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Lipid structure, function and chemistry

Lipid structure, function and chemistry. Lecture 18. Biological Lipids: Chemically and Functionally Diverse . Soluble in nonpolar solvents Hydrocarbon moieties Varied roles Storage of energy — “fat” Membranes Pigments Hydrophobic carriers Biological signals. Fatty Acids. Fatty Acids.

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Lipid structure, function and chemistry

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  1. Lipid structure, function and chemistry Lecture 18

  2. Biological Lipids: Chemically and Functionally Diverse • Soluble in nonpolar solvents • Hydrocarbon moieties • Varied roles • Storage of energy — “fat” • Membranes • Pigments • Hydrophobic carriers • Biological signals

  3. Fatty Acids

  4. Fatty Acids (saturated) (unsaturated)

  5. Some Common Fatty Acids

  6. Glycerides • Fatty acid esters of glycerol

  7. Saturated fatty acid Unsaturated H C R fatty acid 2 1 R 2 Polar H C R 2 3 head group R : 3 CH CH 2 2 CH CH NH 2 2 2 (Glycero)Phospholipids O O O C } C O CH O O P O OH Phosphatidic acid H Phosphatidylglycerol CH OH OH Phosphatidylethanolamine

  8. More (glycero)Phospholipids

  9. Sphingosine

  10. Sphingosine amide: ceramide CH 3 CH CH CH 2 2 3 CH 3 Some Typical Sphingolipids } X: O Sphingomyelin (PC) P O N O Glucosylcerebroside Glucose Ganglioside Complex oligosaccharide

  11. (glyco) Sphingolipids

  12. A 1 A 2 O X O P O O Lipid Analysis • Extraction • Use CCl4/MeOH • Hydrolysis (saponification) • Mild alkali ester breakage • Specific phospholipases D C Analysis TLC, GC-MS, HPLC

  13. Sterols Isoprene unit: Other sterols: Ergosterol (fungi) Sitosterol (plants)

  14. Ubiquinone H CO CH 3 3 H CO 3 H C 3 H CO CH 3 3 H C CH 3 2 H CO CH 3 2 Lipids as Electron Carriers O n O + 2H -2H O OH R R O OH Plastoquinone

  15. Vitamin K and Blood Clotting • Vitamin K1 • Essential in prothrombin synthesis

  16. Carboxyglutamate formation

  17. Carotenoid Pigments -carotene

  18. Lipids in Biosignaling • Structural variety • Insolubility • Protein carriers • Hydroxylation, etc. solubility • Location • Often in membrane • Action • Often at membrane surface

  19. Some Steroid Hormones

  20. Metabolism of Vitamin D: I

  21. Metabolism of Vitamin D: I

  22. Changes Specific 1,25-D 3 expression receptor of certain genes 1,25-Dihydroxy- cholecalciferol Metabolism of D3: II OH Many steps HO OH

  23. Vitamin A Metabolism

  24. Vitamin A Metabolism

  25. 11 -cis retinal (in rhodopsin) all trans retinal Vitamin A (Retinal) in Vision 11 12 10 (+) C light N H H H (+) N C H

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