Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 29.SE, Problem 51AP
In glycerol
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List the following in order of increasing tendency to accept electrons: (a) α-ketoglutarate + CO2 (yielding isocitrate); (b) oxaloacetate; (c) O2; (d) NADP+.
draw the chemical structures of the reactant and product of the following reactions:
a.) addition of a phosphate group to (ex: phosphorylation of) glycose
b.) addition of a phosphate group to (ex: phosphorylation of) fructose-6-phosphate
c.) addition of a phosphate group to (ex: phosphorylation of) phosphoenolpyruvate
The vitamin Niacin is used to form nicotinamide adenosine dinucleotide, which readily shuttles between its oxidized (NAD+) and reduced (NADH) forms. The latter serves as a cellular equivalent to NaBH4. The essential portions of the structures are shown below. Outline a mechanism for the cellular conversion of pyruvate to lactate. (Note: like NaBH4, NADH cannot reduce carboxylic acid carbonyls).
Chapter 29 Solutions
Organic Chemistry
Ch. 29.1 - Prob. 1PCh. 29.3 - Write the equations for the remaining passages of...Ch. 29.3 - Prob. 3PCh. 29.4 - Write a mechanism for the dehydration reaction of...Ch. 29.4 - Evidence for the role of acetate in fatty-acid...Ch. 29.4 - Does the reduction of acetoacetyl ACP in step 6...Ch. 29.5 - Prob. 7PCh. 29.5 - Look at the entire glycolysis pathway, and make a...Ch. 29.6 - Prob. 9PCh. 29.7 - Prob. 10P
Ch. 29.7 - Write mechanisms for step 2 of the citric acid...Ch. 29.7 - Prob. 12PCh. 29.8 - Prob. 13PCh. 29.9 - Write all the steps in the transamination reaction...Ch. 29.9 - What -keto acid is formed on transamination of...Ch. 29.9 - Prob. 16PCh. 29.SE - Prob. 17VCCh. 29.SE - Identify the following intermediate in the citric...Ch. 29.SE - The following compound is an intermediate in the...Ch. 29.SE - Prob. 20VCCh. 29.SE - In the pentose phosphate pathway for degrading...Ch. 29.SE - Prob. 22MPCh. 29.SE - One of the steps in the pentose phosphate pathway...Ch. 29.SE - One of the steps in the pentose phosphate pathway...Ch. 29.SE - Prob. 25MPCh. 29.SE - Prob. 26MPCh. 29.SE - Prob. 27MPCh. 29.SE - Prob. 28MPCh. 29.SE - Prob. 29MPCh. 29.SE - Prob. 30MPCh. 29.SE - Prob. 31MPCh. 29.SE - Prob. 32APCh. 29.SE - Prob. 33APCh. 29.SE - Prob. 34APCh. 29.SE - Prob. 35APCh. 29.SE - Prob. 36APCh. 29.SE - Prob. 37APCh. 29.SE - Prob. 38APCh. 29.SE - Prob. 39APCh. 29.SE - Prob. 40APCh. 29.SE - Prob. 41APCh. 29.SE - Prob. 42APCh. 29.SE - Prob. 43APCh. 29.SE - Prob. 44APCh. 29.SE - Prob. 45APCh. 29.SE - Prob. 46APCh. 29.SE - Prob. 47APCh. 29.SE - Prob. 48APCh. 29.SE - Prob. 49APCh. 29.SE - Prob. 50APCh. 29.SE - In glycerol metabolism, the oxidation of...Ch. 29.SE - Prob. 52APCh. 29.SE - Prob. 53APCh. 29.SE - Prob. 54APCh. 29.SE - In step 7 of fatty-acid biosynthesis (Figure...Ch. 29.SE - Prob. 56AP
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- The aconitase-catalyzed addition of water to cis-aconitate in the citric acid cycle occurs with the following stereochemistry. Does the addition of the OH group occur on the Re or Si face of the substrate? What about the addition of the H? Do the H and OH groups add from the same side of the double bond or from opposite sides?arrow_forwardOne of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose 5-phosphate with ribose 5-phosphate in the presence of a transketolase to give glyceraldehyde 3-phosphate and sedoheptulose 7-phosphate. (a) The first part of the reaction is nucleophilic addition of thiamin diphosphate (TPP) ylide to xylulose 5-phosphate, followed by a retro-aldol cleavage to give glyceraldehyde 3-phosphate and a TPPcontaining enamine. