Efficient low-cost preparation of trans-cyclooctenes using a simplified flow setup for photoisomerization.
Efficient low-cost preparation of trans-cyclooctenes using a simplified flow setup for photoisomerization.
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DOI：
10.1007/s00706-016-1668-z
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发表时间：
2016
影响因子：
1.8
通讯作者：
Mikula H
中科院分区：
文献类型：
--
作者：
Svatunek D;Denk C;Rosecker V;Sohr B;Hametner C;Allmaier G;Fröhlich J;Mikula H
生物正交连接已经成为生物医学研究的高度通用的化学工具。1，2，4，5-四嗪与反式环辛烯(TCO)之间的超快反应，也称为四嗪连接，在这方面经常被使用。越来越多的四嗪结扎应用导致了对TCO化合物的需求增加，其商业供应仍然非常有限。已报道的利用流动化学制备TCO的光化学方法简单，产率高，但需要昂贵的设备。在这一贡献中，我们介绍了一种由容易获得的组件组装的低成本流动光反应器的构造和表征。利用所描述的体系成功地合成了所有常用的反式环辛烯衍生物。我们相信，所提出的光异构化体系将促进获得具有生物正交性的TCO衍生物。本文的在线版本(doi：10.1007/s00706-0161668-z)包含补充材料，授权用户可以使用。
Bioorthogonal ligations have emerged as highly versatile chemical tools for biomedical research. The exceptionally fast reaction between 1,2,4,5-tetrazines and trans-cyclooctenes (TCOs), also known as tetrazine ligation, is frequently used in this regard. Growing numbers of applications for the tetrazine ligation led to an increased demand for TCO compounds, whose commercial availability is still very limited. Reported photochemical procedures for the preparation of TCOs using flow chemistry are straightforward and high yielding but require expensive equipment. Within this contribution, we present the construction and characterization of a low-cost flow photoreactor assembled from readily accessible components. Syntheses of all commonly used trans-cyclooctene derivatives were successfully carried out using the described system. We are convinced that the presented system for photoisomerization will promote access to bioorthogonally reactive TCO derivatives. The online version of this article (doi:10.1007/s00706-016-1668-z) contains supplementary material, which is available to authorized users.