A facile preparation of functional cycloalkynes via an azide-to-cycloalkyne switching approach

Suguru Yoshida; Tomoko Kuribara; Harumi Ito; Tomohiro Meguro; Yoshitake Nishiyama; Fumika Karaki; Yasutomo Hatakeyama; Yuka Koike; Isao Kii; Takamitsu Hosoya

doi:10.1039/C9CC01113G

A facile preparation of functional cycloalkynes via an azide-to-cycloalkyne switching approach†

Suguru Yoshida,

*^a Tomoko Kuribara,^a Harumi Ito,

^ab Tomohiro Meguro,^a Yoshitake Nishiyama,^a Fumika Karaki,

‡^a Yasutomo Hatakeyama,^a Yuka Koike,^c Isao Kii

^bc and Takamitsu Hosoya

*^ad

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* 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 Laboratory for Pathophysiological and Health Science, RIKEN Center for Biosystems Dynamics Research (BDR), 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, Technology and Innovation Hub, 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan

^d Laboratory for Chemical Biology, RIKEN Center for Biosystems Dynamics Research (BDR), 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan

Abstract

A facile method for preparing various functional cycloalkynes, including proteins incorporated with a cycloalkyne moiety, from the corresponding azides is developed. Treatment of diynes bearing strained and terminal alkyne moieties with a copper salt enabled terminal alkyne-selective click conjugation with azides, whereas a more azidophilic strained alkyne moiety was transiently protected from the click reaction via complexation with copper.

Chemical Communications

A facile preparation of functional cycloalkynes via an azide-to-cycloalkyne switching approach†

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A facile preparation of functional cycloalkynes via an azide-to-cycloalkyne switching approach

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