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University of Groningen Nature-inspired molecules containing multiple electrophilic positions Dockerty, Paul Jacques

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University of Groningen

Nature-inspired molecules containing multiple electrophilic positions

Dockerty, Paul Jacques

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from

it. Please check the document version below.

Document Version

Publisher's PDF, also known as Version of record

Publication date:

2018

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Dockerty, P. J. (2018). Nature-inspired molecules containing multiple electrophilic positions: Synthesis and

application as activity-based probes and inhibitors. University of Groningen.

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Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum.

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Nature-inspired molecules containing

multiple electrophilic positions

Synthesis and application as activity-based probes and inhibitors

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The work described in this thesis was executed at the Stratingh Institute for

Chemistry, University of Groningen, The Netherlands.

Cover design by Oksana Cortes Tolalpa.

Printed by Ipskamp

ISBN: 978-94-034-0310-6

eISBN: 978-94-034-0311-3

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Nature-inspired molecules containing

multiple electrophilic positions

Synthesis and application as activity-based probes and inhibitors

PhD thesis

to obtain the degree of PhD at the

University of Groningen

on the authority of the

Rector Magnificus Prof. E. Sterken

and in accordance with

the decision by the College of Deans.

This thesis will be defended in public on

Friday 9 March 2018 at 14.30 hours

by

Paul Jacques Dockerty

born on 3 May 1988

in Mont-Saint Aignan, France

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Supervisor

Prof. A. J. Minnaard

Co-supervisor

Dr. M.D. Witte

Assessment Committee

Prof. J.G. Roelfes

Prof. S. Verhelst

Prof. R. van der Hoorn

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Nothing in life is to be feared, it is only to be understood. Now is the time to understand more, so that we may fear less.

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Table of contents

Chapter 1

Natural products inspired scaffolds

for activity-based protein profiling

1

Chapter 2

Bicyclic enol cyclocarbamates inhibit

penicillin-binding proteins

23

Chapter 3

Enolcarbamate Probes Label the Aldehyde

Dehydrogenases RALDH1 and ALDH3A1

57

Chapter 4

An original warhead targeting serine hydrolases 79

Chapter 5

An NMR study to help the design of

more potent probes

101

Chapter 6

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