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Cover Page

The handle

http://hdl.handle.net/1887/67530

holds various files of this Leiden University

dissertation.

Author: Gential, G.P.P.

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Self adjuvanting immunopeptides: Design

and synthesis

PROEFSCHRIFT

ter verkrijging van

de graad van Doctor aan de Universiteit Leiden op gezag van Rector Magnificus prof. mr. C. J. J. M. Stolker,

volgens besluit van het College voor Promoties te verdedigen op donderdag 17 december 2018

klokke 13:45 uur

door

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2

Promotion commissie

Promotores : Prof.dr. F.A. Ossendorp Prof.dr. G.A. van der Marel Co-promotor : Dr. D.V. Filippov

Overige leden : Prof.dr. H. S. Overkleeft Prof.dr. Prof.dr. J. Brouwer Prof.dr. H. Ovaa

Prof.dr. A. Geluk Dr. M. Verdoes Dr. S.I. van Kasteren

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3

Table of contents

Chapter 1: Introduction 5 Chapter 2: Synthesis and evaluation of fluorescent Pam3Cys peptide conjugates 21 Chapter 3 : Design, synthesis and immunological evaluation

of simplified self-adjuvanting TLR-2 stimulating peptides 35 Chapter 4 : Synthesis of TLR-7 peptide conjugates 57 Chapter 5 : Phosphine reactivity towards azides in water: Reduction versus hydrolysis 67 Chapter 6 : Towards convergent synthesis of viral VPg proteins linked to RNA 77 Chapter 7 : Summary and future prospects 107

Resumé 113

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