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TERPENECAT SIGNED

Bridging the gap between supramolecular chemistry and current synthetic challenges: Developing artificial catalysts for the tail-to-head terpene cyclization

Total Cost €

EC-Contrib. €

Partnership

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Outcomes and
results

TERPENECAT project word cloud

Explore the words cloud of the TERPENECAT project. It provides you a very rough idea of what is the project "TERPENECAT" about.

nature medication devised precursors head independent self selective greatest organic horizons taxol modified dynamic formed biologically man drugs terpenes selectivity tail artemisinin derivatives active uncharted cancer substrate covalent molecules packages drug selectively conformation malaria mimic natural terpene enzymes predictably source additionally group paclitaxel chemistry synthesis desired belong catalysis enter anticipate cyclization accessible structures diverse unnatural supramolecular variety cyclizations closing routes made catalyst construct catalysts expand poses thereby assembled site chemists gap synthesized tackle learning employed unprecedented utilizing territory family class

Project "TERPENECAT" data sheet

The following table provides information about the project.

Coordinator	UNIVERSITAT BASEL Organization address address: PETERSPLATZ 1 city: BASEL postcode: 4051 website: www.unibas.ch contact info title: n.a. name: n.a. surname: n.a. function: n.a. email: n.a. telephone: n.a. fax: n.a.
Coordinator Country	Switzerland [CH]
Total cost	1˙500˙000 €
EC max contribution	1˙500˙000 € (100%)
Programme	1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
Code Call	ERC-2016-STG
Funding Scheme	ERC-STG
Starting year	2016
Duration (year-month-day)	from 2016-11-01 to 2021-10-31

Partnership

Take a look of project's partnership.

#	participants	country	role	EC contrib. [€]
1	UNIVERSITAT BASEL UNIVERSITAT BASEL Organization address address: PETERSPLATZ 1 city: BASEL postcode: 4051 website: www.unibas.ch contact info title: n.a. name: n.a. surname: n.a. function: n.a. email: n.a. telephone: n.a. fax: n.a.	CH (BASEL)	coordinator	1˙500˙000.00

Map

Project objective

Nature is a rich source of biologically active molecules, among which the largest and most diverse group of natural products are terpenes. Essential drugs like the cancer medication taxol/paclitaxel or the malaria drug artemisinin belong to the terpene family. They are efficiently formed in nature through a so-called tail-to-head terpene cyclization. Chemists are not able to mimic this process with man-made catalysts. This proposal aims at closing this significant research gap by utilizing supramolecular chemistry. Learning how to design such complex catalysts will not only enable us to mimic natural enzymes, but to enter uncharted territory of terpene chemistry.

The main objective is the development of selective catalysts for terpene cyclizations. This certainly poses the greatest challenge within this proposal. Therefore, two independent work packages were devised to tackle this challenge. A novel class of self-assembled catalysts will be developed which are able to control the conformation of the substrate, thereby allowing for selectivity in the cyclization process. The active site of these catalysts can be modified to selectively produce the desired terpene product. Additionally, dynamic covalent chemistry will be employed to construct covalent catalyst structures.

As the second objective, this proposal aims to greatly expand the natural variety of terpenes by utilizing unnatural terpene cyclization precursors. Utilizing the catalysts developed from objective 1, unprecedented artemisinin drug derivatives, which are not accessible via other routes, will be synthesized.

This project will provide catalysts which are able to predictably constrain the conformation of the substrate. Such control is not possible with state-of-the-art catalyst systems. Therefore, I anticipate that this project will open up new horizons in the fields of catalysis and organic synthesis.

Publications

List of publications.
year	authors and title	journal	last update
2019	Qi Zhang, Lorenzo Catti, Leonidas-Dimitrios Syntrivanis, Konrad Tiefenbacher En route to terpene natural products utilizing supramolecular cyclase mimetics published pages: , ISSN: 0265-0568, DOI: 10.1039/c9np00003h	Natural Product Reports	2019-08-06
2018	Qi Zhang, Lorenzo Catti, Konrad Tiefenbacher Catalysis inside the Hexameric Resorcinarene Capsule published pages: 2107-2114, ISSN: 0001-4842, DOI: 10.1021/acs.accounts.8b00320	Accounts of Chemical Research 51/9	2019-08-06
2018	Qi Zhang, Jan Rinkel, Bernd Goldfuss, Jeroen S. Dickschat, Konrad Tiefenbacher Sesquiterpene cyclizations catalysed inside the resorcinarene capsule and application in the short synthesis of isolongifolene and isolongifolenone published pages: 609-615, ISSN: 2520-1158, DOI: 10.1038/s41929-018-0115-4	Nature Catalysis 1/8	2019-08-06
2019	Efrat Pahima, Qi Zhang, Konrad Tiefenbacher, Dan T. Major Discovering Monoterpene Catalysis Inside Nanocapsules with Multiscale Modeling and Experiments published pages: 6234-6246, ISSN: 0002-7863, DOI: 10.1021/jacs.8b13411	Journal of the American Chemical Society 141/15	2019-08-06
2018	Jesper M. KÃ¶ster, Konrad Tiefenbacher Elucidating the Importance of Hydrochloric Acid as a Cocatalyst for Resorcinarene-Capsule-Catalyzed Reactions published pages: , ISSN: 1867-3880, DOI: 10.1002/cctc.201800326	ChemCatChem	2019-06-13
2018	Lorenzo Catti, Konrad Tiefenbacher BrÃ¸nsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201712141	Angewandte Chemie International Edition	2019-06-13
2017	Qi Zhang, Lorenzo Catti, JÃ¼rgen Pleiss, Konrad Tiefenbacher Terpene Cyclizations inside a Supramolecular Catalyst: Leaving-Group-Controlled Product Selectivity and Mechanistic Studies published pages: 11482-11492, ISSN: 0002-7863, DOI: 10.1021/jacs.7b04480	Journal of the American Chemical Society 139/33	2019-06-13
2017	Corina H. Pollok, Qi Zhang, Konrad Tiefenbacher, Christian Merten Chirality Induction from a Chiral Guest to the Hydrogen-Bonding Network of Its Hexameric Resorcinarene Host Capsule published pages: 1987-1991, ISSN: 1439-4235, DOI: 10.1002/cphc.201700610	ChemPhysChem 18/15	2019-06-13

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