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Carbs. Greatest biomass of biopolymers Polyhydroxy aldehydes and ketones Many functions Structure. Fuel Energy storage Adhesion Lubrication signalling tagging for siting, function. Carbohydrates. Degree of polymerization. Monosaccharides

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carbohydrates
Greatest biomass of biopolymers

Polyhydroxy aldehydes and ketones

Many functions

Structure

Fuel

Energy storage

Adhesion

Lubrication

signalling

tagging for siting, function

Carbohydrates
degree of polymerization
Degree of polymerization
  • Monosaccharides
    • Storage, energy modules, metabolic intermediates
  • Disaccharides, trisaccharides
    • Storage
  • Oligosaccharides
    • Molecular Recognition
  • Polysaccharides
    • Structure, storage
fisher projections of chiral monosaccharides
Fisher Projectionsof chiral monosaccharides
  • Next-to-bottom carbon hydroxyl extends to the right --- a D sugar; cf. with L amino acid
hemiacetal ketal structures of monosaccharides
Hemiacetal/-ketal structures of monosaccharides
  • Reaction of an aldehyde or ketone with an alcohol
    • favorable intramolecular reaction
anomers
Anomers
  • Sugars that vary in configuration about the anomeric (aldehydic or ketonic) carbon
  • Convention:  = hydroxyl down,

 = hydroxyl up

hexose derivatives
Hexose derivatives
  • Amino sugars
    • Acetamido sugars
  • Deoxy sugars
    • Fucose, rhamnose, abequose
  • Other glycosidic additives
    • Lactic acid
  • Oxidized sugars
  • Sugar phosphates
reducing sugars
Reducing sugars
  • Aldehydes are oxidized by mild agents
    • Cu2+ + aldehyde (or -hydroxyketone)  Cu+ + acid
  • Disaccharides react more slowly
disaccharides
Disaccharides
  • Glycosidic linkage
    • Acetal (or ketal) formed. 2nd monosaccharide acts as an alcohol
disaccharide cont
Disaccharide, cont
  • Reducing
    • one anomeric C not glycosidically linked
  • Nonreducing
    • Both anomeric C’s linked (fructose, trehalose)
disaccharide nomenclature
Disaccharide nomenclature
  • Nonreducing end on left
  • Linkage –(nm)-
  • Reducing end

Note that nonreducing end configuration is fixed

Reducing end can mutarotate, thus 1st component given as - or -, 2nd ambiguous (next slide)

important disaccharides
Important disaccharides
  • Maltose
  • Lactose
  • Sucrose
  • Trehalose
storage polysaccharides
Storage polysaccharides
  • Plants
    • Starch
      • Amylose – llinear polyglucose, -1,4 linked (-D-glucopyranosyl-(14)-…), M ~ 106
      • Amylopectin –polyglucose, -1,4 linked, -1,6 branched 1 per 24-30, M ~ 108
  • Animals
    • Glycogen
      • polyglucose, -1,4 linked, -1,6 branched 1 per 24-30, M ~ 106
fig 9 14
Fig 9-14

0.10 m

1.0 m

structural polysaccharides
Structural Polysaccharides
  • Plants
    • Cellulose – linear polyglucose
    •  1,4 linked
    • M ~ 106
  • Certain exoskeletons
    • Chitin – linear poly(N-acetyl-D-glucosamine)
    •  1,4 linked
fig 9 17a and 9 18
Fig 9-17a and 9-18

Cellulose

Chitin

structural polysaccharides cont
Structural polysaccharides, cont
  • Bacterial cell walls – peptidoglycans
  • Extracellular matrix of multicellular animals - glycosaminoglycans
sugar protein and sugar lipid conjugates
Sugar-protein and sugar-lipid conjugates
  • Glycoconjugates
    • Proteoglycans
      • Glycosaminoglycans bound to proteins
    • Glycoproteins
      • Oligosaccharides bound to proteins
    • Glycolipids
      • Oligosaccharides bound to lipids (heads of membrane lipids)
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