Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 24.6, Problem 18P
Ethanolamine ammonia lyase, a coenzyme B12–requiring enzyme, catalyzes the following reaction. Propose a mechanism for this reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
propose a mechanism for the following transformations
Can you draw the mechanism for the synthesis of cyclohexene from cyclohexanol through an acid-catalyzed dehydration reaction. Where
Phosphoric acid donates a proton ((H^+)) to the hydroxyl group of cyclohexanol, forming a protonated cyclohexanol intermediate. • The protonated cyclohexanol undergoes dehydration, leading to the removal of a water molecule and the formation of cyclohexene. • The released proton combines with water to form hydronium ion (H3O+), regenerating the catalyst.
The mechanism should illustrate the acid-catalyzed dehydration process, where phosphoric acid facilitates the removal of water from cyclohexanol, resulting in the formation of cyclohexene.
Proline betaine is a putative osmoprotectant in plants and bacteria, helping
to prevent dehydration of cells.
Coo-
CH, CH,
Propose a plausible pathway for biosynthesis of this compound.
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.2 - How many conjugated double bonds are there in a....Ch. 24.2 - Instead of adding to the 4a position and...Ch. 24.2 - Prob. 7PCh. 24.3 - Prob. 8PCh. 24.3 - Acetolactate synthase is another TPP-requiring...Ch. 24.3 - Acetolactate synthase transfers the acyl group of...Ch. 24.5 - Prob. 12PCh. 24.5 - The enzyme that catalyzes the C C bond cleavage...
Ch. 24.5 - Propose a mechanism for the ,-elimination reaction...Ch. 24.5 - Which compound is more easily decarboxylated?Ch. 24.5 - Explain why the ability of PLP to catalyze an...Ch. 24.5 - Explain why the ability of PLP to catalyze an...Ch. 24.6 - Ethanolamine ammonia lyase, a coenzyme...Ch. 24.6 - Prob. 19PCh. 24.7 - How do the structure of tetrahydrofolate and...Ch. 24.7 - What is the source of the methyl group in...Ch. 24.8 - Thiols such as ethanethiol and propanethiol can be...Ch. 24 - How does the metal ion in carboxypeptidase A...Ch. 24 - Prob. 23PCh. 24 - Prob. 24PCh. 24 - Prob. 25PCh. 24 - S-Adenosylmethionine (SAM) is formed from the...Ch. 24 - Prob. 27PCh. 24 - What acyl groups have we seen transferred by...Ch. 24 - Propose a mechanism for the following reaction:Ch. 24 - When transaminated, the three branched-chain amino...Ch. 24 - Draw the products of the following reaction, where...Ch. 24 - When UMP is dissolved in T2O, exchange of T for H...Ch. 24 - Dehydratase is a PLP-requiring enzyme that...Ch. 24 - In addition to the reaction mentioned in Section...Ch. 24 - PLP can catalyze both ,-elimination reactions...Ch. 24 - The glycine cleavage system is a group of four...Ch. 24 - Prob. 37PCh. 24 - FADH2 reduces , -unsaturated thioesters to...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The reagent diisobutylaluminum hydride (DIBALH) reduces esters to aldehydes. When nitriles are treated with DIBALH followed by mild acid hydrolysis, the product is also an aldehyde. Propose a mechanism for this reduction.arrow_forwardWhen dichloromethane is treated with strong NaOH, an intermediate is generated that reacts like a carbene. Draw the structure of this reactive intermediate, and propose a mechanism for its formation.arrow_forwardAcetylcholine esterase is an important enzyme in neural synaptic signal transmission. It breaks down the neurotransmitter acetylcholine after it binds the acetylcholine receptor. Its active site has the same features used by serine proteases. Here is the reaction catalyzed by Acetylcholine esterase: Acetylcholine Choline OH Acetate + H Acetylcholine is an ester, while peptide bonds cleaved by proteases are amides. How should acetylcholine estease's mechanism accommodate this? This cannot be determined from the information presented in class and in this question. For amides, the amide nitrogen is deprotonate to make it more like an ester. The same mechanism cleaves deprotonated amides and esters. No changes are needed. The mechanism same works for esters and amides. Prior to cleavage, a transamination converts the ester to an amide. The esterase will make a covalent intermediate to an amine to create the amide to be cleaved.arrow_forward
- An α, β-unsaturated carbonyl compound can be prepared by a reaction known as a selenenylation–oxidation reaction. A selenoxide is formed as anintermediate. Propose a mechanism for the reaction.arrow_forwardIf the following compound is saponified with sodium hydroxide, the products are: O || CH3(CH2) 14CH2-C-O-CH₂CH3 an ester and an alcohol an alcohol and a salt an acid and a salt an acid and an alcohol The purpose of the acid catalyst in the hydrolysis of an amide is: to enhance the nucleophilicity of the water molecule to enhance the electrophilicity of the amide carbonyl carbon to enhance the electrophilicity of the water molecule to shift the equilibrium of the reaction Which of the following compounds has the highest boiling point? CH3CH3 CH3CH2OH CH3-0-CH3 CH3COOHarrow_forwardPropose an appropriate intermediate for the following reactionarrow_forward
- Hydroxylamine, H2NOH, has both an OH functional group and an NH2 functional group, so it can feasibly undergo reaction with a ketone or an aldehyde to produce either an acetal or an imine-like compound called an oxime. (a) Draw each of these mechanisms for the reaction of hydroxylamine with acetone. (b) Which is the major product? Hint: Which step decides the outcome?arrow_forwarda OH CH2CNHCH3 T CH3 d OH CHCHNHCH3 CH3 Ephedrine can be synthesized via reductive amination plus other necessary reactions. Predict the necessary reactants and reagents that will give the intermediate and final products shown.arrow_forwardTo propose an intermediate and mechanism for the transformationsarrow_forward
- propose a mechanism for the following transformationarrow_forwardProvide a synthesis pathway to get the productsarrow_forwardThe mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License