Download Macromolecules

Macromolecules
•  Monomers and Polymers
• 
• 
• 
• 
• 
• 
• 
–  Dehydration synthesis
•  Carbohydrates
–  Sugars and starches
•  Lipids
–  Fats and oils
–  Phospholipids
–  How soap works
R-OH
R-SH
R-C=O
R-COOH
R-NH2
R-PO4
R-CH3
hydroxyl
sulfhydryl
carbonyl
carboxyl
amino
phosphate
methyl
7 Sept. 2012
Each has a
balance point
Ionizable Functional Groups
Carboxylic acid
Ionizable Functional Groups
Amine
Carboxylic acid
R-CH2N-H
R-COOH
pKa
3 to 5
H+
pKa
H
Most
organic
Acids
Most
organic
Acids
3-to-5
8 to 11
H
+
R-CH2N-H
R-CH2N-H
R-COOH
pKb
H
Most
organic
Acids
R-COO-
HOH
Amine
R-COO-
-OH
H
H+
H
+
R-CH2N-H
HOH
pKb
Most
organic
Acids
8-to-11
-OH
H
At normal pH these are charged ions
Isomers are molecules with the same
H
H
molecular formula but different structures and
H H H H H
properties
(a) Structural isomers
–  Structural
H
C
C
C
C
C
H
H
H
H
H
C
–  Geometric
H
H
X
CO2H
H
H
H
C
C
C
H
H
H
C
C
H
X
Carvone
Caroway
Spearmint
H
Ibuprofen
C
NH2
CH3
Isomers can have very different effects
H
CO2H
C
(c) Enantiomers
–  Enantiomers
H
C
H
C
H
H
X
X
(b) Geometric isomers
C
H
H
NH2
CH3
Figure 4.7 A-C
1
Figure 5.2
1
Macromolecules
• 
• 
• 
• 
2
3
Unlinked monomer
Dehydration
Synthesis
make by
taking water
away
Carbohydrates
Lipids
Proteins
Nucleic Acids
1
2
3
4
1
2
3
4
Longer polymer
Hydrolysis
Split by water
2
1
Simple sugars can be coupled together by
Dehydration Synthesis
= Maltose
O
H
OH H
H
H
H
OH
HO
OH
O
H
OH
H
H
OH
CH2OH
H
OHOH
H
HO
O
H
OH H
CH2OH
H
1– 4
1 glycosidic
linkage
H
4
O
H
OH H
H
H
OH
OH
H 2O
Glucose
CH2OH
H
O
H
OH
H
HO
Glucose + Fructose
H
CH2OH
H
OH
HO
O
H
H
H
HO
CH2OH
OH
OH
Maltose
H
H
OH
O
H
H
1–2
1 glycosidic
linkage
H
O
HO
CH2OH
O
2
H
Glucose
Fructose
C
C
OH
H
H
C
OH
H
C
OH
HO
C
H
C
OH
H
C
C
OH
H
C
OH
H
C
OH
H
H
H
H
H
H
Sucrose
H
H
C
OH
H
HO
C
H
OH
HO
C
H
C
OH
C
OH
H
H
Glucose
Galactose
H
C OH
C
O
H
H
C OH
HO
H
H
C OH
H
C OH
H
H
H
Dihydroxyacetone
H
Ribulose
Figure 5.3
C OH
C
O
C OH
Figure 5.5
5 and 6 Carbon Sugars CIRCULARIZE in Water
To FORM RINGS
OH
H
H
C OH
C
OH H
OH
C
H
C
O
H
OH
H
CH2OH
O
C
C
H
HO
Hexose sugars
(C6H12O6)
H
H
Glyceraldehyde
H 2O
= Sucrose
O
H
Ribose
CH2OH
Ketoses
Glucose
Pentose sugars
(C5H10O5)
C
OH
O
H
O
H
Aldoses
H
Glucose + GlucoseHO
Monosaccharides vary in Length and
Geometry
Triose sugars
(C3H6O3)
CH2OH
CH2OH
3
O
C H
C OH
C OH
C OH
H
Fructose
Cellulose
10 !m
0.5 !m
Cellulose
molecules!
!  Glucose
monomer!
Fig. 5-8
2
Fig. 5-7bc
Fats or triglycerides
(glycerol + 3 fatty acids)
Glycerol
+ Fatty acid
H
H
C
O
H
C
OH
HO
H
H
C
OH
C
OH
H
O
H
C
O
C
H
C
H
O
Fat molecule
H
C
O
C
H
C
H
O
H
C
H
OILS
WHY?
Solid
Saturated
O
O–
+
N(CH )
3 3
Choline
Phosphate
O
CH2
CH
O
O
C
O C
CH2
Glycerol
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
C
H
H
H
C
H
H
How will
phospholipids
behave in water?
O
Hydrophobic tails
Hydrophilic head
CH2
H
Phospholipid Bilayer
–  Glycerol + 2 fatty acids + phosphate
CH2
H
Like
Fig 5-12
•  Phospholipids
O
P
H
C
What are trans fats?
Liquid
Unsaturated or
Polyunsaturated
H
hydrophilic or hydrophobic?
Figure 5.11
FATS
O
H
C
Dehydration reaction
H
H
C
Fatty acids
Hydrophilic “head”
Hydrophobic
“tails”
Form
Boundaries
(a) Structural formula
3