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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

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EC-Contrib. €

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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 CH (BASEL) coordinator 1˙500˙000.00

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 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

year authors and title journal last update
List of publications.
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. Köster, 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
Brønsted 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, Jürgen 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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