Beruflich Dokumente
Kultur Dokumente
This version of the presentation does not have some graphics in the interest of making the file smaller
Fig 9-8
1
Reducing Sugars: Aldoses
6
HO
Fig 9-10
5
O
4
OH 1
2
HO 3 OH
OH
α-D-glucopyranose
2 Cu+2
OH-
Cu2O(s)
OH- 6
HO
5
O
4
OH 1
O
2
OH
Tartarate: Fehlings’s solution α-D-glucuronic acid lactone
Citrate: Benedict’s solution
O O
CH2OH
1
CH1 CH1
C O
2 H C OH HO C H
HO C H
2 2
2 Cu+2 Cu2O(s)
3
OH- HO C H
3 + HO C H
3
H C OH
4 H C OH H C OH
4 4
H C OH
5 H C OH H C OH
5 5
CH2OH
6 CH2OH CH2OH
6 6
2
Functions of Monosaccharides
Glyceraldehyde and dihydroxyacetone (C3):
-Intermediates in glycolysis
-Precursors for glycerol used for triglyceride and
phosphoglyceride biosynthesis
H O
C
NH2
O
-
N
O P O O
OH OH
O NH2
N
N
N N
-
O P O O
O
OH OH
**NAD
(oxidized form)
3
Functions of Monosaccharides
(CH2O)n partly oxidized, readily available energy source
Glucose (C6):
-Source of energy for plants and animals in glycolysis
-Monomer unit for cellulose in plants
Fructose (C6):
-Source of energy for plants and animals in glycolysis
DISACCHARIDES: Maltose
Provides energy for
maltose
HO
O
HO
O
germinating seeds
HO HO (breakdown product of
HO O OH amylopectin and amylose
OH OH
in germinating seeds)
O-α-D-glucopyranosyl-(1 -> 4)-α (or β)-D-glucopyranose
(ending = "ose" since anomeric OH is free)
4
DISACCHARIDES: Sucrose
sucrose Storage saccharide in…
HO
O
HO
glucose = α
HO …sugar beets
OH O
O
HO
fructose = β
HO OH
…sugar cane
OH
O-α-D-glucopyranosyl-(1 -> 2)-β-D-fructofuranoside
(ending = "oside" since anomeric O is derivatized)
Hydrolyzed into glucose and
fructose by an enzyme called
invertase
DISACCHARIDES: Lactose
lactose
HO
O OH
HO
HO
O O
HO OH
HO
OH
5
WRITING AMYLOSE POLYMER
HO HO
O O
HO HO
O
HO O OH
O
OH OH
THREE-DIMENSIONAL AMYLOSE
~ 20 D
~ 20 D
Fig 09-16.GIF
http://www.wellesley.edu/Chemistry/chem227/sugars/amylose-end.gif
6
BIOLOGICAL FUNCTION OF AMYLOSE
Amylose is a storage polymer for glucose in plants
HO HO
O O
HO HO
O O O
OH OH
7
HYDROLYSIS OF AMYLOSE: β-Amylase
(in germinating seeds, sweet potatoes)
β-Amylase is an exoglycosylase:
It removes maltose units from the nonreducing
ends of the amylose (> 4)
HO HO
O O
HO HO
HO
O O O
OH OH
8
Periodate oxidation (lab) and methylation
can determine degree of brancing
METHYLATION OF GLYCOGEN VERSUS AMYLOPECTIN
HO
O
OH branch point
O
O α (1 - 6)
OH
HO HO HO
O O O O
OH OH OH OH
HO O O O O O OH
OH OH α (1 - 4) OH OH
nonreducing end linkages reducing end
O
CH3I OR CH3OSOCH3
O
H+
HO
O
OH branch point
O
O α (1 - 6)
OH
HO HO HO
O O O O
OH OH OH OH
HO O O O O O OH
OH OH α (1 - 4) OH OH
nonreducing end O linkages reducing end
O
-
O P OH
-
O
9
Enzyme that hydrolyze amylopectin
Polymer Hydrolytic Enzymes
Amylopectin Starch Phosphorylase
gluc-(gluc)n + Pi (gluc)n + gluc-1-Pi
HO
O
OH branch point
O
O α (1 - 6)
OH
HO HO HO
O O O O
OH OH OH OH
HO O O O O O OH
OH OH α (1 - 4) OH OH
nonreducing end O linkages reducing end
O
-
O P OH
-
O
Fig 15-13.GIF
10
WRITING CELLULOSE STRUCTURE
HO
O O
HO
HO
O O
OH
HO
Actual O
orientation OH
Linear β-(1 ->4) linked polymer of glucose
of adjacent
glucose
residues:
Fig 9-17.GIF
Microfibrils aggregate
into stiff, rigid structures
11
What is the biological function of cellulose?
Cellulose provides…
1. Structural ridigity to plants
2. Another polymer for glucose
storage
12