原位生成喹嗪鎓，用于可见光诱导的金（III）催化炔化和多肽修饰

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-08-15 DOI:10.1002/ajoc.202400339

Wa-Yi O, Ajcharapan Tantipanjaporn, Jie-Ren Deng, Rui Tang, Karen Ka-Yan Kung, Hoi-Yi Sit, Chun-Him Nathanael Lai, Man-Kin Wong

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引用次数: 0

摘要

我们开发了一种新方法，即可见光诱导的金（III）催化的双重炔化作用及其在选择性修饰炔连接肽中的应用。双环金属化金（III）复合物具有双重作用：（1）原位生成喹嗪基光敏剂（λem = 500 - 594 nm）；（2）亚胺离子的炔化。在优化的条件下，炔化产物的产率高达 73%。在选择性修饰炔连接肽的过程中应用这种策略，修饰肽的转化率高达 67%。我们的可见光/金（III）双重催化技术体现了光催化与过渡金属催化相结合开发新型生物共轭的潜力。

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In Situ Generation of Quinoliziniums for Dual Visible Light-Induced Gold(III)-Catalyzed Alkynylation and Peptide Modification

A new approach of dual visible light-induced gold(III)-catalyzed alkynylation and its application in selective modification of alkyne-linked peptides has been developed. The bis-cyclometalated gold(III) complex exhibited dual roles of (1) in situ generation of quinolizinium-based photosensitizer (λ_em=500 – 594 nm) and (2) alkynylation of iminium ions. Under optimized conditions, alkynylated products were afforded in good yields up to 73 %. The application of this strategy in selective modification of alkyne-linked peptides gave modified peptides in up to 67 % conversion. Our dual visible light/gold(III) catalysis exemplifies the potential of merging photocatalysis and transition metal catalysis to develop novel bioconjugation.

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.