Chang, Chia-Hao;
Gómez, Sandra;
Fontaine, Danielle M;
Fikas, Panagiotis;
Branchini, Bruce R;
Anderson, James C;
(2023)
Bioluminescence, photophysical, computational and molecular docking studies of fully conformationally restricted enamine infraluciferin.
Organic & Biomolecular Chemistry
10.1039/d3ob00247k.
(In press).
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Abstract
A new rationally designed fully rotationally restricted luciferin has been synthesised. This synthetic luciferin, based upon the structure of infraluciferin, has two intramolecular H-bonds to reduce degrees of freedom, an amine group to enhance ICT process, and an alkenyl group to increase π-conjugation. In the spectroscopic measurements and computational calculations, enamine luciferin showed more red-shifted absorption and fluorescence emission than LH2 and iLH2. With PpyWT luciferase enamine luciferin gave bioluminescence at 564 nm which is similar to LH2 at 561 nm. Further investigation by docking studies revealed that the emission wavelength of enamine luciferin might be attributed to the unwanted twisted structure caused by Asp531 within the enzyme. With mutant luciferase FlucRed, the major emission peak was shifted to 606 nm, a distinct shoulder above 700 nm, and 21% of its spectrum located in the nIR range.
| Type: | Article |
|---|---|
| Title: | Bioluminescence, photophysical, computational and molecular docking studies of fully conformationally restricted enamine infraluciferin |
| Location: | England |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/d3ob00247k |
| Publisher version: | https://doi.org/10.1039/D3OB00247K |
| Language: | English |
| Additional information: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery-pp.ucl.ac.uk/id/eprint/10167067 |
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