Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 18, Problem 46P
Aldolase shows no activity if it is incubated with iodoacetic acid before fructose-1, 6-bisphosphate is added to the reaction mixture. What could cause this loss of activity?
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Imidazoleglycerol‑phosphate dehydratase is an enzyme in the histine biosynthesis pathway. It catalyzes the E1 dehydration of D‑erthyro‑imidazole‑glycerol phosphate to imidazole acetol‑phosphate. This is a rare example of a biological E1 reaction, as most biological elimination reactions occur through E1cB instead.
In this reaction, D‑erthyro‑imidazole‑glycerol phosphate is first protonated to form a good leaving group. Then, the leaving group is ejected to form the resonance‑stabilized carbocation shown. Draw curved arrows forming the most stable resonance structure to explain why this reaction goes through an E1 mechanism.
Draw curved arrows to form the most stable resonance structure.
Aldolase shows no activity if it is incubated with iodoacetic acid before fructose-1,6-bisphosphate is added to the reaction mixture. What causes this loss of activity?
4. The AGo for the aldolase reaction is 22.8 kJ/mol. When the reaction is run in a hepatocyte cell at
37°C, the concentrations of the intermediates are: fructose 1,6-bisphosphate =1.41 x 103 M,
glyceraldehyde 3-phosphate 2.95 x 10-6 M, and dihydroxyacetone phosphate = 1.62 x 10-5 M.
Calculate the free energy change for this reaction
Is this reaction thermodynamically favorable
Chapter 18 Solutions
Essential Organic Chemistry, Global Edition
Ch. 18.1 - Prob. 1PCh. 18.2 - If H218O were used to hydrolyze lysozyme, which...Ch. 18.3 - Which of the following amino acid side chains can...Ch. 18.3 - Arginine and lysine side chains fit into trypsins...Ch. 18.4 - Which of the following amino acid side chains can...Ch. 18.4 - Prob. 6PCh. 18.5 - Prob. 7PCh. 18.5 - Draw the mechanism for the hydroxide-ion-catalyzed...Ch. 18.5 - What advantage does the enzyme gain by forming an...Ch. 18.7 - Prob. 10P
Ch. 18.7 - Prob. 11PCh. 18.8 - How many conjugated double bonds are there in a....Ch. 18.8 - Instead of adding to the 4a-position and...Ch. 18.8 - In succinate dehydrogenase, FAD is covalently...Ch. 18.8 - Prob. 15PCh. 18.9 - Acetolactate synthase is another TPP-requiring...Ch. 18.9 - Acetolactate synthase can also transfer the acyl...Ch. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 21PCh. 18.11 - Prob. 23PCh. 18.11 - Which compound is more easily decarboxylated?Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.12 - What groups are interchanged in the following...Ch. 18.13 - Why is the coenzyme called tetrahydrofolate?Ch. 18.13 - What amino acid is formed by the following...Ch. 18.13 - How do the structures of tetrahydrofolate and...Ch. 18.13 - What is the source of the methyl group in...Ch. 18 - Prob. 32PCh. 18 - Prob. 33PCh. 18 - From what vitamins are the following coenzymes...Ch. 18 - Prob. 35PCh. 18 - For each of the following reaction, name both the...Ch. 18 - Explain why serine proteases do not catalyze...Ch. 18 - Prob. 38PCh. 18 - For each of the following enzyme catalyzed...Ch. 18 - Trisephosphate isomerase (TIM) catalyzes the...Ch. 18 - Prob. 41PCh. 18 - What acyl groups have we seen transferred by...Ch. 18 - When UMP is dissolved in T2O, exchange of T for H...Ch. 18 - Prob. 44PCh. 18 - When transaminated, the three branched-chain amino...Ch. 18 - Aldolase shows no activity if it is incubated with...
