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Related Concept Videos

Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.2K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.2K
Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

4.6K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
4.6K
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation01:14

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

7.1K
This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.
7.1K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.0K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.0K
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

24.0K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
24.0K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

3.3K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
3.3K

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Related Experiment Video

Updated: Feb 4, 2026

Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry
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A novel lipase-catalyzed method for preparing ELR-based bioconjugates.

Ana M Testera1, Mercedes Santos1, Alessandra Girotti1

  • 1BIOFORGE (Group for Advanced Materials and Nanobiotechnology) - CIBER-BBN, University of Valladolid, Valladolid, Spain.

International Journal of Biological Macromolecules
|October 13, 2018
PubMed
Summary

This study introduces a new enzymatic method to modify elastin-like recombinamers (ELRs) for advanced biomaterials. These functionalized ELRs offer new possibilities for stimuli-responsive drug delivery systems.

Keywords:
Amidation reactionCAL-B lipaseControlled drug deliveryElastin-like recombinamersEnzymatic modificationPolymer bioconjugation

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Biotechnology

Background:

  • Elastin-like recombinamers (ELRs) are versatile biopolymers with potential in regenerative medicine.
  • Modifying ELRs with specific functionalities can enhance their application in advanced biomaterials.
  • Stimuli-responsive materials are crucial for controlled drug delivery systems.

Purpose of the Study:

  • To develop a novel, mild, and efficient one-pot method for the chemical modification of ELRs.
  • To introduce diverse functionalities into ELRs for applications in regenerative medicine and controlled drug delivery.
  • To create ELRs responsive to stimuli beyond pH and temperature, such as glucose concentration and electromagnetic radiation.

Main Methods:

  • Enzymatic catalysis using Candida antarctica lipase B (Novozym 435) for amidation reactions.
  • Chemical modification of ELRs containing carboxylic groups with aminated substrates.
  • Kinetic studies of the amidation reaction under various conditions using a model phenylazobenzene derivative.
  • Coupling of phenylboronic acid (FB-NH2) and polyethylene glycol (PEG-NH2) to obtain functionalized ELRs.

Main Results:

  • Successful one-pot chemical modification of ELRs under mild and efficient enzymatic conditions.
  • Obtained photoresponsive, glucose-responsive, and PEGylated ELRs.
  • Demonstrated the feasibility of introducing specific functionalities for tailored biomaterial properties.
  • Optimized amidation reaction conditions for efficient substrate coupling.

Conclusions:

  • The novel enzymatic method provides a versatile platform for creating functionalized ELRs.
  • These modified ELRs hold significant potential for developing advanced biomaterials, particularly for stimuli-responsive drug delivery devices and sensors.
  • The ability to tune ELR responsiveness expands their utility in regenerative medicine and beyond.