Carbohydrates Flashcards
carbohydrates roles
energy storage/ transport (metabolic energy)
cell-cell communication/ adhesion
host-pathogen/symbiont interactions
structural components
DNA/RNA components
carbohydrates elemental composition
C,H,O,S/N
2+ hydroxyl groups
2 simplest carbs
glyceraldehyde
dihydroxyacetone
aldose number of asymmetric carbons
aldoses have 1 more asymmetric carbons than ketoses
chiral centre
4 different groups
different 3D conformation
C1
aldehyde carbon
C2
carbonyl group in ketoses
aldehyde + alcohol
hemiacetal
pyranose
6C ring due to similarity to pyran
why do aldose sugar rings form
alcohol is part of same molecule as aldehyde/ ketone
aldose sugar rings in solution
dominate as more energetically favorable than open-chain form
ketone + alcohol
hemiketal
non-planar chair configurations
axial (opposite directions on adjacent carbons)
equatorial (less crowded)
anomers
sugar isomers with 2 anomeric carbons
additional chiral crabon for ring-formation aldoses
C1
alpha anomer
C1/C5 have same stereochemistry
beta anomer
C1/C5 have different stereochemistry
anomeric C in ketones
C2
glucose assymetric carbons and variations
2 stereoisomers D/lL
4 asymmetric carbons
what form is glucose most commonly found in?
D form
dextrorotatory
rotate plane of polarised light to the right
laevorotatory
rotate plane of polarised light to left
epimers
when only asymmetric C2,3 or 4 are in a different configuration to glucose
cylization of open-chain form of glucose
C5 hydroxyl group attacks oxygen atom of C1 aldehyde group to form intramolecular hemiacetal
2 anomers alpha/ beta
ketohexose cyclization
C2 keto group reacts w C6/5 hydroxyl group to form intramolecular hemiketal
glycosidic bond
bond formation between hemiacetal group of sugar and oxygen of hydroxyl group via loss of water in condensation reaction
1-4, glycosidic linkage