Organic Chemistry, 6th edition Paula Yurkanis Bruice Chapter 26 The Organic Chemistry of the Metabolic Pathways Brian L. Groh Minnesota State University, Mankato Mankato, MN Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

What is the 3rd stage of catabolism? 26.5 What is the 3rd stage of catabolism? Oxidative phosphorylation The citric acid cycle Gluconeogenesis Fats, carbohydrates, and proteins are hydrolyzed to fatty acids, monosaccharides, and amino acids Fatty acids, monosaccharides, and amino acids are converted into compounds which enter the citric acid cycle Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

What is the 3rd stage of catabolism? 26.5 What is the 3rd stage of catabolism? Oxidative phosphorylation – 4th stage The citric acid cycle – 3rd stage Gluconeogenesis Fats, carbohydrates, and proteins are hydrolyzed to fatty acids, monosaccharides, and amino acids – 1st stage Fatty acids, monosaccharides, and amino acids are converted into compounds which enter the citric acid cycle – 2nd stage Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

How many acetyl-CoA’s are produced upon catabolism of myristic acid? 26.6 How many acetyl-CoA’s are produced upon catabolism of myristic acid? 6 7 8 12 14 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

How many acetyl-CoA’s are produced upon catabolism of myristic acid? 26.6 How many acetyl-CoA’s are produced upon catabolism of myristic acid? 6 7 8 12 14 Myristic acid is a C14 fatty acid. Each passage through the four reactions of beta-oxidation removes two carbons from the fatty acetyl-Co-A by converting them into the two carbon unit acetyl-CoA. Six cycles are required which results in the formation of 7 acetyl-CoA’s. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.6 Each pass of a fatty acid through the beta-oxidation cycle removes ________. 1 carbon 2 carbons 3 carbons 4 carbons divides the molecule in half Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.6 Each pass of a fatty acid through the beta-oxidation cycle removes ________. 1 carbon 2 carbons 3 carbons 4 carbons divides the molecule in half Each passage through the cycle removes two carbons from the fatty acyl-CoA by converting them into acetyl-CoA. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.7 What enzyme is required for the conversion of 3-phosphoglycerate to 2-phosphoglycerate? Kinase Mutase Transferase Hydroxylase Synthetase Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.7 What enzyme is required for the conversion of 3-phosphoglycerate to 2-phosphoglycerate? Kinase Mutase Transferase Hydroxylase Synthetase A mutase catalyzes a reaction in which a group is transferred from one part of the molecule to another part of the same molecule. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.10 Which of the following compounds can directly enter the citric acid cycle? Pyruvate Lactate Acetyl-CoA 2-phosphoglycerate Glycerol-3-phosphate Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.10 Which of the following compounds can directly enter the citric acid cycle? Pyruvate Lactate Acetyl-CoA 2-phosphoglycerate Glycerol-3-phosphate In addition to acetyl-CoA the intermediates, citrate, isocitrate, alpha-keto-glutarate, succinyl-CoA, succinate, fumarate, (S)-malate and oxaloacetate can enter the citric acid cycle. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.11 How many ATP’s are produced upon catabolism and oxidative phosphorylation of myristic acid? 7 14 28 77 84 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 26.11 How many ATP’s are produced upon catabolism and oxidative phosphorylation of myristic acid? 7 14 28 77 84 Catabolism of myristic acid (C14) yields 7 acetyl-CoA’s. Every molecule of acetyl-CoA that enters the citric acid cycle produces 12 ATP’s. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.