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University of Groningen

Bio-orthogonal metal catalysis

de Bruijn, Anne Dowine

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):

de Bruijn, A. D. (2018). Bio-orthogonal metal catalysis: For selective modification of dehydroalanine in

proteins and peptides. Rijksuniversiteit 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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Bio-orthogonal Metal Catalysis

For selective modification of dehydroalanine in proteins and peptides

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The work described in this thesis was carried out at the Stratingh Institute for Chemistry, Rijksuniversiteit Groningen, the Netherlands.

This work has been financially supported by the Ministry of Education, Culture and Science in The Netherlands (Gravitation program no. 024.001.035).

Cover design and lay-out by Dowine de Bruijn.

Cover: metallic palladium on the inner wall of an eppendorf vial, formed from a solution of 50 mM Pd(TFA)2 in methanol/H2O 9:1 (v/v), left standing overnight.

Printed by: Ipskamp Drukkers, Enschede, the Netherlands ISBN

978-94-034-1010-4

printed version

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Bio-orthogonal Metal Catalysis

For selective modification of dehydroalanine

in proteins and peptides

Proefschrift

ter verkrijging van de graad van doctor aan de

Rijksuniversiteit Groningen

op gezag van de

rector magnificus prof. dr. E. Sterken

en volgens besluit van het College voor Promoties.

De openbare verdediging zal plaatsvinden op

vrijdag 2 november 2018 om 12.45 uur

door

Anne Dowine de Bruijn

geboren op 27 mei 1985

te Noordoostpolder

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Promotor

Prof. dr. J.G. Roelfes

Copromotor

Prof. dr. S. Harutyunyan

Beoordelingscommissie

Prof. dr. A.J. Minnaard

Prof. dr. M.D. Witte

Prof. dr. N.I. Martin

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CHAPTER 3

Rhodium mediated transfer hydrogenation

CHAPTER 4

Iridium mediated radical addition

CHAPTER 5

Iridium based photoredox catalysis in water

CHAPTER 6

Conclusion & Perspective

Samenvatting

Acknowledgements

CHAPTER 2

Palladium mediated cross coupling

CHAPTER 1

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Rhodium mediated transfer hydrogenation

Iridium mediated radical addition

Iridium based photoredox catalysis in water

Conclusion & Perspective

Palladium mediated cross coupling

Introduction

9

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106

113

121

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