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Related Concept Videos

Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

2.8K
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
2.8K
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

2.9K
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
2.9K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

15.4K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
15.4K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

10.2K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
10.2K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.1K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.1K
Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

7.2K
This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
7.2K

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Updated: Jul 6, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Mechanism-Based Enzyme Inactivation Using an Allyl Sulfoxide-Allyl Sulfenate Ester Rearrangement1.

Michael Johnston1, Ronald Raines1, Christopher Walsh1

  • 1Massachusetts Institute of Technology.

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|January 8, 2024
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Summary

A novel compound irreversibly inactivates bacterial enzymes involved in methionine metabolism. This mechanism-based inactivation is covalent and stoichiometric, but enzymes can be reactivated by thiols.

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Area of Science:

  • Biochemistry
  • Enzymology
  • Medicinal Chemistry

Background:

  • Pyridoxal phosphate (PLP)-dependent enzymes are crucial in amino acid metabolism.
  • Methionine biosynthesis and breakdown pathways are essential in bacteria.
  • Mechanism-based enzyme inactivation is a strategy for drug development.

Purpose of the Study:

  • To synthesize and characterize a novel inhibitor of PLP-dependent enzymes.
  • To elucidate the mechanism of inactivation for cystathionine γ-synthetase and methionine γ-lyase.
  • To explore the potential of this inhibitor for therapeutic applications.

Main Methods:

  • Chemical synthesis of 2-amino-4-chloro-5-(p-nitrophenylsulfinyl)pentanoic acid (1).
  • Enzyme activity assays to measure inactivation kinetics.
  • Radiolabeling studies with tritium to confirm covalent modification.
  • Reactivation studies using various thiol compounds.

Main Results:

  • Compound 1 irreversibly inactivates cystathionine γ-synthetase and methionine γ-lyase via mechanism-based inactivation.
  • Inactivation is covalent, stoichiometric, and exhibits saturation kinetics.
  • Enzymes can be reactivated by thiols, releasing p-nitrophenylthiolate.
  • Regioisomers of compound 1 do not show inactivation activity.

Conclusions:

  • A novel suicide inactivation mechanism involving β-carbanion-assisted elimination and sigmatropic rearrangement is proposed.
  • The inhibitor targets key enzymes in bacterial methionine metabolism.
  • This study provides insights into enzyme inhibition mechanisms and potential therapeutic strategies.