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Monosaccharides
Simplest carbohydrates; single sugar molecule
Number of stereoisomers: 2n
Where n = # of chiral carbons
Carbohydrate composition
Disaccharides
Linked by O-glycosidic bond
Interaction between the anomeric carbon
(electrophile) and the lone pair e- (nucleophile)
from the primary alcohol
Reducing disaccharide is produced if there is one
free anomeric carbon outside of the glycosidic bond
Carbohydrate composition
Oligosaccharides
Carbohydrates that have 2-10 sugar molecules
glycoproteins, glycolipids
Carbohydrate composition
Polysaccharides
Carbohydrates that have more than 10 sugar
molecules
Storage polysaccharides: glycogen, starch
Monosaccharides
Monosaccharide classification:
Aldoses: terminal aldehyde
Ketoses: keto-group (position-dependent)
Both are functional isomers
Both contain a primary alcohol attached to the last
carbon
Monosaccharides
Monosaccharides
Simplest aldose: D-glyceraldehyde
Simplest ketose: dihydroxyacetone
Fischer projection:
Monosaccharides
Epimers:
D-glucose and D-mannose are 2-epimers
D-glucose and D-galactose are 4-epimers
Fischer projection:
Hemiacetals and Hemiketals
Hemi half
Formed by addition of alcohol (nucleophile) to
the carbonyl (electrophile)
Responsible for the formation of the closed
chain configuration of saccharides
Pyranose and furanose
Hemiacetals and Hemiketals
Monosaccharides
Pyranose (6-membered ring) or furanose (5-membered ring)
glucose (dextrose), fructose, galactose
glucopyranose, fructofuranose, galactopyranose
Haworth projection:
Monosaccharides
5 C sugars furanose
Ribose and xylose -> ribofuranose and xylofuranose
Haworth projection:
Anomers
Differentiation between
alpha- and beta- form of
anomeric carbon (based on
the OH group)