Carbohydrate Chemistry Part 2: Other Carbohydrates Dr. Kevin Ahern

Nomenclature Fischer Form Haworth Form

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

Sucrose Sucrose Disaccharides Glucose α1, β2 Diglycosidic Links Comprised of two sugars Sucrose Glucose 1 2 3 4 5 6 α1, β2 Diglycosidic Links 1 2 3 4 5 6 1 2 3 4 5 6 Fructose 1 2 3 4 5 6 Glucose Fructose Sucrose α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside

Disaccharides Glucose Glucose Galactose α-1,4 Glycosidic Bond Lactose and Maltose Glucose Galactose Glucose 1 2 3 4 5 6 β-1,4 Glycosidic Bond 1 2 3 4 5 6 α-1,4 Glycosidic Bond Lactose Maltose β-D-galactopyranosyl-(1→4)-D-glucose α-D-glucopyranosyl-(1→4)-D-glucose

Reducing Versus Non-Reducing Sugars

Found in glycoproteins Play roles in cellular identity Oligosaccharides Found in glycoproteins Play roles in cellular identity

Polysaccharides Cellulose Glycogen Amylose Amylopectin Chitin

Cellulose Polysaccharides β-1,4 Glycosidic Links Glucose Sugar Polymers With Glycosidic Bonds β-1,4 Glycosidic Links Glucose Cellulose

Amylose - component of starch Polysaccharides Sugar Polymers With Glycosidic Bonds α-1-4 Glycosidic Links 4 1 Glucose Amylose - component of starch

Amylose - component of starch Polysaccharides Amylose - component of starch

Amylopectin - component of starch Polysaccharides α-1,6 Glycοsidic Link Branches 1 6 α-1,4 Glycosidic Links 1 4 Glucose Amylopectin - component of starch

Glycogen Polysaccharides α1,6 links α1,4 links Glucose Sugar Polymers With Glycosidic Bonds α1,4 links Glucose Glycogen

Modified Polysaccharides Chitin in the wing of a sap beetle Chitin

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

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

Sphingolipid Backbone Glycolipids Glycosphingolipids Single Sugar Sphingolipid Backbone Cerebrosides

Sphingolipid Backbone Glycolipids Complex Carbohydrate Glycosphingolipids Sphingolipid Backbone Gangliosides

Glycosylation 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 - glycoproteins

Glycosylation - Blood typing

Chondroitin Sulfate Heparin Glycosaminoglycans Unbranched polyanionic saccharide polymers Heparin

Structural Lullaby In your sleep You can keep (To the tune of "Brahms' Lullaby") Copyright © Kevin Ahern Metabolic Melody 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