CarbohydrateChemistryPart1:SimpleCarbohydrates
Dr.KevinAhern
Outline
• Nomenclature• Structures• Cyclizations• Modifications
SimpleCarbohydrates
Saccharides
Monosaccharides
Saccharides
Monosaccharides
• Cx(H2O)x• Glucose(C6H12O6)
• Fructose(C6H12O6)
• Ribose(C5H10O5)
• Galactose(C6H12O6)
• Glyceraldehyde(C3H6O3)
Saccharides
Monosaccharides
• Cx(H2O)x• Glucose(C6H12O6)
• Fructose(C6H12O6)
• Ribose(C5H10O5)
• Galactose(C6H12O6)
• Glyceraldehyde(C3H6O3)
X =
Saccharides
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 =
Saccharides
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
Saccharides
DifferentSizesThe-oses
D-GlyceraldehydeD-Threose
D-Ribose
D-Glucose
DifferentSizesThe-oses
D-GlyceraldehydeD-Threose
D-Ribose
D-Glucose
3 Carbons
Triose
DifferentSizesThe-oses
D-GlyceraldehydeD-Threose
D-Ribose
D-Glucose
3 Carbons
Triose
4 Carbons
Tetrose
DifferentSizesThe-oses
D-GlyceraldehydeD-Threose
D-Ribose
D-Glucose
3 Carbons
Triose
4 Carbons
Tetrose
5 Carbons
Pentose
DifferentSizesThe-oses
D-GlyceraldehydeD-Threose
D-Ribose
D-Glucose
3 Carbons
Triose
4 Carbons
Tetrose
5 Carbons
Pentose
6 Carbons
Hexose
CommonSugarsAldoseandKetose
CommonSugarsAldoseandKetose
D-Glucose
CommonSugarsAldoseandKetose
D-Glucose D-Fructose
CommonSugarsAldoseandKetose
D-Glucose D-Fructose
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CommonSugarsAldoseandKetose
D-Glucose D-Fructose
AldehydeKetone
CommonSugarsAldoseandKetose
D-Glucose D-Fructose
AldehydeKetone
Aldose Ketose
SimpleSugars
SimpleSugars
Aldopentose
SimpleSugars
Aldopentose Aldohexose
SimpleSugars
Aldopentose Aldohexose Ketohexose
SimpleSugars
Aldopentose Aldohexose Ketohexose Aldohexose
SimpleSugars
Aldopentose Aldohexose Ketohexose Aldohexose Aldohexose
SimpleSugars
Aldopentose Aldohexose Ketohexose Aldohexose Aldohexose
AsymmetricCarbonsTheGlyceraldehydes
AsymmetricCarbonsTheGlyceraldehydes Asymmetric
PenultimateCarbon
AsymmetricCarbonsTheGlyceraldehydes Asymmetric
PenultimateCarbon
L- Configuration
AsymmetricCarbonsTheGlyceraldehydes Asymmetric
PenultimateCarbon D- Configuration
L- Configuration
AsymmetricCarbonsTheGlyceraldehydes Asymmetric
PenultimateCarbon D- Configuration
L- ConfigurationMirror Images
AsymmetricCarbonsTheGlyceraldehydes Asymmetric
PenultimateCarbon D- Configuration
L- Configuration
L-Glyceraldehyde D-Glyceraldehyde
MultipleAsymmetricCenters• Glucose
D-Glucose
MultipleAsymmetricCenters• Glucose
D-Glucose
Asymmetric Carbons
MultipleAsymmetricCenters• Glucose
D-Glucose
D-configuration
Enantiomers• Mirror Images
D-Glucose L-Glucose
Enantiomers• Mirror Images
D-Glucose L-Glucose
D-configuration
Enantiomers• Mirror Images
D-Glucose L-Glucose
D-configuration L-configuration
Diastereomers• Same chemical type & size, non-mirror images
D-Glucose D-Gulose
Diastereomers• Same chemical type & size, non-mirror images
D-Glucose D-Gulose
Same Configuration
Same Configuration
Diastereomers• Same chemical type & size, non-mirror images
D-Glucose D-Gulose
Same Configuration
Same Configuration
Different Configurations
Epimers• Diastereomers differing in configuration of one carbon only
D-Glucose D-Galactose
CyclizationofSugars
In Close Spatial Proximity
CyclizationofSugars
CyclizationofSugars
New Asymmetric Center
CyclizationofSugars
New Asymmetric Center
The New Asymmetric Carbon Is Called Anomeric
CyclizationofSugars
CyclizationofSugars
CyclizationofSugars
CyclizationofSugars
HaworthStructures• Glucose
α-D-Glucopyranose β-D-Glucopyranose
HaworthStructures• Glucose
α-D-Glucopyranose β-D-Glucopyranose
HaworthStructures• Glucose
α-D-Glucopyranose
Anomers
β-D-Glucopyranose
CommonFuranoses• Fructose and Ribose
β-D-Fructofuranose β-D-Ribofuranose
ConformationalIsomers• Chair and Boat Forms of β-D-Glucose
ConformationalIsomers• Chair and Boat Forms of β-D-Glucose
CyclicStructures• Glucose
ModifiedSugars
Galactosamine N-acetylglucosamine Mannose-6-phosphate
Fructose-1,6-bisphosphate Glucuronic Acid
Glycosides
SugarAlcohol
Sorbitol (Glucitol)
ArtificialSweeteners
Sucralose
Disaccharides
• Sucrose(glucose+fructose)• Lactose(glucose+galactose)• Maltose(glucose+glucose)
Polysaccharides
• Cellulose• Glycogen• Amylose• Amylopectin• Chitin
MetabolicMelody
Hark the Sucrose(to the tune of "Hark the Herald")
Copyright © Kevin Ahern
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
Alpha, beta, D and L Di-astere-omer hell