molecules on Earth  Originally produced through CO2 fixation during photosynthesis
  3. 3. Roles of Carbohydrates  Energy storage (glycogen,starch)  Structural  Cellular components (cellulose,chitin) recognition  Carbohydrate derivatives include DNA, RNA, co- factors, glycoproteins, glycolipids
  4. 4. Carbohydrates  Monosaccharides (simple sugars) cannot be broken down into simpler sugars under mild conditions  Oligosaccharides  Polysaccharides = "a few" - usually 2 to 10 are polymers of the simple sugars
  5. 5. Monosaccharides  Polyhydroxy ketones (ketoses) and aldehydes (aldoses)  Aldoses and ketoses contain aldehyde and ketone functions, respectively
  6. 6.  Ketose named for “equivalent aldose” + “ul” inserted  Triose, tetrose, etc. denotes number of carbons  Empirical formula = (CH2O)n
  7. 7. Monosaccharides are chiral  Aldoses with 3C or more and ketoses with 4C or more are chiral  The number of chiral carbons present in a ketose is always one less than the number found in the same length aldose  Number of possible steroisomers = 2n (n = the number of chiral carbons)
  8. 8. Stereochemistry
  9. 9.  Enantiomers  Pairs = mirror images of isomers that have opposite configurations at one or more chiral centers but are NOT mirror images are diastereomers  Epimers = Two sugars that differ in configuration at only one chiral center
  10. 10. Cyclization of aldose and ketoses introduces additional chiral center  Aldose sugars (glucose) can cyclize to form a cyclic hemiacetal
  11. 11. •Ketose sugars (fructose) can cyclize to form a cyclic hemiketal
  12. 12. Haworth Projections O H -OH up = beta -OH down = alpha C1 H C2 OH HO C3 H H C4 OH H C5 OH CH2OH 6 5 4 1 3 2 Anomeric carbon (most oxidized) For all non-anomeric carbons, -OH groups point down in Haworth projections if pointing right in Fischer projections
  13. 13. Monosaccharides can cyclize to form Pyranose / Furanose forms a = 64% b = 36% a = 21.5% b = 58.5% a = 13.5% b = 6.5%
  14. 14. Conformation of Monosaccharides Pyranose sugars not planar molecules, prefer to be in either of the two chair conformations.
  15. 15. Reducing Sugars  When in the uncyclized form, monosaccharides act as reducing agents.  Free carbonyl group from aldoses or ketoses can reduce Cu2+ and Ag+ ions to insoluble products
  16. 16. Derivatives of Monosaccharides
  17. 17. Sugar Phosphates
  18. 18. Deoxy Acids
  19. 19. Amino Sugars
  20. 20. Sugar alcohols
  21. 21. Monosaccharide structures you need to know  Glucose  Fructose  Ribulose  Glyceraldehyde  Dihydroxyacetone

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