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The handle https://hdl.handle.net/1887/3135040 holds various files of this Leiden

University dissertation.

Author: Boer, C. de

Title: Inhibitors and probes targeting endo-glycosidases Issue Date: 2021-02-11

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INHIBITORS AND PROBES

TARGETING

ENDO-GLYCOSIDASES

PROEFSCHRIFT

ter verkrijging van

de graad van Doctor aan de Universiteit Leiden, op gezag van de Rector Magnificus prof.dr.ir. H. Bijl,

volgens besluit van het College voor Promoties te verdedigen op donderdag 11 februari 2021

klokke 11:15 uur

door

Casper de Boer

geboren te Heemskerk in 1991

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Promotiecommissie

Promotores: Prof. dr. H.S. Overkleeft Prof. dr. J.D.C. Codée Overige Leden: Prof. dr. G.A. van der Marel

Prof. dr. M. van der Stelt

Prof. dr. G.J. Davies (University of York, United Kingdom) Prof. dr. H. Wennemers (ETH Zürich, Switzerland)

Prof. dr. F. Pfrengle (BOKU, Austria)

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Table of contents

1

General introduction 5

2

Activity-based probes targeting glycosidases

acting on plant glycans 19

3

Mechanism-based heparanase inhibitors and activity-based probes 59

4

Synthesis of an activity-based probe based on the Psl motif 101

5

Summary and future prospects 117

Nederlandse samenvatting 139

Publications 142

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