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HEXOSE METABOLISM
AJI SUTRISNOFOOD SCIENCE AND TECHUNIVERSITAS BRAWIJAYA
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Common Hexoses
OCH2OH
HH
OHOH
H
H
OH
H
OH
OCH2OH
HOH
HOH
H
H
OH
H
OH
OCH2OH
HH
OHOH
H
OH
H
H
OH
O
OH
CH2OH
HH
OH H
CH2OH
OH
a-D-Glucose a-D-Galactose a-D-Mannose
a-D-Fructose
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Sources of Sugars
• Glucose: lactose (dairy products) and
sucrose (table sugar)• Fructose: fruits and sucrose• Galactose: lactose• Mannose: polysaccharides and glycoproteins
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Fructose Metabolism
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Sucrose(Table Sugar)
O--D-Glucopyranosyl-(1—> 2)--D-Fructofuranoside
OO
CH2OH
HHO
H
HO OH
H
H
OH
H HOCH2
H
OH H
H
CH2OHO
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All Tissues
Sucrose -D-glucose + -D-f ructosea-Glucosidase(I nvertase)
Glycolysis
Mutarotation-D-f ructose
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Cleavage of Sucrose(-glucosidase or invertase)
OO
CH2OH
HHO
H
HO OH
H
H
OH
H HOCH2
H
OH H
H
CH2OHO
H2O
OCH2OH
HH
HO OH
H
H
OH
H
OH
OHO
HOCH2
H
OH H
H
CH2OHH
Glucose Fructose
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Mutarotation of Fructose
HOCH2 OH
CH2OHH
OH
HO
H
OCH2OH
C
O
H OHCH2OH
CHO HCH OH
C HOCH2
H
CH2OH
OHH
OH
HO
H
O
D-Fructose-D-Fructose -D-Fructose
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Muscle Metabolism of Fructose
(Anaerobic Glycolysis)Large Amounts of Hexokinase
OHO
HOCH2
H
OH H
CH2OH
OHH
ATP ADPO
HOPOCH2
H
OH H
CH2OH
OHHHexokinase
-D-Fructose
Glycolysis
Fructose-6-P
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Liver Metabolism of Fructose I
(Little Hexokinase)
OHO
HOCH2
H
OH H
CH2OH
OHH
ATP ADPO
HOHOCH2
H
OH H
CH2OP
OHHFructokinase
-D-Fructose
(Committed Step)
Fructose-1-P
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Liver Metabolism of Fructose II
CH2OPCCCCCH2OH
OHHOOHH
H OH
Glycolysis
CHOCHOHCH2OH
Glyceraldehyde
OHO
HOCH2
H
OH H
CH2OP
OHH
DHAP
CH2OPCCH2OH
O
Fructose-1-P
Fructose-1-P Aldolase
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Mechanism of Aldolase(Formation of Schiff Base)
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Mechanism of Aldolase(Aldol Cleavage Reaction)
HH
H2COPCCCCCH2OH
NHHOOHOHH
Enzyme CH2OPCC
NHEnzymeHHO
:CHOCHOHCH2OH
:B
+
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Mechanism of Aldolase(Formation of Dihydroxyacetone-P)
CH2OPCC
NHHHO
Enzyme:
H2OCH2OPCCH2OH
O
H2N–Enzyme
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Liver Metabolism of Fructose III
CHO
CHOH
CH2OH
ATPADP
CHO
CHOH
CH2OP
NAD+
CH2OH
CHOH
CH2OH
NAD+
CH2OH
C
CH2OP
O
CH2OH
CHOH
CH2OP
Glyceraldehyde
Glyceraldehyde Kinase
Glyceraldehyde-3-P
Glycolysis
AlcoholDehydrogenase
NADH + H+
Glycerol
GlycerolKinase
Glycerol-3-P
Dihydroxyacetone-P(DHAP)
NADH + H+
Glycerol-PDehydrogenase
Triose-PIsomerase
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Complexity of Liver Metabolism
Breakdown of Many Metabolites
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Fructose Intolerance
• Too Much Fructose– Fructose-1-P Aldolase is rate-limiting– Depletion of Pi– Reduction in [ATP]– Increase in glycolysis– Accumulation of lactate (acid) in
blood• Fructose-1-P Aldolase
Deficiency (Genetic Disease)
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Galactose Metabolism
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Lactose Metabolism(Dairy Products)
Glycolysis
O
O
CH2OH
HHO
HOH
H
H
OH
H
O
CH2OH
H
OH
H
H
OH
H
OH
O
CH2OH
HHO
HOH
H
H
OH
OH
H
Lactose
Glucose
-D-Galactose
-Galactosidase
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Mutarotation of -D-Galactose
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Glycolytic Enzymes are specific and do not recognize
galactose!
