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Related Concept Videos

Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

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Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...
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Esters to β-Ketoesters: Claisen Condensation Overview01:24

Esters to β-Ketoesters: Claisen Condensation Overview

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Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

4.0K
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:
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Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

4.8K
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
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Related Experiment Video

Updated: Feb 3, 2026

Injection of Hydrogel Biomaterial Scaffolds to The Brain After Stroke
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Versatile Hyperbranched Poly(β-hydrazide ester) Macromers as Injectable Antioxidative Hydrogels.

Qian Xu1, Manon Venet2, Wei Wang3

  • 1Charles Institute of Dermatology, School of Medicine , University College Dublin , Belfield, Dublin 4 , Ireland.

ACS Applied Materials & Interfaces
|October 31, 2018
PubMed
Summary

New synthetic biomaterials called hyperbranched poly(β-hydrazide ester)s (HB-PBHEs) can form hydrogels that degrade in response to reactive oxygen species (ROS). These ROS-responsive hydrogels protect cells in hostile microenvironments.

Keywords:
antioxidanthydrogelinjectablepoly(β-hydrazide ester)tissue engineering

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Fabricating Degradable Thermoresponsive Hydrogels on Multiple Length Scales via Reactive Extrusion, Microfluidics, Self-assembly, and Electrospinning
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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Biomedical Engineering

Background:

  • Reactive oxygen species (ROS) play a critical role in various pathologies, creating hostile microenvironments.
  • Developing ROS-responsive biomaterials is crucial for regulating these pathologies and improving cellular conditions.

Purpose of the Study:

  • To synthesize novel hyperbranched poly(β-hydrazide ester) macromers (HB-PBHEs) with disulfide moieties.
  • To investigate the gelation properties and ROS-responsive degradation of these HB-PBHEs.
  • To evaluate the cytoprotective effects of the resulting hydrogels in a high ROS environment.

Main Methods:

  • Synthesis of HB-PBHEs using an "A2 + B4" Michael addition approach.
  • Formation of injectable hydrogels via cross-linking with thiolated hyaluronic acid.
  • Formation of UV-cross-linked hydrogels.
  • Assessment of H2O2-responsive degradation.
  • Evaluation of cell viability under oxidative stress.

Main Results:

  • Successfully synthesized HB-PBHEs with disulfide moieties and multiacrylate end groups.
  • Achieved rapid gelation to form both injectable and UV-cross-linked hydrogels.
  • Demonstrated H2O2-responsive degradation of disulfide-containing macromers and hydrogels.
  • Confirmed that disulfide-containing hydrogels effectively maintain cell viability in high ROS conditions.

Conclusions:

  • The synthesized HB-PBHEs offer versatile gelation capabilities for creating ROS-responsive hydrogels.
  • Disulfide moieties enable controlled degradation in response to H2O2, a key ROS indicator.
  • These novel biomaterials show significant potential for protecting cells and mitigating ROS-induced pathologies.