Water-Compatible Staudinger–Diels–Alder LigationClick to copy article linkArticle link copied!
- Masaru Tanioka*Masaru Tanioka*Email: [email protected]Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Masaru Tanioka
- Shohei KanayamaShohei KanayamaGraduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Shohei Kanayama
- Fumino KitamuraFumino KitamuraGraduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Fumino Kitamura
- Akinari TakanoAkinari TakanoGraduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Akinari Takano
- Yukiko IkedaYukiko IkedaGraduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Yukiko Ikeda
- Aki KohyamaAki KohyamaGraduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Aki Kohyama
- Tsuyoshi YamadaTsuyoshi YamadaGraduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Tsuyoshi Yamada
- Yuji Matsuya*Yuji Matsuya*Email: [email protected]Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanMore by Yuji Matsuya
Abstract

The development of bioorthogonal reactions is expected to propel further advances in chemical biology. In this study, we demonstrate Staudinger–Diels–Alder (SDA) ligation as a candidate for a new bioorthogonal reaction. This reaction ligates two molecules via strong C–C bonds at room temperature. We found that the aryl substituent of azide-benzocyclobutene (azide-BCB) had a strong influence on the molecule’s tolerance to water. In particular, Cl-substituted azide-BCBs generated the ligated product in high yield, even in the presence of water. Mechanistic investigations using DFT methods revealed that hydrophobic electron-withdrawing substituents suppressed the side reactions of SDA ligation.
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