Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells

Tomohiro Meguro; Norikazu Terashima; Harumi Ito; Yuka Koike; Isao Kii; Suguru Yoshida; Takamitsu Hosoya

doi:10.1039/C8CC00179K

Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells†

Tomohiro Meguro,^a Norikazu Terashima,^a Harumi Ito,

^ab Yuka Koike,^c Isao Kii,

^bc Suguru Yoshida

*^a and Takamitsu Hosoya

*^ad

Author affiliations

* Corresponding authors

^a Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
E-mail: s-yoshida.cb@tmd.ac.jp, thosoya.cb@tmd.ac.jp

^b Pathophysiological and Health Science Team, Division of Bio-Function Dynamics Imaging, Imaging Platform and Innovation Group, RIKEN Center for Life Science Technologies (CLST), 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan

^c Common Facilities Unit, Compass to Healthy Life Research Complex Program, RIKEN Cluster for Science and Technology Hub, 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan

^d Chemical Biology Team, Division of Bio-Function Dynamic Imaging, RIKEN Center for Life Science Technologies (CLST), 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan

Abstract

Efficient formation of water- and air-stable aza-ylides has been achieved using the Staudinger reaction between electron-deficient aromatic azides such as 2,6-dichlorophenyl azide and triarylphosphines. The reaction proceeds rapidly and has been successfully applied to chemical modification of proteins in living cells.

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Article information

DOI: https://doi.org/10.1039/C8CC00179K
Article type: Communication
Submitted: 09 Jan 2018
Accepted: 13 May 2018
First published: 14 May 2018
This article is Open Access

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Chem. Commun., 2018,54, 7904-7907

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Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells

T. Meguro, N. Terashima, H. Ito, Y. Koike, I. Kii, S. Yoshida and T. Hosoya, Chem. Commun., 2018, 54, 7904 DOI: 10.1039/C8CC00179K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Communications

Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells†

Abstract

Supplementary files

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Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells

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