Synthesis 2017; 49(01): 42-52
DOI: 10.1055/s-0035-1562617
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© Georg Thieme Verlag Stuttgart · New York

Photocaged Carbohydrates: Versatile Tools for Controlling Gene Expression by Light

Claus Bier
a  Institute of Bioorganic Chemistry, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, 52426 Jülich, Germany
,
Dennis Binder
b  Institute of Molecular Enzyme Technology,Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, 52426 Jülich, Germany
,
Dagmar Drobietz
a  Institute of Bioorganic Chemistry, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, 52426 Jülich, Germany
,
Anita Loeschcke
b  Institute of Molecular Enzyme Technology,Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, 52426 Jülich, Germany
,
Thomas Drepper
b  Institute of Molecular Enzyme Technology,Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, 52426 Jülich, Germany
,
Karl-Erich Jaeger
b  Institute of Molecular Enzyme Technology,Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, 52426 Jülich, Germany
c  Institute of Bio- and Geosciences (IBG-1): Biotechnology, Forschungszentrum Jülich, Wilhelm-Johnen-Straße, 52428 Jülich, Germany   eMail: j.pietruszka@fz-juelich.de
,
Jörg Pietruszka*
a  Institute of Bioorganic Chemistry, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, 52426 Jülich, Germany
c  Institute of Bio- and Geosciences (IBG-1): Biotechnology, Forschungszentrum Jülich, Wilhelm-Johnen-Straße, 52428 Jülich, Germany   eMail: j.pietruszka@fz-juelich.de
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Publikationsverlauf

Received: 21. Juli 2016

Accepted: 22. Juli 2016

Publikationsdatum:
13. September 2016 (online)


Dedicated to Prof. Dr. Dieter Enders on the occasion of his 70th birthday

Abstract

The control of biological processes plays a central role in life science, especially the tight regulation of gene expression for biotechnological systems. In this context, optogenetic tools have emerged as an important instrument for controlling gene expression by light with high spatiotemporal resolution in a non-invasive way. Here, we present the syntheses and characterization of biofunctional photocaged carbohydrates, on the basis of the biologically most relevant carbohydrates glucose, galactose, rhamnose, and lactose. The single-step cleavage of these compounds allows both, to rapidly activate and temporary or permanently repress the transcription in E. coli after short UV-A light exposure. This study thus presents a versatile toolbox of photocaged carbohydrates for the light-triggered regulation and control of cellular processes useful for synthetic bio(techno)logy applications.

Supporting Information

 
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