Carbohydrate Chemistry Part 1: Simple Carbohydrates

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Presentation transcript:

Carbohydrate Chemistry Part 1: Simple Carbohydrates Dr. Kevin Ahern

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