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Lipid Revision

Lipid Revision. 1. H H H H H H H H H H H O             H-C – C – C – C – C – C – C – C – C – C – C – C – OH            H H H H H H H H H H H.

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Lipid Revision

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  1. Lipid Revision 1

  2. H HHHHHHHHHH O             H-C – C – C – C – C – C – C – C – C – C – C – C – OH            H HHHHHHHHHH What is this structure Fatty Acid 2. What is it composed of ? Hydrocarbon and carboxyl group O  C –OH Carboxyl group Hydrocarbon 2 Fatty acids = Hydrocarbon + carboxyl group

  3. H HHHHHHHHHHHHHH O                 H – C – C – C – C – C – C – C – C – C – C – C – C – C - C – C – C – OH                H HHHHHHHHHHHHHH • Give a name for this fatty acid • Palmitic acid • What type of fatty acid is this? • Saturated • Draw the structure of oleic acid H HHHHHHHHHHHHHHHH O                   H – C – C – C – C – C – C – C – C – C = C – C – C – C – C – C – C – C – C – OH                H HHHHHHHHHHHHHH 3

  4. H HHHHHHHHHHHHHH O                 H – C – C – C – C – C – C – C – C – C – C – C – C – C - C – C – C – OH                H HHHHHHHHHHHHHH • Give another way how the above fatty acid can be written • CH3(CH2)14COOH H HHHHHHHHHHHHHHHH O                   H – C – C – C – C – C – C – C – C – C = C – C – C – C – C – C – C – C – C – OH                H HHHHHHHHHHHHHH • Give another way how the above fatty acid can be written • CH3(CH2)7CH=CH(CH2)7COOH 4

  5. O  RC – OH If the general formula for a fatty acid is, what is R equal to? - R = a hydrocarbon group H  H– C – OH  H– C – OH  H– C – OH  H What is this compound? Glycerol/trihydroxy alcohol Circle the hydroxyl group 5

  6. Form an ester linkage between the top C of glycerol and the fatty acid H O   H– C – O – C–R  H– C – OH  H– C – OH  H H  H– C – OH  H– C – OH  H– C – OH  H O  RC – OH What is the name of the product? Monoacyglycerol 6

  7. Form an ester linkage between the top C of glycerol and the fatty acid H  H– C –OH  H– C –OH  H– C –OH  H O ll - C-R H  H– C – OH  H– C – OH  H– C – OH  H O  RC – OH What is the name of the product? Monoacyglycerol 7

  8. Similarly, form ester linkages with the remaining C’s of glycerol and two more molecules of fatty acids H O   H– C – O – C–R O  H– C – O – C – R O  H– C – O – C – R  H What is the name of the product? Triacyglycerol You have just constructed a lipid!!!! 8

  9. O  C17H33C – OH Draw the structure of a lipid composed of and glycerol O  O – C – C17H33 H  H– C – O – H H– C – O – H H– C – O – H  H What is the name of this lipid? Tristearin O  O – C – C17H33 O  O – C – C17H33 9

  10.  A lipid is H O   H– C – O – C– C17H33 O  H– C – O – C – C17H33 O  H– C – O – C – C17H33  H Hydrocarbon Hydrocarbon Hydrocarbon 10

  11. PHOSPHOLIPIDS • What is another name for phospholipids? • Phosphoglycerides /Phosphoglycerol • What are the components of phospholipids? • Glycerol • 2 fatty acids • Phosphate • alcohol • Draw the structures of the components of phospholipids. H  H– C – OH  H– C – OH  H– C – OH  H O  – P – O-  O – OH O  RC – OH 11

  12. O  – C– R How do you draw the structure of a phospholipid? H  H– C – O – H H– C – O – H H– C – O – H  H O  – C– R O  – P – O-  O What is this compound? Phosphatidic Acid 12

  13. How do you form a phospholilpid? H  H– C – O – H H– C – O – H H– C – O – H  H O  – C– R O  – C– R - R O  – P – O-  O What is R? Glycerol or other alcohols Phosphoglyceride/Phospholipids/ phosphoglycerol • Phosphatidic Acid 13

  14. Glycerol @ other alcohols Phosphoglycerol = Phosphoglyceride 14

  15. SPHINGOLIPID • What is the main structure for sphingolipid? • Sphingosine • Draw the structure of sphingosine • Draw the structure of glycerol and compare between the two CHCH(CH2)12CH3  CHOH  CH NH2  CH2OH H2C OH  H2COH  H2C OH Sphingosine Glycerol 15

  16. SPHINGOLIPID • What are the functional groups in sphingosine? • Hydroxyl (OH) • Amino (NH2) • What do you get if you add fatty acid? • Ceramide which is a sphingolipid CHCH(CH2)12CH3  CH OH  CH NH2  CH2 OH O וּוּ C - R Fatty acid 16 CERAMIDE

  17. CHCH(CH2)12CH3 CHOH CHNH2 CH2 OH CHCH(CH2)12CH3 CHOH O ll CHNHCR CH2 OH SPHINGOSINE CERAMIDE 17

  18. CHCH(CH2)12CH3 CHOH O ll CHNHCR CH2 OH CHCH(CH2)12CH3 CHOH O ll CHNHCR O ll CH2 OPOCH2CH2N(CH3)3 Ι O CERAMIDE SPHINGOMYELIN 18

  19. Draw the basic ring structure of steroid nucleus • What is it called? • Perhydrocyclopentanophenanthrene 19

  20. What is the difference between steroid and sterol • A sterol has one or more OHgroups • Give an example of sterol • Cholesterol CH3 l CHCH2CH2CH2CHCH3 l CH3 CH3 Cholesterol (C27 H46O ) Sterol OH Steroid 20

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