Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution. Issue 12 (21st March 2018)

• Record Type: Journal Article
• Authors: Kitada, Nobuo; Saitoh, Tsuyoshi; Ikeda, Yuma; Iwano, Satoshi; Obata, Rika; Niwa, Haruki; Hirano, Takashi; Miyawaki, Atsushi; Suzuki, Koji; Nishiyama, Shigeru; Maki, Shojiro A.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 12(2018)
• Page Start: 1087
• Page End: 1090
• Publication Date: 2018-03-21
• Subjects: Luciferin derivatives -- Bioluminescence -- Near infrared -- Firefly; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.01.078
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Allyl-substituted luciferin derivatives were designed and synthesized. Bioluminescence properties of allyl luciferin derivatives were evaluated. The allylation of luciferins induced bathochromic shift of their bioluminescence. The longest near-infrared bioluminescence emission wavelength was achieved. 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.