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is addition of the enamine to ribose 5-phosphate followed by loss of TPP ylide to give sedoheptulose 7-phosphate. Show the mechanism.arrow_forwardOne of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of sedoheptulose 7-phosphate with glyceraldehydes 3-phosphate in the presence of a transaldolase to yield erythrose 4-phosphate and fructose 6-phosphate. (a) The first part of the reaction is the formation of a protonated Schiff base of sedoheptulose 7-phosphate with a lysine residue in the enzyme followed by a retro-aldol cleavage to give an enamine plus erythrose 4-phosphate. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is a nucleophilic addition of the enamine to glyceraldehyde 3-phosphate followed by hydrolysis of the Schiff base to give fructose 6-phosphate. Show the mechanism.arrow_forward
- Propose a mechanism for the formation of fructose-1,6-bisphosphate from dihydroxyacetone phosphate and glyceraldehyde-3-phosphate, using hydroxide ion as the catalyst.arrow_forwardWhich of the reactions are spontaneous (favorable)? 1)DHAP↽−−⇀glyceraldehyde-3-phosphateΔ?=3.8 kJ/mol 2)L-malate+NAD+⟶oxaloacetate+NADH+H+Δ?=29.7 kJ/mol- 3) glutamate+NAD++H2O⟶NH+4+α-ketoglutarate+NADH+H+Δ?=3.7 kcal/ 4) C6H13O9P+ATP⟶C6H14O12P2+ADPΔ?=−14.2KJ/mol 5) −Rh(I)C2H6Δ?=−150.97 kJ/molC2H4+H2→Rh(I)C2H6ΔG=−150.97 kJ/mol 6) C4H4O5⟶C4H2O4+H2OΔ?=3.1 kJ/molarrow_forwardThe final step in the metabolic degradation of uracil is the oxidation of malonic semialdehyde to give malonyl CoA. Propose a mechanism.arrow_forward
- Triose phosphate isomerase catalyzes the conversion of dihydroxyacetone phosphate (DHAP) into glyceraldehyde-3-phosphate (G3P). Which of the following illustrates this chemical reaction? a) A b) B c) C d) Darrow_forwardGiven the following information on reduction potentials, calculate the standard free energy in kJ/mol based on your understanding of electron transfer through the pyruvate dehydrogenase complex. Round to nearest whole number. Lipoamide + 2H+ + 2e- → dihydrolipoamide ∆εο = -0.29 FAD + 2H+ + 2e- → FADH2 ∆εο = −0.01arrow_forwardPyruvate carboxylase is thought to activate CO2 by ATP, through formation of carboxyphosphate as an intermediate. Propose a mechanism for the formation of this intermediate.arrow_forward
- In one of the steps in this pathway fructose 1,6-biphosphate (F1,6BP) is converted to gylceraldehyde-3-phosphate (G-3-p) and dihydroxyacetone phosphate (DHAP). This reaction is catalyzed by the enzyme aldolase. For this reaction at 25 celcuius and Ph7 we have: Keq= 10-4M and Delta G = +5456 cal/mol Calculate the following: The concentration of F1, 6BP, DHAP and G-3-P at equilibrium when the initial F1,6BP is (A) 1M, (b) 10-2 M, (c) 2 X 10*4 M and (d) 10-5 M. I been trying to solve this problem but I dont even know where to begin with. Atleast help me with problem A, I would be able to guide myself through.arrow_forwardIn glycolysis, why must glucose-6-phosphate isomerize to fructose-6-phosphate before the cleavage reaction with aldolase occurs?arrow_forwardWhat is the standard free energy (∆G0’) for the reduction of coenzyme Q by NADH as carried out by Complex I (NADH-CoQ Reductase) of the electron transport pathway if E0’(NAD+/NADH) =-0.10 V and E0’ (CoQ/CoQH2) = +0.095 V. Answer Choicesarrow_forward
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