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C-Xaq

Cross-Coupling (C-X): Pioneering Mild Aqueous Cross-Coupling Methodologies to Enable Selective Functionalisation and Diversification of Halogenated Natural Products

Total Cost €

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EC-Contrib. €

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Partnership

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Project "C-Xaq" data sheet

The following table provides information about the project.

Coordinator
THE UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS 

Organization address
address: NORTH STREET 66 COLLEGE GATE
city: ST ANDREWS
postcode: KY16 9AJ
website: www.st-andrews.ac.uk

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 United Kingdom [UK]
 Project website http://rjmg.wp.st-andrews.ac.uk/research/
 Total cost 183˙454 €
 EC max contribution 183˙454 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2014
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2015
 Duration (year-month-day) from 2015-05-01   to  2017-04-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    THE UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS UK (ST ANDREWS) coordinator 183˙454.00

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 Project objective

Natural Products (NPs) are key to medicine, yet the generation of analogues of these important compounds can often be challenging. I propose to investigate an exciting new approach to NP analogues pioneered by the Goss lab. By developing new, mild, aqueous and selective cross-coupling chemistries I will enable the selective diversification of organic molecules, and in particular NPs, containing carbon-halogen bonds. With my expertise in organometallic chemistry and computational chemistry and in collaboration with the Goss lab, we are poised to bring significant advance to this new field of research. Over 5000 halogenated NPs have been isolated and identified to date, presenting a series of attractive test-beds for this proposed research. Additionally, with the advent of synthetic biology, it has recently been possible for the Goss group and others to engineer new to nature NPs containing halogen handles. The Goss group demonstrated selective functionalization of these NPs developing and using mild and aqueous Suzuki Miyaura cross-coupling conditions. Building upon this success, I will develop methodology to enable, under mild aqueous conditions, a greater diversity of cross-coupling reactions of aryl halide containing small molecules and then NPs to be employed. I will then embrace the challenge of the selective functionalization of the less reactive vinyl and alkyl halides, first in the presence of small molecules and then in the context of NPs. My reaction design, in this challenging area, will be informed by recent literature precedent, and my own DFT calculations. Success will both enable access to libraries of previously inaccessible NP analogues and provide the first steps toward being able to carry out these chemical reactions in tissues and perhaps even in live organisms in a bioorthogonal manner.

 Publications

year authors and title journal last update
List of publications.
2017 M. J. Corr, S. V. Sharma, C. Pubill-Ulldemolins, R. T. Bown, P. Poirot, D. R. M. Smith, C. Cartmell, A. Abou Fayad, R. J. M. Goss
Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
published pages: 2039-2046, ISSN: 2041-6520, DOI: 10.1039/C6SC04423A
Chem. Sci. 8/3 2019-07-24

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