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- One 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_forwardTPP is a coenzyme for transketolase, the enzyme that catalyzes the conversion of a ketopentose (xylulose5-phosphate) and an aldopentose (ribose-5-phosphate) to an aldotriose (glyceraldehyde-3-phosphate) and a ketoheptose (sedoheptulose-7-phosphate). Notice that the total number of carbons in the reactants and products is the same (5 + 5 = 3 + 7). Propose a mechanism for this reaction.arrow_forward4. Liver alcohol dehydrogenase (LADH) catalyzes a reversible, pH-dependent oxidation of an alcohol to an aldehyde according to the following reaction: LADH RCH2OH + NAD* RCHO + NADH + H* where NAD* and NADH are, respectively, the oxidized and reduced forms of the cofactor nicotin-amide adenine dinucleotide. While the reaction is actually a two-substrate reaction, it proceeds like a one- substrate reaction through a so-called compulsory-ordered ternary complex mechanism. It has been shown through kinetic studies that, in the case of primary alcohols, the enzyme binds first the cofactor forming a binary enzyme-NAD* complex that then binds the second substrate, the alcohol, to form a ternary enzyme-NAD*-substrate complex in which the oxidation of the alcohol proceeds with reduction of the cofactor. While the enzyme catalyzes oxidation of various steroids as well as ingested ethanol, it also catalyzes the oxidation of methanol CH3OH, forming the extremely toxic product formaldehyde HCHO.…arrow_forward
- In the glycolytic pathway, a six-carbon sugar (fructose 1,6-bisphosphate) is cleaved to form two three-carbon sugars, which undergo further metabolism . In this pathway, an isomerization of glucose 6-phosphate tofructose 6-phosphate (shown below) occurs two steps before the cleavage reaction (the intervening step is phosphorylation of fructose 6-phosphate to fructose 1,6-bisphosphate ). What does the isomerization step accomplish from a chemical perspective? (Hint: Consider what might happen if the C—C bond cleavage were to proceed without the preceding isomerization.)arrow_forwardIf an enzyme-catalyzed reaction has a high rate at low pH and low rate at higher pH, this implies that a group on either the enzyme or the substrate must be for an efficient reaction. leaving group oxidoreductase coenzymes O protonated deprotonated The compound that consists of deoxyribose linked by an N-glycosidic bond to N-9 of guanine is: adenylate deoxyguanosine guanosine nucleotide guanylatearrow_forwarda Lactate dehydrogenase H H3C-C-coO- ОН ooc-C-CH3 L-(+)-Lactase Pyruvate This is a(an) b Creatine kinase CH3 O CH3 O H2N, АТР ADP NH2 NH2 Adenosine triphosphate Adenosine diphosphate Creatine Phosphocreatine This is a(an)arrow_forward
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- TPP is a coenzyme for transketolase, the enzyme that catalyzes the conversion of a ketopentose (xylulose- 5-phosphate) and an aldopentose (ribose-5-phosphate) to an aldotriose (glyceraldehyde-3-phosphate) anda ketoheptose (sedoheptulose-7-phosphate). Notice that the total number of carbons in the reactants and products is the same (5 + 5 = 3 + 7). Propose a mechanism for this reaction.arrow_forwardCholesterol-lowering drugs commonly target O HMG-COA synthase, the enzyme that catalyzes the synthesis of mevalonate O pyruvate decarboxylase complex, which catalyzes the synthesis of acetyl-CoA O mevalonate, an isoprene O HMG-COAreductase, the rate-limiting enzyme in cholesterol biosynthesis O HMG-CoA synthase, the enzyme that catalyzes the first step in cholesterol biosynthesisarrow_forwardIn the 1st reaction of citric acid cycle, acetyl CoA and oxaloacetate are combined to form citrate as shown below. What is the best way to describe this reaction? CH acetyl Col CH₂ co exaloncertate HO citrate synthase ço, CH₂ HO-C-00 CH₂ co₂ citrate O It begins with an Aldol reaction followed by hydrolysis of CoA thioester). It begins with a keto-enol tautomerization followed by an Aldol reaction. It involves a Claisen condentation. OIt involves an Aldol condensation. None of the abovearrow_forward
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