Chem 109 C. Fall Armen Zakarian Office: Chemistry Bldn 2217

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1 Chem 109 C Fall 2014 Armen Zakarian ffice: Chemistry Bldn 2217

2 Chapter 25 o Glycolysis : fates of pyruvate NADH, H + H + C 2 NADH, H + H - (S)-lactic acid lactate dehydrogenase; anaerobic conditions - pyruvate pyruvate decarboxylase, TPP anaerobic, yeast alcohol dehydrogenase H pyruvate dehydrogenase system; aerobic conditions 2

3 Chapter 25 o Glycolysis : fates of pyruvate NADH, H + H + C 2 NADH, H + H - (S)-lactic acid lactate dehydrogenase; anaerobic conditions - pyruvate pyruvate decarboxylase, TPP anaerobic, yeast alcohol dehydrogenase H pyruvate dehydrogenase system; aerobic conditions PRACTICE PRBLEM Provide a mechanism for the reduction of acetaldehyde to ethanol with NADH. 3

4 o Catabolism of proteins: amino acids Chapter 25 - NH + 3 phenylalanine hydroxylase H - NH + 3 tyrosine aminotransferase PLP H - MECHANISM? phenylalanine tyrosine p-hydroxyphenylpyruvate p-hydroxyphenylalanine dioxygenase - H homogentisate - C + fumarate 4

5 o Catabolism of proteins: amino acids Chapter 25 - NH + 3 phenylalanine hydroxylase H - NH + 3 tyrosine aminotransferase PLP H - MECHANISM? phenylalanine tyrosine p-hydroxyphenylpyruvate oxidation decarboxylation p-hydroxyphenylalanine dioxygenase H H H - H epinephrine (adrenaline) NH 2 CH 3 homogentisate - C + fumarate 5

6 Chapter 25 PRACTICE PRBLEM Heptadecanoic, or margaric acid is a saturated fatty acid found in the fat and milkfat of ruminants. Its complete metabolism gives 7 equivalents of and one equivalent of propionyl-coa. Metabolism of propionyl-coa includes two reactions giving succinyl-coa, which is a citric cycle intermediate. Identify the coenzyme required for each step. - C propionyl-coa methylmalonyl-coa succinyl-coa 6

7 Chapter 25 PRACTICE PRBLEM What carbon atoms of glucose end up in ethanol under anaerobic conditions in yeast? 7

8 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 8

9 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 9

10 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 10

11 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 11

12 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 12

13 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 13

14 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 14

15 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 15

16 H 2 NADH, H + 8 H - C (S)-malate 7 - C H 2 oxaloacetate 1 CoASH H citrate citric acid cycle 2 1. eliminate H 2 2. add H 2 H isocitrate 3 Chapter 25 NADH, H +, C 2 - C fumarate FADH 2 FAD 6 - C 5 4 α-ketoglutarate, CoASH succinate GTP, CoASH succinyl-coa GDP, HP 2-3 NADH, H +, C 2 16

17 Chapter 25 NADH 2.5 ATP FADH ATP 17

18 Chapter 25, brief summary Catabolism: fats 3 fatty acids + 1 glycerol glycerol DHA pyruvate [+1 ATP, +2 NADH] fatty acid fatty acyl-coa [-1 ATP] fatty acyl-coa [+1 FADH 2, +1 NADH] {β-oxidation} per 1 β-oxidation carbohydrates monosaccharides: glucose glycolysis - 10 reactions glucose 2 pyruvates [+ 2 ATP, + 2 NADH] proteins amino acids pyruvate, etc. 18

19 Chapter 25, brief summary pyruvate + C 2 pyruvate dehydrogenase system, [+1 NADH]! 2C 2 + CoASH [+ 1 ATP, + 3 NADH, + 1 FADH 2 ] 19

20 Chapter 25, brief summary stage 4 of catabolism: NADH 2.5 ATP FADH ATP 20

21 21.

22 Chapter 27, Lipids PRACTICE PRBLEM 26 When pyruvate is reduced by NADH to lactate, which hydrogen in lactate comes from NADH? 22

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