1. Carbohydrate Chemistry Part 1: Simple Carbohydrates
Dr. Kevin Ahern

2. Nomenclature Structures Cyclizations Modifications Outline
Simple Carbohydrates
Nomenclature
Structures
Cyclizations
Modifications

3. 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

4. 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

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

6. Simple Sugars
Aldopentose
Aldohexose
Ketohexose
Aldohexose
Aldohexose

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

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

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

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

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

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

13. Cyclization of Sugars

14. Cyclization of Sugars

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

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

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

18. Cyclic Structures
Glucose

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

20. Glycosides

21. Sugar Alcohol
Sorbitol (Glucitol)

22. Artificial Sweeteners
Sucralose

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

24. Polysaccharides
Cellulose
Glycogen
Amylose
Amylopectin
Chitin

25. 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