多芳香族配位胶囊与线性单萜的生物结合和转化

IF 3.3 Q2 CHEMISTRY, MULTIDISCIPLINARY
Ryuki Sumida, Lorenzo Catti and Michito Yoshizawa*, 
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引用次数: 0

摘要

线性单萜烯是多功能的反应生物底物,只有在天然酶中才能以出色的选择性和效率与之结合并随后转化为各种环状单体和低聚物。我们在此报告合成聚芳香族空腔在溶液和固体状态下对线性单萜烯的生物启发功能。这些空腔由 Pt(II) 离子和弯曲的双吡啶配体与两个蒽面板组装形成的多芳香配位胶囊提供。通过使用胶囊空腔,证明了香茅醛与其他单萜混合物的选择性结合,以及香茅醛在水和固体状态下对其衍生物的优先气相结合。此外,该胶囊还能从香茅醛在水中经酸催化环化得到的反应混合物中提取对孟烷-3,8-二醇,并具有很高的产物选择性和立体选择性。得益于内部和外部的多芳香族空腔,气化香茅醛的催化环化二聚化反应可在装有酸的胶囊固体中高效进行,并在环境条件下生成/立体选择性地生成对孟烷-3,8-二醇香茅醛缩醛(基于胶囊的产率为 330%)。固体胶囊反应器可重复使用至少 5 次,并提高了转化率。本研究为通过合成多芳香族空腔模拟萜烯的生物合成开辟了一条新途径。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Bioinspired Binding and Conversion of Linear Monoterpenes by Polyaromatic Coordination Capsules

Bioinspired Binding and Conversion of Linear Monoterpenes by Polyaromatic Coordination Capsules

Linear monoterpenes, versatile reaction biosubstrates, are bound and subsequently converted to various cyclic monomers and oligomers with excellent selectivity and efficiency, only in natural enzymes. We herein report bioinspired functions of synthetic polyaromatic cavities toward linear monoterpenes in the solution and solid states. The cavities are provided by polyaromatic coordination capsules, formed by the assembly of Pt(II) ions and bent bispyridine ligands with two anthracene panels. By using the capsule cavities, the selective binding of citronellal from mixtures with other monoterpenes and its preferential vapor binding over its derivatives are demonstrated in water and in the solid state, respectively. The capsule furthermore extracts p-menthane-3,8-diol, with high product- and stereoselectivity, from a reaction mixture obtained by the acid-catalyzed cyclization of citronellal in water. Thanks to the inner and outer polyaromatic cavities, the catalytic cyclization-dimerization of vaporized citronellal efficiently proceeds in the acid-loaded capsule solid and product/stereoselectively affords p-menthane-3,8-diol citronellal acetal (∼330% yield based on the capsule) under ambient conditions. The solid capsule reactor can be reused at least 5 times with enhanced conversion. The present study opens up a new approach toward mimicking terpene biosynthesis via synthetic polyaromatic cavities.

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来源期刊
ACS Organic & Inorganic Au
ACS Organic & Inorganic Au 有机化学、无机化学-
CiteScore
4.10
自引率
0.00%
发文量
0
期刊介绍: ACS Organic & Inorganic Au is an open access journal that publishes original experimental and theoretical/computational studies on organic organometallic inorganic crystal growth and engineering and organic process chemistry. Short letters comprehensive articles reviews and perspectives are welcome on topics that include:Organic chemistry Organometallic chemistry Inorganic Chemistry and Organic Process Chemistry.
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