chemistry 8.2-carbohydrates-oligo-and-polysaccharides
TRANSCRIPT
Chapter 8 (part2)
Carbohydrates: oligo- and polysaccharides
Glycosidic Linkage
O
CH2OH
OH
OH
OHOH
O
CH2OH
OH
OH
OH
OH
H2OH2O
O
CH2OH
OH
OH
OHO
O
CH2OH
OH
OHOH
alcohol
hemiacetal
glycosidic linkage
Hydrolysis
Condensation
acetal
DisaccharidesO
CH2OH
OH
OH
OHO
O
CH2OH
OH
OH
OHH
H
H
H
H
H
H H
O
CH2OH
OH
OH
OH
O
O
CH2OH
OH
OH
OH
H
H
H
H
H
H
H
H
O
CH2OH
OH
OH
H
O
O
CH2OH
OH
OH
OH
H
OH
H
H
H
H
H
H
maltose cellobiose
lactose
sucrose
-D-glucosyl-(1->4)--D-glucopyranose)
-D-glucosyl-(1->4)--D-glucopyranose)
-D-galactosyl-(1->4)--D-glucopyranose)
-D-glucosyl-(1->2)--D-fructofuranose)
O
CH2OH
OH
OH
OH
H
H
H
H
OCH2OH
H
H
OH
OH
H
O
CH2OH
Higher Oligosaccharides
Oligosaccharide groups are incorporated in to many drug
structures
Polysaccharides
Amylose and Amylopectin
Iodine binding to starch
glycogen
Dextrans
Cellulose
Cellulose vs Amylose
Glucose units rotated 180o relative to next residue
cellulose
amylose
Cellulose
Chitin
Chitin vs Cellulose
Glycoproteins
O-linked Glycoproteins
Blood ABO Antigens
Structure of the ABO blood group carbohydrates,
R represents the linkage to protein in the secreted forms, sphingolipid in the cell-surface
bound formopen square = GlcNAc, open diamond = galactose, filled
square = fucose, filled diamond = GalNAc, filled diamond = sialic
acid (NANA)
N-linked Glycoproteins