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Utilization of a Branched Late-Stage Clickable Biotinylated Chassis on the Example of a Pittsburgh B Analogue
Organic Letters ( IF 4.9 ) Pub Date : 2024-07-25 , DOI: 10.1021/acs.orglett.4c02527
T. Moritz Weber 1 , Pelin Özdüzenciler 2, 3 , Gültekin Tamgüney 2, 3 , Jörg Pietruszka 1, 4
Affiliation  

Biotinylation is probably the most frequent and practically useful modification of molecules to facilitate selective and highly affine binding to (strept)avidin for immobilization, enrichment, and purification for further (bio)chemical or (bio)physical investigations. We present a protecting-group-free synthesis of a branched biotin bis-azide that enables dual-payload late-stage functionalization with arbitrary alkynes via click chemistry. Utility of the chassis is briefly showcased on the example of a valuable Pittsburgh B analogue, which binds pathological protein aggregates, commonly found in neurodegenerative diseases.

中文翻译:


以匹兹堡 B 类似物为例,利用分支后期可点击生物素化底盘



生物素化可能是最常见且实用的分子修饰,以促进与(链霉)抗生物素蛋白的选择性和高度亲和性结合,以进行固定、富集和纯化,以进行进一步的(生物)化学或(生物)物理研究。我们提出了一种无保护基团的支链生物素双叠氮化物合成方法,可通过点击化学使用任意炔烃进行双有效负载后期功能化。以有价值的 Pittsburgh B 类似物为例简要展示了底盘的实用性,该类似物可结合神经退行性疾病中常见的病理性蛋白质聚集体。
更新日期:2024-07-26
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