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Need Epimerization
OCH2OH
HHO
H OH
H
H
OH
H
OH
OCH2OH
HH
HO OH
H
H
OH
H
OH
GlucoseGalactose
Epimerization
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Phosphorylation of Galactose
O
CH2OH
HOH
HOH
H
H
OH
H
OH
ATP ADPO
CH2OH
HOH
HOH
H
H
OH
H
OPO3=Galactokinase
Galactose Galactose-1-P
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Activation of Galactose
O
CH2OH
HOH
HOH
H
H
OH
H
OPO3=
O
CH2OH
HH
OHOH
H
H
OH
H
O P O
O
O–
P O
O–
O
Uridine
O
CH2OH
HOH
HOH
H
H
OH
H
O P O
O
O–
P O
O–
O
Uridine
UMP
Galactose-1-P
Galactose-1-PUridylyl Transferase
UDP-Glucose
Glucose-1-P
UDP-Galactose
Glucose-6-P
Phosphoglucomutase
Glycolysis
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Epimerization of UDP-Galactose
O
CH2OH
HOH
HOH
H
H
OH
H
O P UMP
O
O–
[NAD+]O
CH2OH
HH
OHOH
H
H
OH
H
O P UMP
O
O–
UDP-Galactose-4-Epimerase
UDP-GlucoseUDP-Galactose
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Mechanism of Epimerization
O
C
CH2OH
H
OH
H
H
OH
H
O P UMP
O
O–
O
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Why UDP-Galactose?
GlycoproteinsGlycolipids
(Require UDP-Galactose)
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Formation of Glucose-1-P
O
CH2OH
HH
OHOH
H
H
OH
H
O P UMP
O
O–
PPi UTPO
CH2OH
HH
OHOH
H
H
OH
H
O P O–
O
O–
UDP-GlucosePyrophosphorylase
UDP-Glucose Glucose-1-P
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Formation of Glucose-6-P
O
CH2OH
HH
OHOH
H
H
OH
H
O P O–
O
O–
O
CH2OPO32–
HH
OHOH
H
H
OH
H
OHPhosphoglucomutase
Glucose-6-PGlucose-1-P
Glucose-6-P ——> Glycolysis
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Galactosemia(Mental Retardation and Death)
TreatmentGalactose-free diet
(reversal of all symptoms except mental retardation)
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Cataracts
CCC
OHH
OH
HHOC HHOC OHHCH2OH
CH2OHCC
OHHHHO
C HHOC OHHCH2OH
NAD(P)H NAD(P)+
Galactose Galactitol
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Mannose Metabolism
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Phosphorylation of Mannose
OCH2OH
HH
OHOH
H
HO
H
H
OH
ATP ADPO
CH2OP
HH
OHOH
H
HO
H
H
OH
-D-Mannose
Hexokinase
Mannose-6-P
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Isomerization of Mannose-6-P
OCH2OP
HH
OHOH
H
HO
H
H
OH
O
HO
POCH2
HH
OH H
CH2OH
OHPhosphomannoseIsomerase
Fructose-6-PMannose-6-P
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THANK YOU
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Mechanism of Isomerization
H C
CH O
O H
R
Aldose
C
CH O
O H
R
BH + C
CH O
O
R
BH
H
H C
H
O
C O
R
H
Ketose
B:B: +
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Aldoses and Ketoses
CC
OH
COHHHHO
CC
OHH
CH2OHOHH
CH2OHCCCCCH2OH
OHHOOHHOHH
D-glucose D-f ructose
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Mutarotation of Glucose
HH
HOO
HC
O
C
CH2OH
OH
OH H
OH
HO
OCH2OH
OH
OH
OR
OHHO
OCH 2OH
OH
OH
C
H
HO H
OH
CO
H OH
CH2OH
C
CH OH
CH ....
or
+
[+18.7°][+112.2°]
anomericcarbonatom
-D-glucose-D-glucose
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Mutarotation of Fructose
HOCH2 OH
CH2OH
OH
HO
OCH2OH
CH OHCH2OH
CHO HCH OH
C OHOCH2 CH2OH
OH
OH
HO
O
D-Fructose -D-Fructose-D-Fructose