Related Experiment Video
Updated: Mar 26, 2026
07:11
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
3.2K
Allene Functionalized Azobenzene Linker Enables Rapid and Light-Responsive Peptide Macrocyclization.
Mohammad R Jafari1, Jenner Lakusta1, Rylan J Lundgren1
1Department of Chemistry and ‡Alberta Glycomics Centre, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
Bioconjugate Chemistry
|February 6, 2016
Summary
Researchers developed a new water-soluble azobenzene reagent for fast, visible light-triggered peptide modifications. This tool enables rapid creation of light-responsive macrocyclic peptides and peptide libraries on bacteriophage surfaces.
Area of Science:
- Organic Chemistry
- Biochemistry
- Molecular Biology
Background:
- Azobenzene derivatives are widely used as photo-responsive molecules.
- Macrocyclic peptides offer unique structural and functional properties.
- Bacteriophage display is a powerful technique for peptide library screening.
Purpose of the Study:
- To synthesize a novel bis(allenamide) functionalized water-soluble azobenzene reagent (BSBDA).
- To demonstrate the utility of BSBDA for rapid visible light-responsive peptide modifications.
- To apply BSBDA for generating macrocyclic peptide libraries on bacteriophage surfaces.
Main Methods:
- Efficient synthesis of the BSBDA reagent.
- Cysteine ligation reactions with model peptides and phage-displayed peptides.
- Characterization of the photo-responsive properties of modified peptides.
Main Results:
- BSBDA was synthesized efficiently and is water-soluble.
- The allenamide functionality in BSBDA promotes rapid cysteine ligation.
- Ligation rates mediated by BSBDA are 2-3 orders of magnitude faster than traditional methods.
- Visible light-responsive macrocyclic peptides and libraries were successfully generated on bacteriophage.
Conclusions:
- BSBDA is a novel and efficient reagent for photo-responsive peptide chemistry.
- The rapid cysteine ligation capability of BSBDA significantly advances peptide modification techniques.
- BSBDA provides a new tool for creating light-switchable peptide systems and libraries for various applications.
Related Concept Videos
00:53Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
2.3K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.3K
01:12Cycloaddition Reactions: MO Requirements for Photochemical Activation
2.9K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.9K
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
4.0K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
4.0K
02:35Free-Radical Chain Reaction and Polymerization of Alkenes
10.2K
The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
10.2K
02:27Preparation of Alkynes: Alkylation Reaction
12.6K
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.
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.
12.6K
01:22Preparation of 1° Amines: Azide Synthesis
4.8K
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...
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...
4.8K