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Rapid Access to a Broad Range of 6'-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors.

ABSTRACT: Light-emitting firefly luciferin analogues contain electron-donating groups in the 6'-position, but the scope of known 6'-substitution remains narrow. A two-step route to a broad range of 6'-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6'-functionality. This chemistry allowed direct access to "caged" amide and bright azetidine analogues, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives.

SUBMITTER: Sharma DK

PROVIDER: S-EPMC5836729 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Rapid Access to a Broad Range of 6'-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors.

Sharma Deepak K DK Adams Spencer T ST Liebmann Kate L KL Miller Stephen C SC

Organic letters 20171101 21

Light-emitting firefly luciferin analogues contain electron-donating groups in the 6'-position, but the scope of known 6'-substitution remains narrow. A two-step route to a broad range of 6'-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6'-functionality. This chemistry allowed direct access to "caged" amide and bright azetidine analogues, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives. ...[more]

PMID: 29039673

Similar Datasets

Biosynthesis of firefly luciferin in adult lantern: decarboxylation of L-cysteine is a key step for benzothiazole ring formation in firefly luciferin synthesis.

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Correction: Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of L-Cysteine is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis

Project description: Not available

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A selenium analogue of firefly D-luciferin with red-shifted bioluminescence emission.

Project description:A selenium analogue of amino-D-luciferin, aminoseleno-D-luciferin, is synthesized and shown to be a competent substrate for the firefly luciferase enzyme. It has a red-shifted bioluminescence emission maximum at 600 nm and is suitable for bioluminescence imaging studies in living subjects.

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Firefly luciferase can use L-luciferin to produce light.

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Project description:An efficient synthetic strategy for rapid access to analogues of peloruside A has been demonstrated. The synthetic route was highlighted by a simple esterification-based fragment coupling and a late stage ring-closing metathesis reaction. This convergent route has provided access to rationally designed analogues inspired by the solution conformational preferences of peloruside A.

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Computational investigation into the fluorescence of luciferin analogues.

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| S-EPMC8706149 | biostudies-literature

Evaluating Brightness and Spectral Properties of Click Beetle and Firefly Luciferases Using Luciferin Analogues: Identification of Preferred Pairings of Luciferase and Substrate for In Vivo Bioluminescence Imaging.

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