Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases

Eveline Brodl, Jakov Ivkovic, Chaitanya Tabib, Rolf Breinbauer, Peter Macheroux

Research output: Contribution to journalArticle

Abstract

Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490 nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having a
double bond at the a,b-position. These a,b-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decay
rate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.
LanguageEnglish
Pages1487-1495
JournalBioorganic & medicinal chemistry
Volume25
Issue number4
StatusPublished - 13 Jan 2017

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Bacterial Luciferases
Aldehydes
Bioluminescence
Light emission
Substrates
Light
Aliivibrio
Chain length
Luciferases
Carbon
Atoms
Kinetics
Acids
tetradecanal

Fields of Expertise

  • Human- & Biotechnology

Cite this

Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases. / Brodl, Eveline; Ivkovic, Jakov; Tabib, Chaitanya; Breinbauer, Rolf; Macheroux, Peter.

In: Bioorganic & medicinal chemistry, Vol. 25, No. 4, 13.01.2017, p. 1487-1495.

Research output: Contribution to journalArticle

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AU - Tabib,Chaitanya

AU - Breinbauer,Rolf

AU - Macheroux,Peter

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AB - Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490 nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having adouble bond at the a,b-position. These a,b-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decayrate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.

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