Transcript No Slide Title

Carbohydrates
glucose
C6H12O6
[C.H2O]6
H3O+ not hydrolyzed
glucose
into smaller sugars
monosaccharide
lactose
+
H3O
disaccharide
1 glucose + 1 galactose
+
H3O 1 glucose + 1 fructose
raffinose
+
1 galactose
trisaccharide
starch, cellulose
polysaccharide
O
H
C
H C OH
H C OH
H C OH
CH2OH
ribose
polyhydroxyaldehyde
aldopentose
CH2OH
C O
HO C H
H C OH
H C OH
CH2OH
fructose
polyhydroxyketone
ketohexose
O
CH
H
OH
CH2OH
D-(+)-glyceraldehyde
O
CH
HO
H
CH2OH
L-(-)-glyceraldehyde
O
C H
HO
H
H
OH
H
OH
CH2OH
D-(-)-arabinose
L-(+)-arabinose
O
C H
HO
H
H
OH
H
OH
CH2OH
D-(-)-arabinose
O
C H
H
OH
HO
H
HO
H
CH2OH
L-(+)-arabinose
O
C H
HO
H
H
OH
H
OH
CH2OH
D-(-)-arabinose
OH
O
CH2OH
OH
OH
-D-arabinose
a furanose
H
HO
HO
H
O
C H
OH
H
H
OH
CH2OH
D-galatose
CH2OH
O OH
HO
-D-galactose
OH
OH
+
CH2OH
O
HO
anomers
OH
-D-galactose
OH
OH
CH2OH
HO
H
OH
OH
OH
HO
O
CH2OH
OH
H
OH
O
OH
HO OH
O
HO
HO
OH
-D-galactopyranose
O
pyran
-D-galactose [] = 150.7°
-D-galactose [] = 52.8°
mutarotation
[] = 80.2˚
OH-
O
HO
OH
O
HO
OH
OH-
O
HO
OH
O
HO
H
O-
O-
O
HO
H
O-
HO
H
O
OHO
OH
O
HO
O
H
OHO
O
O
H
HO
O-
OHO
O
O
H
O-
HO
O
HO
OH
HO OH
OH
HO
O
HO
HO
CH3OH
HO
+
H
OH
O
HO
OCH3
methyl- -D-galactopyranoside
a glycoside
Disaccharides
Lactose
OH
HO
OH
O
HO
OH
OH
D-galactose
HO
HO
O
OH
D-glucose
OH
OH
HO
OH
O
HO
OH
O
HO
O
OH
OH
-1,4-glycosidic linkage
undergoes mutarotation
OH
HO
HO
O
OH O
HO
HO
O
HO
an -glycosidic linkage
OH
Oxidations of Sugars
OH
HO
HO
H
HO
H
H
O
HO
OH
O
C H
OH
H
OH
OH
CH2OH
[Ox]
H
HO
H
H
O
COOH
H
OH
OH
CH2OH
oxidizing agents: Ag(NH3)2+,
2+
Cu /OH
sugars that react with these oxidizing
agents are called reducing sugars
these monoacids are called aldonic
acids
OH
HO
HO
+
O
HO
Ag(NH3)2
OCH3
a nonreducing sugar
NR
Glycolysis
CHO
OH
HO
OH
OH
CH2OPO3H2
Glycolysis
CHOH
CHO
COH
OH
HO
HO
OH
OH
OH
OH
CH2OPO3H2
CH2OPO3H2
Glycolysis
CHOH
COH
HO
OH
OH
CH2OPO3H2
Glycolysis
CHOH
CH2OH
COH
C O
HO
HO
OH
OH
OH
OH
CH2OPO3H2
CH2OPO3H2
Glycolysis
CH2OPO3H2
CH2OPO3H2
C O
C O
CH2OH
HO
OH
OH
CH2OPO3H2
HC O
OH
CH2OPO3H2
Glycolysis
CH2OPO3H2
C O
CH2OH
HC O
OH
CH2OPO3H2
Reduction of the carbonyl group
Alditol formation
OH
O
HO
HO
HO
OH
H
Br2/H2O
HO-Br
OH
HO
HO
Br
O
O
HO
H
OH
Br
O
O
HO
HO
HO
H
OH
HO
HO
O
HO
O
OH
O
HO
HO
Br
O
OH
H
OH
HO
HO
O
OH O
O
HOCH2(CH)nCH
OH
HNO3
H2O
O
O
HOC(CH)nCOH
OH
an aldaric acid
IO4- oxidation
O
H
H
OH
+ HIO4
OH
+ HIO3
O
C O
+ HIO4
H
OH
HO
O
+ HIO3
O
HOH2C O CH2OH
CH2OH
C O
H
OH
H
OH
H
OH
CH2OH
OCH3
HIO4
OH OH
O CH OH
2
HO
OCH3
OH OH
HIO4
HOH2C O CH2OH
OCH3
OH OH
HOH2C O CH2OH
HIO4
O
H
H
OCH3
O
O CH OH
2
HO
OCH3
OH OH
HIO4
O
O CH OH
2
H
H
OCH3
O
O
HCOH
Fischer-Kiliani Synthesis
CN
CN
O
H
HO
OH
H
C H
OH
H
OH
H
OH
H
HCN
+
H
HO
H
HO
H
HO
OH
H
OH
H
OH
H
CH2OH
CH2OH
CH2OH
H
H
HO
H
CN
CN
HO
H
OH
OH
OH + H
HO
H
H
H
OH
OH
CH2OH
CH2OH
H2/H2O
Pd
BaSO 4
H
H
HO
H
O
CH
OH
OH
+
H
OH
CH2OH
O
CH
HO
H
HO
H
epimers
H
OH
H
OH
CH2OH