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The handle http://hdl.handle.net/1887/19990 holds various files of this Leiden University dissertation.

Author: Walvoort, Maria Theresia Cornelia

Title: On the reactivity and selectivity of donor glycosides in glycochemistry and glycobiology

Date: 2012-10-18

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List of Publications

Equatorial anomeric triflates from mannuronic acid esters

M. T. C. Walvoort, G. Lodder, J. Mazurek, H. S. Overkleeft, J. D. C. Codée, G. A. van der Marel

Journal of the American Chemical Society 2009, 131 (34), 12080-12081.

The impact of oxacarbenium ion conformers on the stereochemical outcome of glycosylations

M. T. C. Walvoort, J. Dinkelaar, L. J. van den Bos, G. Lodder, H. S. Overkleeft, J. D. C.

Codée, G. A. van der Marel

Carbohydrate Research 2010, 345 (10), 1252-1263.

Mannosazide methyl uronate donors. Glycosylating properties and use in the construction of β-ManNAcA-containing oligosaccharides

M. T. C. Walvoort, G. Lodder, H. S. Overkleeft, J. D. C. Codée, G. A. van der Marel The Journal of Organic Chemistry 2010, 75 (23), 7990-8002.

Uronic acids in oligosaccharide and glycoconjugate synthesis

J. D. C. Codée, A. E. Christina, M. T. C. Walvoort, H. S. Overkleeft, G. A. van der Marel Topics in Current Chemistry 2011, 301, 253-289.

Synthesis of methyl glycuronates by stereo- and regioselective TEMPO/BAIB- oxidation

M. T. C. Walvoort, D. Sail, G. A. van der Marel, J. D. C. Codée Carbohydrate Chemistry Proven Methods 2011, 1, Ch. 11, p. 99.

Activity-based profiling of retaining β β-glucosidases: a comparative study β β

M. T. C. Walvoort, M. D. Witte, K.-Y. Li, W. W. Kallemeijn, W. E. Donker-Koopman, R.

G. Boot, J. M. F. G. Aerts, J. D. C. Codée, G. A. van der Marel, H. S. Overkleeft Chembiochem 2011, 12 (8), 1263-1269.

Stereoselective synthesis of 2,3-diamino-2,3-dideoxy-β-

D

-mannopyranosyl uronates M. T. C. Walvoort, G.-J. Moggré, G. Lodder, H. S. Overkleeft, J. D. C. Codée, G. A. van der Marel

The Journal of Organic Chemistry 2011, 76 (18), 7301-7315.

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Mannopyranosyl uronic acid donor reactivity

M. T. C. Walvoort, W. de Witte, J. van Dijk, J. Dinkelaar, G. Lodder, H. S. Overkleeft, J.

D. C. Codée, G. A. van der Marel

Organic Letters 2011, 13 (16), 4360-4363.

Mannuronic acids: reactivity and selectivity

J. D. C. Codée, M. T. C. Walvoort, A.-R. de Jong, J. Dinkelaar, G. Lodder, H. S.

Overkleeft, G. A. van der Marel

Journal of Carbohydrate Chemistry 2011, 30 (7-9), 438-457.

Synthesis of β β β β-mannuronic acid oligosaccharides

Patent Ancora Pharmaceuticals, 2011, US patent No.: 13333-25.

Automated solid-phase synthesis of β β-mannuronic acid alginates β β

M. T. C. Walvoort, H. van den Elst, O. J. Plante, L. Kröck, P. H. Seeberger, H. S.

Overkleeft, G. A. van der Marel, J. D. C. Codée

Angewandte Chemie International Edition 2012, 51 (18), 4393-4396.

Highlighted by Nature Chemical Biology 2012, 8 (4), 321.

Automated solid-phase synthesis of hyaluronan oligosaccharides

M. T. C. Walvoort, A. G. Volbeda, N. R. M. Reintjens, H. van den Elst, O. J. Plante, H. S.

Overkleeft, G. A. van der Marel, J. D. C. Codée Organic Letters 2012, 14 (14), 3776-3779.

Tuning of 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β β β β- glucosidase probes

M. T. C. Walvoort, W. W. Kallemeijn, L. I. Willems, M. D. Witte, J. M. F. G. Aerts, G. A.

van der Marel, J. D. C. Codée, H. S. Overkleeft

Chemical Communications 2012, in press (DOI: 10.1039/C2CC35653H)

On the reactivity and selectivity of donor glycosides in glycochemistry and glycobiology

M. T. C. Walvoort, G. A. van der Marel, H. S. Overkleeft, J. D. C. Codée

Manuscript in preparation

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Curriculum Vitae - Dutch

De auteur van dit proefschrift werd geboren op 26 mei 1983 te Utrecht. In 2001 legde ze het eindexamen van het Christelijk Gymnasium Utrecht (profielen Natuur-Gezondheid &

Natuur-Techniek) met goed gevolg af. Aansluitend werd begonnen met de propedeuse Scheikunde, gevolg door de doctoraalstudie Chemistry – Design & Synthese, beide aan de Universiteit Leiden.

