Protocol for the synthesis of N-Alkyl bromomaleimide linkers
Jessica T. Mhlongo, Anamika Sharma, Fernando Albericio, Beatriz G. de la Torre
TL;DR
The paper presents a reliable method to synthesize bromomaleimide linkers with different chain lengths for use in molecular modification.
Contribution
A new synthetic protocol for bromomaleimides with varied chain lengths and bifunctional potential is introduced.
Findings
The method produces high-purity bromomaleimides in good to excellent yields.
Compound 5's bifunctional structure allows for dual payload conjugation.
Bromomaleimides show greater stability and selectivity for Cysteine modification compared to maleimides.
Abstract
Herein a straightforward and efficient method for synthesizing bromomaleimides with varied carbon chain lengths to modulate molecular properties has been reported. Compounds 1–4 incorporate a single bromomaleimide unit, while compound 5 features two, enabling dual functionalization. This synthetic approach consistently yields high-purity products in good to excellent yields, with compound 5 offering potential for dual payload conjugation due to its bifunctional structure. The key highlights are: 1. Bromomaleimides offers exceptional stability compared to maleimides counterparts 2. Highly selective for Cysteine modification Image, graphical abstract
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Taxonomy
TopicsCatalytic Cross-Coupling Reactions · Synthesis and Reactivity of Heterocycles · Chemical Synthesis and Analysis