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Related Concept Videos

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

2.6K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
2.6K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.3K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

9.0K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
9.0K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

29.7K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
29.7K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.2K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.2K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

6.9K
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...
6.9K

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Protein stapling via azide-alkyne ligation.

Diya M Abdeljabbar1, Frank J Piscotta, Siyan Zhang

  • 1Department of Chemical and Biological Engineering, Princeton University, Princeton, NJ 08544, USA. ajlink@princeton.edu.

Chemical Communications (Cambridge, England)
|October 18, 2014
PubMed
Summary

Protein stapling introduces covalent constraints into proteins using click chemistry. This method enhances protein thermostability and improves protein G binding affinity to immunoglobulin G.

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Area of Science:

  • Biochemistry
  • Protein Engineering
  • Chemical Biology

Background:

  • Recombinant proteins are crucial in biotechnology and therapeutics.
  • Enhancing protein stability and function is a key challenge in protein engineering.

Purpose of the Study:

  • To develop a novel methodology, protein stapling, for introducing covalent constraints into recombinant proteins.
  • To evaluate the impact of protein stapling on protein thermostability and binding affinity.

Main Methods:

  • Utilized azide-alkyne click reaction for protein stapling.
  • Applied the methodology to a model leucine zipper protein to assess thermostability.
  • Investigated the effect of stapling on the binding of protein G to immunoglobulin G.

Main Results:

  • Successfully demonstrated protein stapling methodology for creating covalent constraints.
  • Achieved improved thermostability in a model leucine zipper protein.
  • Observed enhanced binding affinity of protein G to immunoglobulin G after core stapling.

Conclusions:

  • Protein stapling is an effective strategy for enhancing protein properties.
  • The developed methodology offers a versatile tool for protein engineering applications.
  • This approach holds potential for improving the stability and functionality of therapeutic proteins.