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

Research output: Contribution to journal › Article

4 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 languageEnglish
Pages (from-to)1087-1090
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number12
DOIs
Publication statusPublished - 2018 Mar 21

Fingerprint

Firefly Luciferin
Bioluminescence
Firefly Luciferases
Substitution reactions
Tuning
Infrared radiation
Wavelength
Allylation
Chemical modification
Derivatives
Substrates

Keywords

  • Bioluminescence
  • Firefly
  • Luciferin derivatives
  • Near infrared

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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, N, Saitoh, T, Ikeda, Y, Iwano, S, Obata, R, Niwa, H, Hirano, T, Miyawaki, A, Suzuki, K, Nishiyama, S & Maki, SA 2018, 'Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution', Tetrahedron Letters, vol. 59, no. 12, pp. 1087-1090. https://doi.org/10.1016/j.tetlet.2018.01.078
Kitada N, Saitoh T, Ikeda Y, Iwano S, Obata R, Niwa H et al. Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution. Tetrahedron Letters. 2018 Mar 21;59(12):1087-1090. https://doi.org/10.1016/j.tetlet.2018.01.078
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.
@article{1226108a83c94eef9cc67ccfe3adafd5,
title = "Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution",
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.",
keywords = "Bioluminescence, Firefly, Luciferin derivatives, Near infrared",
author = "Nobuo Kitada and Tsuyoshi Saitoh and Yuma Ikeda and Satoshi Iwano and Rika Obata and Haruki Niwa and Takashi Hirano and Atsushi Miyawaki and Koji Suzuki and Shigeru Nishiyama and Maki, {Shojiro A.}",
year = "2018",
month = "3",
day = "21",
doi = "10.1016/j.tetlet.2018.01.078",
language = "English",
volume = "59",
pages = "1087--1090",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

T1 - Toward bioluminescence in the near-infrared region

T2 - Tuning the emission wavelength of firefly luciferin analogues by allyl substitution

AU - Kitada, Nobuo

AU - Saitoh, Tsuyoshi

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.

PY - 2018/3/21

Y1 - 2018/3/21

N2 - 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.

AB - 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.

KW - Bioluminescence

KW - Firefly

KW - Luciferin derivatives

KW - Near infrared

UR - http://www.scopus.com/inward/record.url?scp=85042165522&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042165522&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.01.078

DO - 10.1016/j.tetlet.2018.01.078

M3 - Article

AN - SCOPUS:85042165522

VL - 59

SP - 1087

EP - 1090

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 12

ER -

Access to Document