2pp_1.FattyAcids - BIOCHEMISTRY 441 Winter 2010 Bill Parson...

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1/8/2010 1 BIOCHEMISTRY 441 Winter, 2010 Bill Parson & Ted Young 1. Biosynthesis of fatty acids 2. Triacylglycerols, phospholipids & complex lipids 3. Cholesterol & lipoproteins 4. Photosynthesis: antennas & reaction centers 5. Photosynthesis: electron transfer & photophosphorylation 6. Photosynthesis: carbon fixation by C 3 and C 4 pathways 7. Amino acid metabolism: transamination and NH 3 transport 8. Urea cycle, amino acid catabolism & biosynthesis 9. Aromatic amino acids & neurotransmitters 10. One-carbon metabolism 11. Biosynthesis of pyrimidines & purines 12. Deoxyribonucleotide biosynthesis & nucleotide catabolism 13. DNA and RNA structure PowerPoint and pdf files of the lectures are available on the course website: http://courses.washington.edu/bioc441/index.shtml On-line video screencast recordings of the classes are located at: http://www.css.washington.edu/course/BIOC441A To watch a Screencast, right-click the Screencast link. Adobe Flash Player is required. Visit the Adobe Flash Player Download Center if Flash is not installed on your computer: http://www.adobe.com/products/flashplayer/
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1/8/2010 2 Fatty acids have extended hydrocarbon chains Most natural fatty acids have an even number of carbons. Most natural unsaturated fatty acids have cis double bonds. stearic acid, C18:0 CO 2 H CO 2 H palmitic acid, C16:0 oleic acid, C18:1( Δ 9 ) CO 2 H 10 9 10 9 CO 2 H palmitoleic acid, C16:1( Δ 9 ) 1 1 1 1 16 18 16 18 Fatty acids are components of phospholipids and triacylglycerols glycerophospholipids Phospholipid bilayers are the central structural elements of biological membranes. triacylglycerols Triacylglycerols are stored as energy reserves. Fatty acids also are found as cholesterol esters in lipoproteins, and are attached covalently to some proteins. sphingolipids Sphingolipids on cell surfaces are sites of cell recognition. Inositol phospholipids participate in intracellular signaling. R ′- C - OCH O CH 2 O - C - R O CH 2 O - P - OCH 2 CH 2 - N(CH 3 ) 3 + O - O CH 2 O - C - R O R ′- C - OCH CH 2 O - C - R ′′ O O HOCH-CH=CH-CH 2 R CH 2 O - P - OCH 2 CH 2 - N(CH 3 ) 3 + O - O R -C -NH-CH O
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1/8/2010 3 Fatty acids are synthesized from acetyl-CoA in adipose tissue & the liver CH 3 - C - S -CoA O ATP, NADPH, CO 2 palmitic acid (C16:0) palmitoylCoA H 3 C C - S -CoA O stearic acid (C18:0) stearoylCoA H 3 C C - S -CoA O The labeling patterns suggest that the fatty acid chain forms by successive addition of two-carbon units 9 1 H 3 C oleic acid (C18:1 Δ 9 ) oleoylCoA C - S -CoA O 18 Why is CO 2 needed?
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1/8/2010 4 CH 3 - C -S-CoA O - O 2 C - CH 2 - C -S-CoA O malonylCoA ATP P i ADP HCO 3 - bound biotin O NH HN S C O=C NH O NH HN S C O=C NH O N- CO 2 - HN S C O=C NH biotin- carboxylase site carboxyl- transferase site biotin attachment site MalonylCoA serves as the donor of two-carbon units MalonylCoA is formed from acetylCoA and CO 2
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