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 journalArticle

1 Citation (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 languageEnglish
Pages (from-to)753-755
Number of pages3
JournalChemistry Letters
Volume46
Issue number5
DOIs
Publication statusPublished - 2017

Fingerprint

Firefly Luciferin
Biosynthesis
Cysteine
Thiazoles
Nitriles
Biomimetics
Metals
Derivatives
Catalysts
Temperature

Keywords

  • Biomimetic coupling
  • Click chemistry
  • Firefly luciferin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Toyama, T., Saitoh, T., Takahashi, Y., Oka, K., Citterio, D., Suzuki, K., & Nishiyama, S. (2017). Click reaction based on the biosynthesis of firefly luciferin. Chemistry Letters, 46(5), 753-755. https://doi.org/10.1246/cl.170094

Click reaction based on the biosynthesis of firefly luciferin. / Toyama, Tomohisa; Saitoh, Tsuyoshi; Takahashi, Yuka; Oka, Kotaro; Citterio, Daniel; Suzuki, Koji; Nishiyama, Shigeru.

In: Chemistry Letters, Vol. 46, No. 5, 2017, p. 753-755.

Research output: Contribution to journalArticle

Toyama, T, Saitoh, T, Takahashi, Y, Oka, K, Citterio, D, Suzuki, K & Nishiyama, S 2017, 'Click reaction based on the biosynthesis of firefly luciferin', Chemistry Letters, vol. 46, no. 5, pp. 753-755. https://doi.org/10.1246/cl.170094
Toyama, Tomohisa ; Saitoh, Tsuyoshi ; Takahashi, Yuka ; Oka, Kotaro ; Citterio, Daniel ; Suzuki, Koji ; Nishiyama, Shigeru. / Click reaction based on the biosynthesis of firefly luciferin. In: Chemistry Letters. 2017 ; Vol. 46, No. 5. pp. 753-755.
@article{f43445a73a5e4b5aad08425003ac80c3,
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",
year = "2017",
doi = "10.1246/cl.170094",
language = "English",
volume = "46",
pages = "753--755",
journal = "Chemistry Letters",
issn = "0366-7022",
publisher = "Chemical Society of Japan",
number = "5",

}

TY - JOUR

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

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

UR - http://www.scopus.com/inward/record.url?scp=85028083783&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85028083783&partnerID=8YFLogxK

U2 - 10.1246/cl.170094

DO - 10.1246/cl.170094

M3 - Article

VL - 46

SP - 753

EP - 755

JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

IS - 5

ER -