Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution

Nobuo Kitada; Tsuyoshi Saitoh; Yuma Ikeda; Satoshi Iwano; Rika Obata; Haruki Niwa; Takashi Hirano; Atsushi Miyawaki; Koji Suzuki; Shigeru Nishiyama; Shojiro A. Maki

doi:10.1016/j.tetlet.2018.01.078

Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution

Nobuo Kitada, Tsuyoshi Saitoh, Yuma Ikeda, Satoshi Iwano, Rika Obata, Haruki Niwa, Takashi Hirano, Atsushi Miyawaki, Koji Suzuki, Shigeru Nishiyama, Shojiro A. Maki

Department of Humanities and Social Sciences

Research output: Contribution to journal › Article

6 Citations (Scopus)

Abstract

The synthesis and bioluminescence of allyl-substituted luciferin derivatives as substrates for firefly luciferase are reported. The allylation of luciferins induced bathochromic shift (15–40 nm) of the bioluminescence emission. Upon combination with other chemical modifications for bioluminescence wavelength tuning, novel red emitting luciferin analogues were obtained with emission maxima at 685 and 690 nm.

Original language	English
Pages (from-to)	1087-1090
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2018.01.078
Publication status	Published - 2018 Mar 21

Keywords

Bioluminescence
Firefly
Luciferin derivatives
Near infrared

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Kitada, N., Saitoh, T., Ikeda, Y., Iwano, S., Obata, R., Niwa, H., Hirano, T., Miyawaki, A., Suzuki, K., Nishiyama, S., & Maki, S. A. (2018). Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution. Tetrahedron Letters, 59(12), 1087-1090. https://doi.org/10.1016/j.tetlet.2018.01.078

Toward bioluminescence in the near-infrared region : Tuning the emission wavelength of firefly luciferin analogues by allyl substitution. / Kitada, Nobuo; Saitoh, Tsuyoshi; Ikeda, Yuma; Iwano, Satoshi; Obata, Rika; Niwa, Haruki; Hirano, Takashi; Miyawaki, Atsushi; Suzuki, Koji; Nishiyama, Shigeru; Maki, Shojiro A.

In: Tetrahedron Letters, Vol. 59, No. 12, 21.03.2018, p. 1087-1090.

Research output: Contribution to journal › Article

Kitada, Nobuo ; Saitoh, Tsuyoshi ; Ikeda, Yuma ; Iwano, Satoshi ; Obata, Rika ; Niwa, Haruki ; Hirano, Takashi ; Miyawaki, Atsushi ; Suzuki, Koji ; Nishiyama, Shigeru ; Maki, Shojiro A. / Toward bioluminescence in the near-infrared region : Tuning the emission wavelength of firefly luciferin analogues by allyl substitution. In: Tetrahedron Letters. 2018 ; Vol. 59, No. 12. pp. 1087-1090.

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abstract = "The synthesis and bioluminescence of allyl-substituted luciferin derivatives as substrates for firefly luciferase are reported. The allylation of luciferins induced bathochromic shift (15–40 nm) of the bioluminescence emission. Upon combination with other chemical modifications for bioluminescence wavelength tuning, novel red emitting luciferin analogues were obtained with emission maxima at 685 and 690 nm.",

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AU - Ikeda, Yuma

AU - Iwano, Satoshi

AU - Obata, Rika

AU - Niwa, Haruki

AU - Hirano, Takashi

AU - Miyawaki, Atsushi

AU - Suzuki, Koji

AU - Nishiyama, Shigeru

AU - Maki, Shojiro A.

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KW - Luciferin derivatives

KW - Near infrared

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