chem 109 c bioorganic compounds - department of chemistry
TRANSCRIPT
Fall 2019HFH1104
Armen ZakarianOffice: Chemistry Bldn 2217
Chem 109 CBioorganic Compounds
http://labs.chem.ucsb.edu/~zakariangroup/courses.html
CLAS Instructor: Dhillon [email protected]
Chapter 25: Lipids
o Lipids are naturally occurring organic compounds that are not soluble in water, but soluble in non-polar solvents
Compounds containing fatty acids
o Waxes: (beewax, leaf and feather coatings etc.)
o Animal and plant triglycerides (oils and fats)
o Phospholipids: components of cell membranes
O
O
o Esters of fatty acids and glycerol are triglycerides [components of fats and oils]
Chapter 25
o Solid triglycerides [fats] have mostly saturated carbon chainso Liquid triglycerides [oils], higher content of unsaturated carbon chains
Chapter 25
Problem 3. Draw a structure of an optically inactive fat that, when hydrolyzed, gives glycerol, one equivalent of lauric acid, and two equivalents of stearic acid.
o Converting oils to fats found in margarine and shortening
Chapter 25
O
O
O
O
OO
“trans fat”
O
O
O
O
OO
oil
O
O
O
O
OO
margarine/shortening
H2Pd/C
o Sodium or potassium salts of fatty acids are soaps
Chapter 25: Soaps
o Sodium or potassium salts of fatty acids are soapso Soaps form micelles in water, which trap non-polar
contaminants
Chapter 25: Soaps
o Detergents are [potassium] salts of benzenesulfonic acids
Chapter 25: Soaps
o Phospholipids: cell membranes and lipid bilayers
Chapter 25: Phospholipids
o Phospholipids: cell membranes and lipid bilayers
Chapter 25: Phospholipids
o Phosphoglycerides: derived from glycerol
Chapter 25: Phospholipids
O
O
O
O
OPRO O
O
R = CH2CH2NH3+
phosphatidylethanolamine
R = CH2CH2NMe3+
phosphatidylcholine
R = CO2
NH3+
phosphatidylserine
o Sphingolipids: cell membranes in the brain
Chapter 25: Phospholipids
NH2HO
OH sphingosine
both stereocenters have S configuration
o Sphingolipids: cell membranes in the brain
Chapter 25: Phospholipids
NH2HO
OH sphingosine
both stereocenters have S configuration
NHHO
O ROP
O
O
O+H3N
NHHO
O ROP
O
O
O+Me3N
with phosphoethanolamine
with phosphocholine
sphingomyelins