Carbohydrate Structure Biochemistry Free For All

Nomenclature Structures Cyclizations Modifications Outline Simple Carbohydrates Nomenclature Structures Cyclizations Modifications

Saccharides X = Aldehydes = Aldoses Ketones = Ketoses Cx(H2O)x Monosaccharides Cx(H2O)x Glucose (C6H12O6) Fructose (C6H12O6) Ribose (C5H10O5) Galactose (C6H12O6) Glyceraldehyde (C3H6O3) • Tri- = 3 • Tetr- = 4 • Pent- = 5 • Hex- =6 • Hept- = 7 • Oct- = 8 X = Aldehydes = Aldoses Ketones = Ketoses

Different Sizes 3 Carbons Triose 4 Carbons Tetrose 5 Carbons Pentose The -oses 3 Carbons Triose 4 Carbons Tetrose 5 Carbons Pentose 6 Carbons Hexose D-Glyceraldehyde D-Threose D-Ribose D-Glucose

{ } Aldose Ketose Common Sugars Aldehyde Ketone D-Glucose D-Fructose Aldose and Ketose Aldehyde Ketone D-Glucose D-Fructose { } Aldose Ketose

Simple Sugars Aldopentose Aldohexose Ketohexose Aldohexose Aldohexose

Mirror Images L-Glyceraldehyde D-Glyceraldehyde Asymmetric Carbons Penultimate Carbon The Glyceraldehydes D- Configuration L- Configuration Mirror Images L-Glyceraldehyde D-Glyceraldehyde

Multiple Asymmetric Centers Glucose D-configuration Asymmetric Carbons D-Glucose

Enantiomers D-configuration L-configuration D-Glucose L-Glucose Mirror Images D-configuration L-configuration D-Glucose L-Glucose

Diastereomers Same Configuration D-Glucose D-Gulose Different Same chemical type & size, non-mirror images Same Configuration D-Glucose D-Gulose Different Configurations

Epimers D-Glucose D-Galactose Diastereomers differing in configuration of one carbon only D-Glucose D-Galactose

The New Asymmetric Carbon Cyclization of Sugars New Asymmetric Center In Close Spatial Proximity The New Asymmetric Carbon Is Called Anomeric

Cyclization of Sugars

Cyclization of Sugars

Haworth Structures Glucose Anomers α-D-Glucopyranose β-D-Glucopyranose

Common Furanoses β-D-Fructofuranose β-D-Ribofuranose Fructose and Ribose β-D-Fructofuranose β-D-Ribofuranose

Conformational Isomers Chair and Boat Forms of β-D-Glucose

Cyclic Structures Glucose

Fructose-1,6-bisphosphate Modified Sugars Galactosamine N-acetylglucosamine Mannose-6-phosphate Fructose-1,6-bisphosphate Glucuronic Acid

Glycosides

Sugar Alcohol Sorbitol (Glucitol)

Artificial Sweeteners Sucralose

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

Polysaccharides Cellulose Glycogen Amylose Amylopectin Chitin

Hark the Sucrose (to the tune of "Hark the Herald") Copyright © Kevin Ahern Metabolic Melody Carbohydrates all should sing Glory to the Haworth ring Anomeric carbons hide When they're in a glycoside Glucopyranose is there In the boat or in the chair Alpha, beta, D and L Di-astere-omer hell

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 Peptidoglycans - 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