Near-Quantitative Aqueous Synthesis of Rotaxanes via Bioconjugation to Oligopeptides and Proteins

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• 作者：Carson J. Bruns ; Hanwei Liu ; Matthew B. Francis
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：November 30, 2016
• 年：2016
• 卷：138
• 期：47
• 页码：15307-15310
• 全文大小：418K
• ISSN：1520-5126

文摘

In spite of widespread interest in rotaxane-based molecular machines and materials, rotaxanes have not been attached covalently to proteins. We describe the near-quantitative aqueous synthesis of [2]rotaxanes based on neutral and charged aqueous hosts—cucurbit[7]uril (CB7) and cyclobis(paraquat-p-phenylene) (CBPQT⁴⁺), respectively—using the thiol-ene addition of cysteine and maleimide as a stoppering protocol. After verifying the high efficiency of the reaction using glutathione (GSH) as an oligopeptide stopper, we have employed cytochrome C (CytC) as a protein stopper to produce the first well-characterized protein-rotaxane bioconjugates. We anticipate that this methodology will enable the preparation of novel materials that combine the unique properties of proteins and mechanical bonds.