Carbs
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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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Carbs

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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

    • Storage, energy modules, metabolic intermediates

  • Disaccharides, trisaccharides

    • Storage

  • Oligosaccharides

    • Molecular Recognition

  • Polysaccharides

    • Structure, storage


Fisher Projectionsof chiral monosaccharides

  • Next-to-bottom carbon hydroxyl extends to the right --- a D sugar; cf. with L amino acid


fig 9-3a


fig 9-3b


Hemiacetal/-ketal structures of monosaccharides

  • Reaction of an aldehyde or ketone with an alcohol

    • favorable intramolecular reaction


fig 9-5


Intramolecular hemiacetals/ketals of monosaccharides are RINGS

stereo

chair

open chain

Haworth


Anomers

  • Sugars that vary in configuration about the anomeric (aldehydic or ketonic) carbon

  • Convention:  = hydroxyl down,

     = hydroxyl up


fig 9-6


Fig 9-7


Hexose derivatives

  • Amino sugars

    • Acetamido sugars

  • Deoxy sugars

    • Fucose, rhamnose, abequose

  • Other glycosidic additives

    • Lactic acid

  • Oxidized sugars

  • Sugar phosphates


Fig 9-9


Reducing sugars

  • Aldehydes are oxidized by mild agents

    • Cu2+ + aldehyde (or -hydroxyketone)  Cu+ + acid

  • Disaccharides react more slowly


Fig 9-10


Disaccharides

  • Glycosidic linkage

    • Acetal (or ketal) formed. 2nd monosaccharide acts as an alcohol


Fig 9-5 (repeat)


Disaccharide, cont

  • Reducing

    • one anomeric C not glycosidically linked

  • Nonreducing

    • Both anomeric C’s linked (fructose, trehalose)


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)


Fig 9-11


Table 9-1


Important disaccharides

  • Maltose

  • Lactose

  • Sucrose

  • Trehalose


Fig 9-12


Table 9-2


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 9-15 b


Fig 9-14

0.10 m

1.0 m


fig 9-15


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

Cellulose

Chitin


Structural polysaccharides, cont

  • Bacterial cell walls – peptidoglycans

  • Extracellular matrix of multicellular animals - glycosaminoglycans


Fig 9-19


Fig 9-20


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)


Fig 9-29


Fig 9-27


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