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LIPIDS (Diverse class of compounds defined by their insolubility in water) A. Fatty Acids B. Neutral Fats (Triglycerides) C. Steroids D. Phospholipids E. Micelles F. The phospholipid Bilayer

Dr. Ross Feldberg Tufts University, Medford, MA (near Boston) Questions on the lectures? Send them to class e-mail so everyone can see the answers

The Building Blocks: Isoprene and the Fatty Acids

Charged at one end, but long nonpolar tail.... it this hydrophobic or hydrophilic?

CH3CH2CH2CH2CH2CH2CH2CH2CH2COOH CH3(CH2)8COOH

Fatty Acids
(LONG HYDROCARBON CHAIN WITH CARBOXYLIC ACID AT ONE END)

CH2-CH2-(CH2)13-CH2-CH2-COOH stearic acid C18 saturated (No double bonds)

CH2-CH2-(CH2)5-CH2-CH=CH-CH2-(CH2)5-CH2-COOH oleic acid C18 1 cis double bond A cis double bond introduces a kink in the molecule - a bend in its structure This is an unsaturated fatty acid

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Neutral Fats form when the carboxyl groups of three fatty acids condense with the hydroxyl groups of glycerol.
Q. What do we call the functional group that is formed?

what does this zigzag line represent?

Neutral fats are your major long-term energy reservoir (stored in adipocytes a specialized fat storage cell that makes up fat tissue)

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Neutral Fats consist of three fatty acids linked to glycerol. This is the storage form that excess calories take in your adipose tissue.

Saturated fatty acids have no double bonds and neutral fats with no double bonds form solids (grease) found in animals Unsaturated fatty acids with cis double bonds disrupt the compact structure and neutral fats with such fatty acids form liquid structures (oils) - found in plants)

Water Structure and solvent properties H + O H -

Water is a dipole, making it a good solvent for charged or polar solutes

Electronegativity

-C=O +

-N-H + -

-C-H
no in charge across bond

In biological systems, oxygen, nitrogen and sulfur have high electron affinity. When they form bonds to C or H the covalent bond tends to have an unequal charge across it (POLAR COVALENT BONDS) In contrast, Bonds between C and H are NONPOLAR Molecules that are made up mainly of Carbons and Hydrogens tend to be HYDROPHOBIC - they associate with one another when placed in water rather than with the water molecules. They are insoluble in water.

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Unsaturated cis fats form oils (olive oil, canola oil)

Saturated fats and trans fats tend to form tightly packed solids (margarine)

Fats with cis double bonds can not pack together to form solids
http://scholar.hw.ac.uk/site/chemistry/activity3.asp

Fats with trans double bonds also show close packing - these are synthetic and used in baking, but now thought to be unhealthy
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Fused isoprene units make up a steroid (a 4membered ring system)


CH3

STEROIDS
H3 C CH3 CH3

CH3

Cholesterol

Q. What does this indicate? Steroids have a four-membered fused ring system

HO

Testosterone

PHOSPHOLIPIDS GLYCEROL ESTERIFIED TO TWO FATTY ACIDS AND A PHOSPHORIC ACID


O H C O C CH2CH2 CH2 CH2 CH2 CH2 CH2 CH2CH3 O H C O C CH CH CH CH CH CHCH CH CH CH 2 2 2 2 2 2 2 3 H

Hydrophobic tail groups

O R O P O CH2 O-

charged head group

Where R = glycine, serine, ethanolamine, choline or a variety of other small molecules

The cell membrane is made up of a phospholipid bilayer

Phospholipids associate to form micelles or lipid bilayers

soaps form these!


(animal fat + lye to give CH3(CH2)nCOO- Na+) insoluble fats will be trapped in the center of the micelles

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ARTIFICIAL MEMBRANES:

1. LIPOSOMES

Lipid Bilayers can also form small droplets called liposomes in which there is an aqueous interior. These fuse with cell membranes and can be used to carry into cells hydrophilic molecules that would not normally cross the membrane.

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Doxorubicin: An anticancer agent used in treatment of metastatic breast cancer and delivered to cells by being packaged in liposomes

Q. What is the most fundamental characteristic of a cell ?

Phospholipid bilayers are Selectively Permeable

These require protein carriers to get them across the membrane

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In diffusion 1. The net movement of molecules is always down its concentration gradient 2. Since this is a spontaneous process, it is possible to capture some of the energy decrease in moving to equilibrium as work 3. The rate of diffusion is proportional to the concentration difference, the temperature and the size of the molecules (Einstein was the first to derive an accurate equation for diffusion!)

Osmosis is the diffusion of water that takes place when a membrane impermeable solute is present at different concentrations on either side of a membrane

Molecules in compartment 2 can NOT cross the membrane

We actually measure this by determining how much pressure would have to be exerted on compartment 2 to keep its volume constant = Osmotic Pressure 1 2

Osmosis: The diffusion of water down its concentration gradient


high salt solution water balanced salt solution

During profound dehydration, you need to rehydrate with a balanced salt solution, not water

In addition to the membrane that defines a cells outer boundary (the plasma membrane), in eukaryotic cells there are a number of membrane bounded internal compartments.

The various cell membranes have different lipid components and different proteins that determine the structure and function of that membrane.

What are some of the properties of biological membranes? 1. Are they rigid or fluid? 2. What is the position of membrane proteins in the membrane? 3. How do polar and charged molecules get across the membrane? 4. What roles do membrane proteins and carbohydrates play?

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Mouse Membrane Protein

Human Cell

Human Membrane Protein

Fuse the two cell types

Mouse Cell

Hybrid cell T=0

Hybrid Cell T = 60 min

Use specific fluorescent antibodies to identify mouse-specific and human -specific membrane proteins Q. What might you conclude from this experiment?
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The Fluid Mosaic Model of the Cell Membrane

Cholesterol

1.

The lipid bilayer (fatty acids and groups attached to phosphate vary from membrane to membrane) Saturated Fatty Acids & Cholesterol (animal membranes) both reduce fluidity

2.

The Fluid Mosaic Model of the Cell Membrane

1.

Proteins: Peripheral (easy to remove) and Integral (requires dissolving membrane to remove) Carbohydrates bound to proteins (glycoproteins) and to lipids on exterior surface. The different blood groups (A, B and O) reflect different sugars on the cell surface of blood cells

2.