Biochemistry: Concepts and Connections (2nd Edition)
2nd Edition
ISBN: 9780134641621
Author: Dean R. Appling, Spencer J. Anthony-Cahill, Christopher K. Mathews
Publisher: PEARSON
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Chapter 16, Problem 8P
2-Bromopalmitoyl-CoA inhibits the oxidation of palmitoyl-CoA by isolated mitochondria but has no effect on the oxidation of palmitoylcarnitine. What is the most likely site of inhibition by 2-bromopalmitoyl-CoA?
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2-Bromopalmitoyl-CoA inhibits the oxidation of palmitoyl-CoA by isolatedmitochondria but has no effect on the oxidation of palmitoylcarnitine. What is the most likely site of inhibition by 2-bromopalmitoyl-CoA?
1) Humans do not undergo net synthesis of carbohydrate from acetyl- CoA, yet carbons of acetyl -CoA can be incorporated into glucose and amino acids. Show pathways as to how this can happen.
2) A molecule -X inhibits oxidation of stearoyl-CoA by isolated mitochondria but has no effect on palmitoyl-carnitine oxidation, explain.
The products of pyrimidine base catabolism, β-alanine and β-aminoisobutyrate, can be further degraded to acetyl-CoA and succinyl-CoA, respectively. Can you suggest the types of reaction required to accomplish these transformations?
Chapter 16 Solutions
Biochemistry: Concepts and Connections (2nd Edition)
Ch. 16 - Prob. 1PCh. 16 - If palmitic acid is subjected to complete...Ch. 16 - Calculate the number of ATPs generated by the...Ch. 16 - Prob. 4PCh. 16 - Prob. 5PCh. 16 - Under conditions where ketone bodies are being...Ch. 16 - Prob. 7PCh. 16 - 2-Bromopalmitoyl-CoA inhibits the oxidation of...Ch. 16 - When the identical subunits of chicken liver fatty...Ch. 16 - Prob. 10P
Ch. 16 - Prob. 11PCh. 16 - Prob. 12PCh. 16 - Prob. 13PCh. 16 - Prob. 14PCh. 16 - Prob. 15PCh. 16 - What would be the effect on fatty acid synthesis...Ch. 16 - Prob. 17PCh. 16 - Identify and briefly discuss each mechanism...Ch. 16 - Prob. 19PCh. 16 - Prob. 20PCh. 16 - Prob. 21PCh. 16 - Prob. 22PCh. 16 - Prob. 23PCh. 16 - 24. If mevalonate labeled with 14C in the carboxyl...Ch. 16 - Prob. 25PCh. 16 - Identify a pathway for utilization of the four...Ch. 16 - Prob. 27PCh. 16 - cis-Vaccenate is an 18-carbon unsaturated fatty...Ch. 16 - 29. Briefly describe how cyclic AMP controls...Ch. 16 - Prob. 30PCh. 16 - Prob. 31PCh. 16 - In addition to the pathway described in Figure...Ch. 16 - Prob. 33P
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- The mechanism for the conversion from alpha kytoglutarate into succinyl CoA by alpha-ketoglutare dehydrogenase is analogous to the pyruvate dehydrogenase mechanism. Draw and show the major intermediates and arrow pushing for the enzyme-catalyze process for the conversion of alpha-ketoglutarate to succinyl CoA. Note: the carbanion of thiamine pyrophosphate nucleophillically attacks C-2 of the alpha-ketoglutarate, i.e., the carbonyl carbon of that substrate.arrow_forwardOne of the regulators of the TCA cycle is succinyl CoA. Discuss the rationale for this molecule to be used to regulate the TCA cycle [include chemical structures and chemical equations where appropriate]. What is an allosteric inhibitor? How does it operate? For what TCA enzymes does succinyl CoA act as an inhibitor? What is the metabolic role of succinyl CoA? So then why is this molecule a reasonable choice as an inhibitor of the TCA?arrow_forwardThe archaebacterium Haloarcula marismortui can use acetate (which is converted to acetyl-CoA) as a precursor for carbohydrate synthesis, but it lacks isocitrate lyase and therefore cannot use the glyoxylate pathway. Instead, it converts isocitrate to α-ketoglutarate, which is then converted to the amino acid methylaspartate in two more steps. This five-carbon compound is modifi ed and broken down to release glyoxylate. Describe the three reactions that lead from isocitrate to methylaspartate.arrow_forward
