AP Biology

Lipids
energy storage

AP2006-2007
Biology
  Lipids are composed of C, H, O
 long hydrocarbon chain
 Diverse group
 fats
 phospholipids
 steroids
 Do not form polymers
 big molecules made of smaller subunits
 not a continuing chain

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  Structure:
 glycerol (3C alcohol) + fatty acid
 fatty acid =
long HC “tail” with COOH group at “head”

enzyme

dehydration synthesis
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  Triacylglycerol
 3 fatty acids linked to glycerol
 ester linkage = between OH & COOH

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 dehydration synthesis

enzyme

enzyme

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 Why do humans
like fatty foods?
 Long HC chain
 polar or non-polar?
 hydrophilic or hydrophobic?
 Function:
 energy storage
 very rich
 2x carbohydrates
 cushion organs
 insulates body
 think whale blubber!

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  All C bonded to H
 No C=C double bonds
 long, straight chain
 most animal fats
 solid at room temp.
 contributes to
cardiovascular disease
(atherosclerosis)
= plaque deposits

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  C=C double bonds in
the fatty acids
 plant & fish fats
 vegetable oils
 liquid at room temperature
 the kinks made by double
bonded C prevent the
molecules from packing
tightly together

mono-unsaturated?
poly-unsaturated?
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 saturated unsaturated

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  Lipids with fatty acids
Waxes
Fats and oils (trigycerides)
Phospholipids
Sphingolipids

 Lipids without fatty acids

Steroids

AP Biology 11
  Long-chain carboxylic acids
 Insoluble in water
 Typically 12-18 carbon atoms (even number)
 Some contain double bonds

corn oil contains 86%

unsaturated fatty acids and
14% saturated fatty acids

AP Biology 12
 Saturated = C–C bonds
Unsaturated = one or more C=C bonds

AP Biology 13
 Saturated fatty acids
 Fit closely in regular pattern

Unsaturated fatty acids

 Cis double bonds

 Kinks

AP Biology 14
  Contain only single C–C bonds
 Closely packed
 Strong attractions between chains
 High melting points
 Solids at room temperature

AP Biology 15
  Contain one or more double C=C bonds
 Nonlinear chains do not allow molecules
to pack closely
 Few interactions between chains
 Low melting points
 Liquids at room temperature

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 Double bonds in fatty O

 a C
acids usually have the 3 1 O
4
cis configuration. 2

Most naturally occurring

fatty acids have an fatty acid with a cis-D9
even number of double bond
carbon atoms.

Some fatty acids and their common names:

14:0 myristic acid; 16:0 palmitic acid; 18:0 stearic
acid; 18:1 cisD9 oleic acid
18:2 cisD9,12 linoleic acid
18:3 cisD9,12,15 a-linonenic acid
20:4 cisD5,8,11,14 arachidonic acid
20:5
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cisD 5,8,11,14,17 eicosapentaenoic acid (an omega-3)
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 Formed from glycerol and fatty acids

O
CH2 OH HO C (CH2)14CH3
O
CH OH + HO C (CH2)14CH3
O
CH2 OH HO C (CH2)14CH3
glycerol palmitic acid (a fatty acid)
AP Biology 19
 Esters of glycerol and fatty acids

ester bonds
O
CH2 O C (CH2)14CH3 + H2O
O
CH O C (CH2)14CH3 + H 2O
O
CH2 O C (CH2)14CH3 + H 2O

AP Biology 20
  Hydrolysis with a strong base
 Triglycerides split into glycerol and the salts
of fatty acids
 The salts of fatty acids are “soaps”
 KOH gives softer soaps

AP Biology 21
 O
CH2 O C (CH2)16CH3
O
CH O C (CH2)16CH3 + 3 NaOH
O
CH2 O C (CH2)16CH3
CH2 OH O
+-
CH OH + 3 Na O C (CH2)14CH3
salts of fatty acids (soaps)
CH2 OH

AP Biology 22
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  Structure:
 glycerol + 2 fatty acids + PO4
 PO4 negatively charged

It’s just like a

penguin…
A head at one end
& a tail
at the other!

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  Hydrophobic or hydrophilic?
 fatty acid tails = hydrophobic
 PO4 = hydrophilic head
 dual “personality”

It likes water
& also pushes
it away!

interaction with H2O

is complex & very
important!
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  Hydrophilic heads attracted to H2O
 Hydrophobic tails “hide” from H2O
 can self-assemble into “bubbles”
 bubble = “micelle”
 can also form bilayer
 early evolutionary stage of cell?

bilayer

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  Phospholipids create a barrier in water
 define outside vs. inside
 cell membranes

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  Phospholipids of cell membrane
 double layer = bilayer
 hydrophilic heads on outside
 in contact with aqueous solution outside of cell
and inside of cell
 hydrophobic tails on inside
 form core
 forms barrier between cell &
external environment

Tell them
about soap!

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 cholesterol,sex hormones
4 fused C rings
 different steroids created by attaching different
functional groups to rings

cholesterol 21
22
H3C CH3
18
H3C 20
12
CH3
19 17 16
H3C 11 13
14 15
10
1 9
2 8
3 6 7
AP Biology 4
HO 5
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  Important cell component
 animal cell membranes
 precursor of all other steroids
 including vertebrate sex hormones
 high levels in blood may contribute to
cardiovascular disease

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 Important component of cell membrane

helps keep
cell membranes
fluid & flexible

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  What a big difference a few atoms can make!

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 21
22
H3C CH3
18
H3C 20
12
CH3
19 17 16
H3C 11 13
14 15
10
1 9
2 8
3 6 7
4
HO 5

AP Biology
 Let’s build some
Lipids!

AP2006-2007
Biology