Related Experiment Video
Updated: Jul 7, 2025
12:31
Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
24.5K
Copper-Catalyzed Azide-Alkyne Cycloaddition-Oriented Multifunctional Bio-Orthogonal Linker BPPA: Design, Synthesis
Shuo Wang1, Xu He1, Junchen Li1
1State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China.
Molecules (Basel, Switzerland)
|December 23, 2023
Summary
Researchers developed novel biotin-based tetra-functional bio-orthogonal linkers (BPPA) for proteomic target profiling. These linkers feature a photolabile group and dual click chemistry options, enabling efficient protein labeling and analysis.
Area of Science:
- Organic Chemistry
- Chemical Biology
- Proteomics
Background:
- Bio-orthogonal reactions are essential for studying complex biological systems.
- Developing versatile linker molecules is key for advanced proteomic target profiling.
Purpose of the Study:
- To synthesize and characterize novel biotin-based tetra-functional bio-orthogonal linkers (BPPA).
- To evaluate the utility of these linkers in bio-orthogonal reactions, specifically copper-catalyzed azide-alkyne cycloaddition (CuAAC).
Main Methods:
- A green, one-step synthesis of BPPA linkers from biotin acids and functionalized acetophenones.
- Copper-catalyzed azide-alkyne cycloaddition (CuAAC) for linking BPPA to target molecules.
- Evaluation of linker cleavage via UV irradiation and ammonia hydrolysis.
Main Results:
- BPPA linkers were synthesized in high yields (85-90%).
- CuAAC reactions proceeded efficiently, yielding BPPA-triazole adducts in nearly quantitative yields.
- The photolabile phenacyl ester motif allowed for efficient C-O bond cleavage under UV irradiation or ammonia hydrolysis.
Conclusions:
- The novel BPPA linkers offer dual click chemistry capabilities (azide or alkyne).
- These linkers are suitable for CuAAC-oriented bio-orthogonal reactions in proteomics.
- The photolabile nature and efficient cleavage facilitate controlled release of protein-bound fragments.
More Related Videos
Related Concept Videos
01:16Cycloaddition Reactions: Overview
2.6K
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.
2.6K
01:16Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
2.6K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
2.6K