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1 Cover Page The handle holds various files of this Leiden University dissertation. Author: Jong, Ana Rae de Title: Development of synthetic procedures towards immunostimulating carbohydrates Issue Date:

2 List of Publications Chirality of TLR-2 ligand Pam 3 CysSK 4 in fully synthetic peptide conjugates critically influences the induction of specific CD8+ T-cells Selina Khana, Jimmy J. Weterings, Cedrik M. Britten, Ana R. de Jong, Dirk Graafland, Cornelis J. M. Melief, Sjoerd H. van der Burg, Gijsbert A. van der Marel, Herman S. Overkleeft, Dmitri V. Filippov, Ferry Ossendorp. Molecular Immunology, 2009, 46, The Stereodirecting Effect of the Glycosyl C5-Carboxylate Ester: Stereoselective Synthesis of -Mannuronic Acid Alginates Jeroen D. C. Codée, Leendert J. van den Bos, Ana R. de Jong, Jasper Dinkelaar, Gerrit Lodder, Herman S. Overkleeft, and Gijsbert A. van der Marel. Journal of Organic Chemistry, 2009, 74, Stereodirecting Effect of the Pyranosyl C-5 Substituent in Glycosylation Reactions Jasper Dinkelaar, Ana R. de Jong, Robert van Meer, Mark Somers, Gerrit Lodder, Herman S. Overkleeft, Jeroen D. C. Codée, and Gijsbert A. van der Marel. Journal of Organic Chemistry, 2009, 74, Stereoselectivity of glycosylations of conformationally restricted mannuronate esters Jeroen D. C. Codée, Ana R. de Jong, Jasper Dinkelaar, Herman S. Overkleeft, Gijsbert A. van der Marel. Tetrahedron, 2009, 65,

3 Mannuronic Acids: Reactivity and Selectivity Jeroen D. C. Codée, Marthe T. C. Walvoort, Ana R. de Jong, Gerrit Lodder, Herman S. Overkleeft, and Gijsbert A. van der Marel. Journal of Carbohydrate Chemistry, 2011, 30, Exploring and Exploiting the Reactivity of Glucuronic Acid Donors Ana R. de Jong, Bas Hagen, Vincent van der Ark, Herman S. Overkleeft, Jeroen D. C. Code e, and Gijsbert A. van der Marel. Journal of Organic Chemistry, 2012, 77, A Second-Generation Tandem Ring-Closing Metathesis Cleavable Linker for Solid Phase Oligosaccharide Synthesis Ana R. de Jong, Anne G. Volbeda, Bas Hagen, Hans van den Elst, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée, European Journal of Organic Chemistry, 2013, 29,

4 Curriculum Vitae Ana Rae de Jong werd geboren op 23 september 1986 te Inchun-Kun (Zuid-Korea). Na het behalen van het gymnasium diploma aan t Visser het Hooft lyceum te Leiden in 2004 werd in dat jaar begonnen met de studie Scheikunde aan de Universiteit Leiden. Het propedeutisch examen werd in augustus 2005 afgelegd, gevolgd door de bachelor en masteropleiding Chemistry (Design & Synthesis). In 2006 werd een bachelorstage gedaan in de vakgroep Bioorganische chemie, onder leiding van dr. J.J. Weterings en dr. D.V. Filippov en behelsde de synthese van Pam 3 Cys conjugaten en een 7-hydro-8-oxo-adenine analoog. Tijdens de daaropvolgende master stage werd er onder begeleiding van dr. J.D.C. Codée en prof. dr. G.A. van der Marel onderzoek gedaan aan conformationeel vastgelegde mannuronzuur donoren en de stereoselectiviteit van een serie glycosiden en de corresponderende glycuronzuur esters. Een industriële bijvakstage werd uitgevoerd bij MSD (toen Schering-Plough) op de afdeling Medicinal Chemistry Oss (MCO) in de groep van dr. J.C.H.M Wijkmans, onder begeleiding van dr. C.E.P. Maljaars en ing. I.A.M. Huisman en omvatte de synthese van designer TLR-4 liganden. Van februari 2009 tot juli 2013 werd als assistent in opleiding gewerkt aan het in dit proefschrift beschreven onderzoek binnen de vakgroep Bio-organische synthese onder supervisie van Prof. dr. G.A. van der Marel en dr. J.D.C. Codée. Gedeelten van het onderzoek werden gepresenteerd in de vorm van posters op de jaarlijkse NWO Design and Synthesis bijeenkomsten, op het 16th European Carbohydrate symposium 2011 in Sorrento en op het 6th Glycan forum te Berlijn. Tevens werd er in juli 2009 deelgenomen aan de HRSMC summer school New horizons in synthetic methodology in Maastricht. In april 2013 werd een mondelinge presentatie gegeven tijdens het Organische Chemie Symposium georganiseerd door de KNCV Organische Chemie divisie en NWO-CW studiegroepen te Wageningen. Sinds 16 september 2013 is de auteur van dit proefschrift werkzaam als junior recruiter bij BIRD Recruitment

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List of publications

List of publications List of publications Kimberly M. Bonger, Sascha Hoogendoorn, Chris J. van Koppen, Cornelis M. Timmers, Herman S. Overkleeft, Gijsbert A. van der Marel. Synthesis and biological evaluation of heterodimeric

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