In 2004 deed ze haar eerste onderzoekservaring op in de vakgroep Bio-Organische Chemie (prof. dr. H. S. Overkleeft en prof. dr. G. A. van der Marel) in het project getiteld

‘Preparation of a dual action antibiotic & synthesis and biological evaluation of antimicrobial gels based on quaternary ammonium salts’, begeleid door dr. P. C. de Visser.

In dezelfde vakgroep werd in 2005-2006 de hoofdvakstage uitgevoerd onder begeleiding van dr. ing. K. M. Bonger getiteld ‘On the synthesis of guanine-derived tryptase inhibitors’.

Een bijvakstage in de groep van prof. dr. B. G. Davis (Oxford University, UK) werd ondernomen in 2006-2007, getiteld ‘Towards the synthesis of disulfide-linked glycopeptides’. In augustus 2007 werd het doctoraaldiploma met succes behaald.

Het promotie-onderzoek hier beschreven werd begonnen in september 2007, onder begeleiding van prof. dr. G. A. van der Marel en prof. dr. H. S. Overkleeft. Delen van dit onderzoek zijn gepresenteerd tijdens de jaarlijkse NWO-CW Synthesis and Design conferenties in Lunteren (NL) middels posters (2008-2010) en een mondelinge presentatie (2010). Een posterpresentatie is gegeven op het 15

e

European Carbohydrate Symposium in 2009 (Wenen, Oostenrijk), en bekroond met een posterprijs. Tevens zijn een poster- en mondelinge presentatie gegeven op het 16

e

European Carbohydrate Symposium in 2011 (Sorrento, Italië). Tijdens het promotietraject heeft de auteur de cursussen ‘Drug Discovery Cycle’ en ‘Business & Entrepreneurial Skills’, georganiseerd door TI Pharma, ‘Purification processes with HPAEC-PAD’ van Dionex Amsterdam, en de zomerschool ‘New horizons in synthetic methodology’ van de HRSMC graduate school bijgewoond.

Per 1 juli 2012 is de auteur van dit proefschrift als post-doctoraal onderzoeker werkzaam in

de vakgroep van prof. B. Imperiali, aan de faculteit Biology van het Massachusetts Institute

of Technology (Cambridge, USA).

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Curriculum Vitae - English

The author was born in Utrecht on May 26

th

1983. In 2001 she completed the high school Christelijk Gymnasium Utrecht (majors in Life Science & Technology). Subsequently she started the study Chemistry at the Leiden University, followed by obtaining a master’s degree in Chemistry – Design & Synthesis in 2007.

In 2004 she obtained her first research experience in the group Bio-Organic Synthesis (prof. dr. H. S. Overkleeft and prof. dr. G. A. van der Marel) at the Leiden University (NL) in the project entitled ‘Preparation of a dual action antibiotic & synthesis and biological evaluation of antimicrobial gels based on quaternary ammonium salts’, under supervision of dr. P. C. de Visser. In the same research group she undertook her master’s internship in 2005-2006, supervised by dr. ing. K. M. Bonger entitled ‘On the synthesis of guanine- derived tryptase inhibitors’. An international internship was performed in 2006-2007 in the group of prof. dr. B. G. Davis (Oxford University, UK) entitled ‘Towards the synthesis of disulfide-linked glycopeptides’.

The doctoral studies presented here commenced in September 2007 under the supervision of prof. dr. G. A. van der Marel and prof. dr. H. S. Overkleeft. Parts of this research were presented as posters (2008-2010) and an oral presentation (2010) at the annual meetings of the NWO-CW division Synthesis and Design in Lunteren (NL). A poster was presented at the 15

th

European Carbohydrate Symposium in 2009 (Vienna, Austria), and awarded with a poster prize. At the 16

th

European Carbohydrate Symposium in 2011 (Sorrento, Italy), an oral and poster presentation were given. During her PhD studies the author participated in the courses ‘Drug Discovery Cycle’ and ‘Business & Entrepreneurial Skills’, as organized by TI Pharma, ‘Purification processes with HPAEC-PAD’ from Dionex Amsterdam, and the summer school ‘New horizons in synthetic methodology’ from the HRSMC graduate school.

As of July 2012, the author of this Thesis is employed as a postdoctoral associate in the

group of prof. B. Imperiali, at the Biology department of Massachusetts Institute of

Technology (Cambridge, USA).

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