1. Lipid Revision 1 1

2. Hydrocarbon 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 O  C –OH Fatty acids = Hydrocarbon + carboxyl group 1.What is this structure Fatty Acid 2.What is it composed of ? Hydrocarbon and carboxyl group Carboxyl group 2 2

3. H H H H 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 – C - C – C – C – OH                H H H H H H H H H H H H H H H 1.Give a name for this fatty acid Palmitic acid 2.What type of fatty acid is this? Saturated 3.Draw the structure of oleic acid H H H H H H 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 – C – C – C – C – C – C – OH                H H H H H H H H H H H H H H H 3 3

4. H H H H 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 – C - C – C – C – OH                H H H H H H H H H H H H H H H 1.Give another way how the above fatty acid can be written CH 3 (CH 2 ) 14 COOH H H H H H H 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 – C – C – C – C – C – C – OH                H H H H H H H H H H H H H H H 1.Give another way how the above fatty acid can be written CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 COOH 4 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 1.What is this compound? Glycerol/trihydroxy alcohol 2.Circle the hydroxyl group 5 5

6. H  H– C – OH  H– C – OH  H– C – OH  H O  R  C – OH 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 What is the name of the product? Monoacyglycerol 6 6

7. H  H– C – OH  H– C – OH  H– C – OH  H O  R  C – OH 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 What is the name of the product? Monoacyglycerol O ll - C-R 7 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 8

9. H  H– C – O – H H– C – O – H H– C – O – H  H O  O – C – C 17 H 33 O  O – C – C 17 H 33 Draw the structure of a lipid composed of and glycerol O  C 17 H 33  C – OH O  O – C – C 17 H 33 What is the name of this lipid? Tristearin 9 9

10.  A lipid is H O   H– C – O – C – C 17 H 33 O  H– C – O – C – C 17 H 33 O  H– C – O – C – C 17 H 33  H Hydrocarbon 10

11. PHOSPHOLIPIDS 1.What is another name for phospholipids? Phosphoglycerides /Phosphoglycerol 2.What are the components of phospholipids? a.Glycerol b.2 fatty acids c.Phosphate d.alcohol 3.Draw the structures of the components of phospholipids. H  H– C – OH  H– C – OH  H– C – OH  H O  R  C – OH O  – P – O -  O – OH 11

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

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

14. 14 Phosphoglycerol = Phosphoglyceride Glycerol @ other alcohols 14

15. 15 CH  CH(CH 2 ) 12 CH 3  CHOH  CH NH 2  CH 2 OH H 2 C  OH  H 2 C  OH  H 2 C  OH Sphingosine Glycerol SPHINGOLIPID 1.What is the main structure for sphingolipid? Sphingosine 2.Draw the structure of sphingosine 3.Draw the structure of glycerol and compare between the two 15

16. O וּוּ C - R CH  CH(CH 2 ) 12 CH 3  CH OH  CH NH 2  CH 2 OH SPHINGOLIPID 1.What are the functional groups in sphingosine? a.Hydroxyl (OH) b.Amino (NH 2 ) 2.What do you get if you add fatty acid? Ceramide which is a sphingolipid Fatty acid CERAMIDE 16

17. CH  CH(CH 2 ) 12 CH 3 CHOH CHNH 2 CH 2 OH CH  CH(CH 2 ) 12 CH 3 CHOH O ll CHNHCR CH 2 OH SPHINGOSINECERAMIDE 17

18. CH  CH(CH 2 ) 12 CH 3 CHOH O ll CHNHCR CH 2 OH CH  CH(CH 2 ) 12 CH 3 CHOH O ll CHNHCR O ll CH 2 OPOCH 2 CH 2 N(CH 3 ) 3 Ι O CERAMIDE SPHINGOMYELIN 18

19. 1.Draw the basic ring structure of steroid nucleus 2.What is it called? Perhydrocyclopentanophenanthrene 19

20. 1.What is the difference between steroid and sterol A sterol has one or more OH groups 2.Give an example of sterol Cholesterol OH CH 3 l CHCH 2 CH 2 CH 2 CHCH 3 l CH 3 Steroid Sterol Cholesterol (C 27 H 46 O ) 20

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