Click reaction based on the biosynthesis of firefly luciferin

Tomohisa Toyama; Tsuyoshi Saitoh; Yuka Takahashi; Kotaro Oka; Daniel Citterio; Koji Suzuki; Shigeru Nishiyama

doi:10.1246/cl.170094

Click reaction based on the biosynthesis of firefly luciferin

Tomohisa Toyama, Tsuyoshi Saitoh, Yuka Takahashi, Kotaro Oka, Daniel Citterio, Koji Suzuki, Shigeru Nishiyama

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Novel click chemistry was developed based on the biosynthetic process of firefly luciferin, which includes an ideal coupling of a cyanothiazole residue with cysteine. Among various biomimetic couplings of nitriles with cysteine derivatives, the approach using 4-cyanopyridine and cysteine methyl ester provided a very rapid and quantitative conversion to the corresponding thiazole without any metal catalyst at room temperature.

Original language	English
Pages (from-to)	753-755
Number of pages	3
Journal	Chemistry Letters
Volume	46
Issue number	5
DOIs	https://doi.org/10.1246/cl.170094
Publication status	Published - 2017

Keywords

Biomimetic coupling
Click chemistry
Firefly luciferin

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.170094

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AU - Toyama, Tomohisa

AU - Saitoh, Tsuyoshi

AU - Takahashi, Yuka

AU - Oka, Kotaro

AU - Citterio, Daniel

AU - Suzuki, Koji

AU - Nishiyama, Shigeru

PY - 2017

Y1 - 2017

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AB - Novel click chemistry was developed based on the biosynthetic process of firefly luciferin, which includes an ideal coupling of a cyanothiazole residue with cysteine. Among various biomimetic couplings of nitriles with cysteine derivatives, the approach using 4-cyanopyridine and cysteine methyl ester provided a very rapid and quantitative conversion to the corresponding thiazole without any metal catalyst at room temperature.

KW - Biomimetic coupling

KW - Click chemistry

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