Chem 109 C Fall 2014 Armen Zakarian ffice: Chemistry Bldn 2217
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
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
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
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
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
Chapter 25 PRACTICE PRBLEM What carbon atoms of glucose end up in ethanol under anaerobic conditions in yeast? 7
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
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
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
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
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
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
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
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
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
Chapter 25 NADH 2.5 ATP FADH 2 1.5 ATP 17
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
Chapter 25, brief summary pyruvate + C 2 pyruvate dehydrogenase system, [+1 NADH]! 2C 2 + CoASH [+ 1 ATP, + 3 NADH, + 1 FADH 2 ] 19
Chapter 25, brief summary stage 4 of catabolism: NADH 2.5 ATP FADH 2 1.5 ATP 20
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Chapter 27, Lipids PRACTICE PRBLEM 26 When pyruvate is reduced by NADH to lactate, which hydrogen in lactate comes from NADH? 22