- One of the regulators of the TCA cycle is succinyl CoA. Discuss the rationale for this molecule to be used to regulate the TCA cycle. What is the metabolic role of succinyl CoA?arrow_forwardSeveral pathways exist in different organisms for the metabolism of propionyl-CoA. Most organisms utilizethe pathway that feeds into the citric acid cycle via succinyl-CoA. Another metabolic route used by Clostridium kluyveriis a "continuation of -oxidation" and consists of the following enzymatic reactions: (a) propionyl-CoA is converted toacryloyl-CoA; (b) formation of 3-hydroxypropionyl-CoA; (c) conversion to malonyl semialdehyde CoA; (d) productionof malonyl-CoA, which is then (e) decarboxylated to produce acetyl-CoA. Outline the above steps between propionylCoA and acetyl-CoA. Show structures for the metabolites and indicate appropriate cofactors (free or bound) that may beinvolved.arrow_forwardSome bacteria use the citric acid cycle intermediate, a-ketoglutarate, plus acetyl-CoA, as the starting point for lysine biosynthesis. The first part of this biosynthetic pathway uses the same chemical strategy found in the citric acid cycle. Propose a four-step pathway for the conversion of a-ketoglutarate to 2-oxoadipate. Draw the three missing intermediates, and indicate the chemistry involved in each reaction. Include any cofactors that you think might be required for specific steps.arrow_forward
- One of the regulators of the TCA cycle is succinyl CoA. Discuss the rationale for this molecule to be used to regulate the TCA cycle. For what TCA enzymes does succinyl CoA act as an inhibitor?arrow_forwardSeveral pathways exist in different organisms for the metabolism of propionyl-CoA. Most organisms utilizethe pathway that feeds into the citric acid cycle via succinyl-CoA. Another metabolic route used by Clostridium kluyveriis a "continuation of -oxidation" and consists of the following enzymatic reactions: (a) propionyl-CoA is converted toacryloyl-CoA; (b) formation of 3-hydroxypropionyl-CoA; (c) conversion to malonyl semialdehyde CoA; (d) productionof malonyl-CoA, which is then (e) decarboxylated to produce acetyl-CoA. Outline the above steps between propionylCoA and acetyl-CoA. Show structures for the metabolites and indicate appropriate cofactors (free or bound) that may beinvolved. b) Suggest a mechanism for enzyme reaction (e).arrow_forwardPhosphoglycerate mutase (PGM) catalyzes the interconversion of 3-phosphoglycerate (3PG) and 2-phosphoglycerate (2PG) in the glycolytic and gluconeogenic pathways. a) To what enzyme class does PGM belong? b) There are two distinct classes of PGM, one which is dependent on 2,3-bisphosphoglycerate (2,3-BPG), dPGM, and one which is not, iPGM. dPGM uses acid base chemistry and a phosphorylated histidine residue to interconvert 3PG and 2PG. The dPGM reaction proceeds with formation of 2,3-BPG as an intermediate. Propose a mechanism for the dPGM-catalyzed conversion of 3PG to 2PG that is consistent with this information. c) What is the purpose of 2,3-BPG (i.e., why does dPGM require it)?arrow_forward
- Discuss how hypoglycin (an unusual amino acid found in the unripened fruit of the akee tree) acts as a mechanism-based inhibitor of acyl-CoA dehydrogenase. What is a mechanism-based inhibitor? How is it different from a transition state analog? How is hypoglycin metabolized in the cell? What compound is formed? Include relevant chemical structures and reactions. How does the compound formed in part b inhibit acyl-CoA dehydrogenase? Include relevant chemical structures and reactions. Compare the mechanism of inhibition of β-oxidation by hypoglycin A with the mechanism of inhibition of the TCA by fluoroacetate.arrow_forwardHow many molecules of NADH and FADH2 are obtained from the b-oxidation of one molecule of a 16-carbon saturated fatty acyl-CoA?arrow_forwardFourteen NADPH molecules are required to produce one molecules of palmitic acid from acetyl CoA. Substantiate this statement by referring to the enzymatic activities involved in reduction steps during fatty acid synthesis and the number of cycles required to produce palmitic acid from acetyl CoA. How many molecules of ATP is required for the synthesis of palmitic acid from cytosolic acetyl-CoA?arrow_forward
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