7-Hydroxy- N-Methylquinolinium Chromophore: A Photolabile Protecting Group for Blue-Light Uncaging

Tetsuo Narumi; Koichi Miyata; Akitaka Nii; Kohei Sato; Nobuyuki Mase; Toshiaki Furuta

doi:10.1021/acs.orglett.8b01505

7-Hydroxy- N-Methylquinolinium Chromophore: A Photolabile Protecting Group for Blue-Light Uncaging

Org Lett. 2018 Jul 20;20(14):4178-4182. doi: 10.1021/acs.orglett.8b01505. Epub 2018 Jun 29.

Authors

Tetsuo Narumi^{1

2}, Koichi Miyata¹, Akitaka Nii¹, Kohei Sato¹, Nobuyuki Mase^{1

3}, Toshiaki Furuta⁴

Affiliations

¹ Course of Applied Chemistry and Biochemical Engineering, Department of Engineering, Graduate School of Integrated Science and Technology , Shizuoka University , 3-5-1 Johoku , Hamamatsu , Shizuoka 432-8561 , Japan.
² Green Chemistry Research Division, Research Institute of Green Science and Technology , Shizuoka University , Hamamatsu , Shizuoka 432-8561 , Japan.
³ Green Energy Research Division, Research Institute of Green Science and Technology , Shizuoka University , Hamamatsu , Shizuoka 432-8561 , Japan.
⁴ Department of Biomolecular Science , Toho University , Funabashi, Chiba 274-8510 , Japan.

PMID: 29957954
DOI: 10.1021/acs.orglett.8b01505

Abstract

The development of the N-methyl-7-hydroxymethylquinolinium ( N-Me-7-HQm) caging chromophore as a novel visible-light-sensitive photolabile protecting group is described. N-Me-7-HQm-caged compounds can be photoactivated by blue-light-emitting diode (LED) light (458 nm) with high photolytic efficiency, supporting applications to caging chemistry, and they also have sufficient water solubility and high resistance to spontaneous hydrolysis.

Publication types

Research Support, Non-U.S. Gov't