Carbohydrate Chemistry Part 2: Other Carb Carbohydrate Chemistry Part 2: Other Carbohydrates Dr....

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Transcript of Carbohydrate Chemistry Part 2: Other Carb Carbohydrate Chemistry Part 2: Other Carbohydrates Dr....

  • Carbohydrate Chemistry Part 2: Other Carbohydrates

    Dr. Kevin Ahern

  • Nomenclature

    Fischer Form Haworth Form

  • Disaccharides

    • Sucrose (glucose + fructose) • Lactose (glucose + galactose) • Maltose (glucose + glucose)

  • Disaccharides • Comprised of two sugars

    1

    2

    3 4

    5

    6

    1

    2

    3

    4

    5

    6

    Sucrose

    Glucose Fructose

    α1, β2 Diglycosidic Links

    α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside

    Sucrose

    Fructose

    1

    2

    34

    5

    6

    Glucose 1 23

    4

    5

    6

  • Disaccharides • Lactose and Maltose

    Lactose Maltose

    Glucose

    Galactose

    GlucoseGlucose

    1

    1

    2

    2

    3

    3

    4

    4

    5

    5

    6

    6

    β-1,4 Glycosidic Bond

    1 1 22

    3 3

    44

    5 5

    66

    α-1,4 Glycosidic Bond

    β-D-galactopyranosyl-(1→4)-D-glucose α-D-glucopyranosyl-(1→4)-D-glucose

  • Reducing Versus Non-Reducing Sugars

  • Oligosaccharides

    • Found in glycoproteins • Play roles in cellular identity

  • Polysaccharides

    • Cellulose • Glycogen • Amylose • Amylopectin • Chitin

  • Glucose Glucose

    Polysaccharides • Sugar Polymers With Glycosidic Bonds

    Cellulose

    β-1,4 Glycosidic Links

  • Polysaccharides • Sugar Polymers With Glycosidic Bonds

    Glucose Glucose Glucose

    Amylose - component of starch

    α-1-4 Glycosidic Links

    4 44 1 1 1

  • Amylose - component of starch

    Polysaccharides

  • Amylopectin - component of starch

    Glucose Glucose Glucose

    GlucoseGlucose

    α-1,4 Glycosidic Links

    1 1 1444

    α-1,6 Glycοsidic Link Branches

    1 1

    66

    Polysaccharides

  • Polysaccharides • Sugar Polymers With Glycosidic Bonds

    Glycogen

    Glucose Glucose Glucose

    GlucoseGlucose

    α1,4 links

    α1,6 links

  • Modified Polysaccharides

    Chitin Chitin in the wing of a sap beetle

  • Modified Polysaccharides

    Pectin - gelling agent Galacturonic acid polymer α-1,4 bonds

  • Polysaccharides Binding

    Lectins - proteins that bind carbohydrates specifically Part of innate immune system Mannose binding lectin targets microbes

    Phytohemagglutinins in plants Used by bacteria/viruses for cellular attachment Tamiflu inhibits neuraminidase necessary for exit of flu virus

  • Glycolipids • Glycoglycerolipids and Glycosphingolipids

  • Glycolipids • Glycoglycerolipids

    Sugar

    Diacylglycerol

  • Glycolipids • Glycosphingolipids

    Cerebrosides

    Single Sugar Sphingolipid Backbone

  • Glycolipids • Glycosphingolipids

    Gangliosides

    Sphingolipid Backbone

    Complex Carbohydrate

  • Glycosaminoglycans - polyanionic polymers of modified sugars Proteoglycans - peptides/proteins linked to polyanionic polymers of modified sugars Glycoproteins - proteins linked to oligosaccharides N-linked - joined to asparagine in protein - E.R. and Golgi apparatus O-Linked - joined to serine/threonine in protein - Golgi apparatus

    Glycosylation

  • Glycosylation - glycoproteins

  • Glycosylation - Blood typing

  • Glycosaminoglycans • Unbranched polyanionic saccharide polymers

    Chondroitin Sulfate

    Heparin

  • Metabolic Melody

    Structural Lullaby (To the tune of "Brahms' Lullaby")

    Copyright © Kevin Ahern

    In your sleep You can keep

    Learning more about sugars Fischer schemes Haworth rings

    D & L and everything  

    Hydroxides Can’t collide

    Fav’ring chair over boat form Spatial guides

    Coincide With the way structures form

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