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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title = "Click reaction based on the biosynthesis of firefly luciferin",

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.",

keywords = "Biomimetic coupling, Click chemistry, Firefly luciferin",

author = "Tomohisa Toyama and Tsuyoshi Saitoh and Yuka Takahashi and Kotaro Oka and Daniel Citterio and Koji Suzuki and Shigeru Nishiyama",

note = "Funding Information: We are grateful for financial support from The Japan Society for the Promotion of Science (JSPS). This work was partially supported by JSPS KAKENHI Grant Number 24225001. Publisher Copyright: {\textcopyright} 2017 The Chemical Society of Japan.",

year = "2017",

doi = "10.1246/cl.170094",

language = "English",

volume = "46",

pages = "753--755",

journal = "Chemistry Letters",

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publisher = "Chemical Society of Japan",

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T1 - Click reaction based on the biosynthesis of firefly luciferin

AU - Toyama, Tomohisa

AU - Saitoh, Tsuyoshi

AU - Takahashi, Yuka

AU - Oka, Kotaro

AU - Citterio, Daniel

AU - Suzuki, Koji

AU - Nishiyama, Shigeru

N1 - Funding Information: We are grateful for financial support from The Japan Society for the Promotion of Science (JSPS). This work was partially supported by JSPS KAKENHI Grant Number 24225001. Publisher Copyright: © 2017 The Chemical Society of Japan.

PY - 2017

Y1 - 2017

N2 - 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.

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

KW - Firefly luciferin

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JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

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Click reaction based on the biosynthesis of firefly luciferin

Abstract

Keywords

ASJC Scopus subject areas

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