Ratiometric analysis of reversible thia-Michael reactions using nitrile-tagged molecules by Raman microscopy

Hiroyuki Yamakoshi; Daiki Shibata; Kazuki Bando; Shinji Kajimoto; Aki Kohyama; Syusuke Egoshi; Kosuke Dodo; Yoshiharu Iwabuchi; Mikiko Sodeoka; Katsumasa Fujita; Takakazu Nakabayashi

doi:10.1039/D3CC05015G

Ratiometric analysis of reversible thia-Michael reactions using nitrile-tagged molecules by Raman microscopy†

Hiroyuki Yamakoshi,

*^a Daiki Shibata,

^a Kazuki Bando,

^bc Shinji Kajimoto,

^ad Aki Kohyama,

^a Syusuke Egoshi,

^ef Kosuke Dodo,

^ef Yoshiharu Iwabuchi,

^a Mikiko Sodeoka,

^ef Katsumasa Fujita

^bcg and Takakazu Nakabayashi

^a

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, Japan
E-mail: hiroyuki.yamakoshi.e1@tohoku.ac.jp

^b Department of Applied Physics, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

^c National Institute of Advanced Industrial Science and Technology (AIST), 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

^d JST PREST, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan

^e Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

^f Catalysis and Integrated Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

^g Institute for Open and Transdisciplinary Research Initiatives, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract

Ratiometric Raman analysis of reversible thia-Michael reactions was achieved using α-cyanoacrylic acid (αCNA) derivatives. Among αCNAs, the smallest derivative, ThioRas (molecular weight: 167 g mol⁻¹), and its glutathione adduct were simultaneously detected in various subcellular locations using Raman microscopy.

Chemical Communications

Ratiometric analysis of reversible thia-Michael reactions using nitrile-tagged molecules by Raman microscopy†

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Ratiometric analysis of reversible thia-Michael reactions using nitrile-tagged molecules by Raman microscopy

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