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CH 2 OH. O. H. H. H. OH. H. OH. HO. H. OH. Carbohydrates -I- . Energy molecules. General Characteristics . Carbohydrates = Carbon (C) + Hydrates (OH). All carbohydrates are compounds composed of (at least) C, H, and O The general formula for a carbohydrate is: (CH 2 O) n

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carbohydrates i

CH2OH

O

H

H

H

OH

H

OH

HO

H

OH

Carbohydrates -I-

Energy molecules

slide2

General Characteristics

  • Carbohydrates = Carbon (C) + Hydrates (OH).
  • All carbohydrates are compounds composed of (at least) C, H, and O
  • The general formula for a carbohydrate is: (CH2O)n
  • Not all carbohydrates have this empirical formula (e.g. deoxysugars, aminosugars, etc.)
  • Carbohydrates are the most abundant compounds found in nature.
  • Produced by photosynthesis in plants from CO2, H2O and energy.
  • Are oxidized in living cells (respiration) to produce CO2, H2O, and energy.
carbohydrate functions
Carbohydrate Functions

Carbohydrates can be:

  • Sources of energy
  • Intermediates in the biosynthesis of other basic biomolecules (fats and proteins)
  • Structural tissues in plants and in microorganisms (cellulose, lignin, murein)
  • Involved in biological transport, cell-cell recognition, activation of growth factors, modulation of the immune system
classification
Classification:

Carbohydrates are placed in to one of three categories, depending on the number of monosaccharide units, or residues, they contain.

  • Monosaccharides, contain a single monosaccharide residue.
  • Oligosaccharides, contain 2 to 10 monosaccharide residues.
    • These include the disaccharides, which contain 2 monosaccharide residues.
  • Polysaccharides, which contain more than 10 monosaccharide residues.
    • These may contain thousands of monosaccharide residues.
monosaccharides
Monosaccharides
  • Monosaccharides are polyhydroxyaldehydes or ketones.
  • Monosaccharides contain 3 to 7 carbon atoms.
monosaccharides7
Monosaccharides

Monosaccharides are classified according to the number of carbons and whether they contain an aldehyde or ketone.

  • The “-ose” ending is used to designate carbohydrates.
monosaccharides8
Monosaccharides

Monosaccharides contain chiral carbon atoms.

  • This is what accounts for the large number of different monosaccharides.
  • For each chiral carbon, n, a monosaccharide has 2nstereoisomers.
    • These will be divided among 2n/2 pairs of enantiomers.
  • Glucose contains 4 chiral carbons
  • Glucose has 24 = 16 stereoisomers
  • These stereoisomers can be grouped into 16/2 = 8 pairs of enantiomers.
monosaccharides9

Fischer projection:

Monosaccharides

Fischer projections are used to distinguish the different stereoisomers.

  • The letters D and L are used to distinguish between the members of a pair of enantiomers.
    • The D or L designation is based on the chiral carbon furthest from the carbonyl carbon.
monosaccharides10
Monosaccharides

Important monosaccharides.

  • pentoses and hexoses are the most abundant

Pentoses

  • D-ribose and D-2-deoxyribose are found in DNA, RNA and nucleotides such as FADH2 and NADH
epimers
Epimers
  • Pairs of monosaccharides different only inconfiguration around only one specific C-atom.
  • For example, glucose and galactose are C-4 epimers—their structures differ only in the position of the -OH group at carbon 4.
monosaccharides12
Monosaccharides

Important monosaccharides.

Hexoses

  • D-glucose (dextrose or blood surgar) - major metabolite and storage form of chemical energy.
  • D-galactose - combines with glucose to produce lactose (milk sugar)
  • D-fructose (fruit sugar) - major metabolite and sweetest tasting natural sugar.
    • fructose is a ketose
monosaccharides13
Monosaccharides

Monosaccharide derivatives

  • Amino sugars.
    • One or more -OH’s are replaced with -NH2’s
    • Often these are acetylated to form amides.

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monosaccharides14
Monosaccharides

Monosaccharide derivatives

  • Carboxylic acid sugars.
    • The ketone, aldehyde, or primary alcohol is oxidized to a carboxylic acid.
question

β-D-sorbofuranose

α-D-sorbofuranose

Question:

Shown below is the Fischer projection for sorbose

Is the structure shown

  • D-sorbose
  • L-sorbose

Draw and name the α and β ring forms for sorbose

question16

α-L-galactopyranose

β-L-galactopyranose

Question:

Shown to the right is the Fischer projection for galactose

Is the structure shown

  • D-galactose
  • L-galactose

Draw and name the α and β ring forms for galactose

slide17
إن الله وملائكتــه يصلــون على النبي يــأيــها الذيـن آمنوا صلــوا عليه وسلمـــوا تسليمـــا