1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids3h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

25. Condensation Chemistry

Condensation Reactions

Organic Chemistry

25. Condensation Chemistry

Condensation Reactions

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1:29 minutes

Problem 15fBruice - 8th Edition

Textbook Question

The following compound has been found to be an inhibitor of penicillinase. The enzyme can be reactivated by hydroxylamine (NH2OH). Propose a mechanism to account for the reactivation.

Verified step by step guidance

Identify the functional groups in the inhibitor that could interact with hydroxylamine (NH2OH). Look for electrophilic centers that could be attacked by the nucleophilic NH2OH.

Consider the role of hydroxylamine as a nucleophile. It can attack electrophilic carbon atoms, such as those in carbonyl groups, to form a new bond.

Propose the initial nucleophilic attack by NH2OH on the electrophilic center of the inhibitor, leading to the formation of a tetrahedral intermediate.

Analyze the possible breakdown of the tetrahedral intermediate, which could result in the release of the enzyme from the inhibitor, thus reactivating the enzyme.

Consider any additional steps that might stabilize the final product or regenerate the active form of the enzyme, ensuring that the mechanism is consistent with known chemical principles.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Enzyme Inhibition

Enzyme inhibition refers to the process by which a molecule (inhibitor) decreases or halts the activity of an enzyme. In the context of penicillinase, an enzyme that breaks down penicillin, inhibitors can bind to the enzyme and prevent it from catalyzing its reaction. Understanding the type of inhibition (competitive, non-competitive, or irreversible) is crucial for proposing mechanisms of reactivation.

Mechanism of Hydroxylamine Reactivation

Hydroxylamine (NH2OH) is known to reactivate certain enzymes by modifying specific amino acid residues in the enzyme's active site. In the case of penicillinase, hydroxylamine can form a covalent bond with the enzyme, potentially restoring its active conformation. This reactivation mechanism often involves nucleophilic attack by hydroxylamine on electrophilic centers within the enzyme.

Covalent Modification

Covalent modification is a biochemical process where a functional group is added to an enzyme, altering its activity. This can include phosphorylation, acetylation, or, as in this case, the addition of hydroxylamine. Understanding how covalent modifications can either inhibit or reactivate enzyme function is essential for proposing a detailed mechanism for the reactivation of penicillinase.