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Title
Efficient low-cost preparation of trans-cyclooctenes using a simplified flow setup for photoisomerization
AuthorSvatunek, Dennis ; Denk, Christoph ; Rosecker, Veronika ; Sohr, Barbara ; Hametner, Christian In der Gemeinsamen Normdatei der DNB nachschlagen ; Allmaier, Günter ; Fröhlich, Johannes In der Gemeinsamen Normdatei der DNB nachschlagen ; Mikula, Hannes
Published in
Monatshefte für Chemie - Chemical Monthly, Vienna, 2016, Vol. 147, Issue 3, page 579-585
PublishedSpringer Vienna, 2016
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Published version
LanguageEnglish
Document typeJournal Article
Keywords (DE)Fotochemie / Cycloaddition / Click-Chemie / Alkene / Isomerisierung / Bioorthogonale Markierung
Keywords (EN)Photochemistry / Cycloadditions / Click chemistry / Alkenes / Isomerization / Bioorthogonal chemistry
ISSN1434-4475
URNurn:nbn:at:at-ubtuw:3-1465 Persistent Identifier (URN)
DOI10.1007/s00706-016-1668-z 
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 The work is publicly available
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Abstract (English)

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.

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CC-BY-License (4.0)Creative Commons Attribution 4.0 International License