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

Chem Commun (Camb). 2023 Dec 7;59(98):14563-14566. doi: 10.1039/d3cc05015g.

Authors

Hiroyuki Yamakoshi¹, Daiki Shibata¹, Kazuki Bando^{2

3}, Shinji Kajimoto^{1

4}, Aki Kohyama¹, Syusuke Egoshi^{5

6}, Kosuke Dodo^{5

6}, Yoshiharu Iwabuchi¹, Mikiko Sodeoka^{5

6}, Katsumasa Fujita^{2

3

7}, Takakazu Nakabayashi¹

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan. [email protected].
² Department of Applied Physics, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
³ National Institute of Advanced Industrial Science and Technology (AIST), 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
⁴ JST PREST, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.
⁵ Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
⁶ Catalysis and Integrated Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
⁷ Institute for Open and Transdisciplinary Research Initiatives, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 37986604
DOI: 10.1039/d3cc05015g

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.