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

Carbs


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


Fig 9 3a

fig 9-3a


Fig 9 3b

fig 9-3b


Hemiacetal ketal structures of monosaccharides

Hemiacetal/-ketal structures of monosaccharides

  • Reaction of an aldehyde or ketone with an alcohol

    • favorable intramolecular reaction


Fig 9 5

fig 9-5


Intramolecular hemiacetals ketals of monosaccharides are rings

Intramolecular hemiacetals/ketals of monosaccharides are RINGS

stereo

chair

open chain

Haworth


Anomers

Anomers

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

  • Convention:  = hydroxyl down,

     = hydroxyl up


Fig 9 6

fig 9-6


Fig 9 7

Fig 9-7


Hexose derivatives

Hexose derivatives

  • Amino sugars

    • Acetamido sugars

  • Deoxy sugars

    • Fucose, rhamnose, abequose

  • Other glycosidic additives

    • Lactic acid

  • Oxidized sugars

  • Sugar phosphates


Fig 9 9

Fig 9-9


Reducing sugars

Reducing sugars

  • Aldehydes are oxidized by mild agents

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

  • Disaccharides react more slowly


Fig 9 10

Fig 9-10


Disaccharides

Disaccharides

  • Glycosidic linkage

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


Fig 9 5 repeat

Fig 9-5 (repeat)


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)


Fig 9 11

Fig 9-11


Table 9 1

Table 9-1


Important disaccharides

Important disaccharides

  • Maltose

  • Lactose

  • Sucrose

  • Trehalose


Fig 9 12

Fig 9-12


Table 9 2

Table 9-2


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 15 b

Fig 9-15 b


Fig 9 14

Fig 9-14

0.10 m

1.0 m


Fig 9 15

fig 9-15


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


Fig 9 19

Fig 9-19


Fig 9 20

Fig 9-20


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)


Fig 9 29

Fig 9-29


Fig 9 27

Fig 9-27


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