C35 bacterial triterpenoids of hopane series : biosynthesis of the C5 side chain Wenjun Liu

To cite this version:

Wenjun Liu. C35 bacterial triterpenoids of hopane series : biosynthesis of the C5 side chain. Other. Université de Strasbourg, 2013. English. ￿NNT : 2013STRAF001￿. ￿tel-01124084￿

HAL Id: tel-01124084 https://tel.archives-ouvertes.fr/tel-01124084 Submitted on 6 Mar 2015

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ÉCOLE DOCTORALE DES SCIENCES CHIMIQUES Institut de chimie de Strasbourg – UMR 7177

THÈSE présentée par Wenjun Liu

soutenue le : 22 Janvier 2013

pour obtenir le grade de

Docteur de l’ Université de Strasbourg Discipline / Spécialité : Chimie

Triterpénoïdes bactériens en C 35 de série hopane: biosynthèse de la chaîne latérale

THÈSE dirigée par : M. Michel ROHMER Professeur, Université de Strasbourg.

RAPPORTEURS : M. Erwan POUPON Professeur, Université de Paris-Sud, C hât enay-Malabry. M. Stéphane VINCENT Professeur, Facultés U niversitaires Notre -Dame de la Paix, Namur.

MEMBRES DU JURY : M. Michel ROHMER Professeur, Université de Strasbourg. M. Philippe SCHAEFFER Directeur de recherche au CNRS, Université de Strasbourg .

MEMBRE INVITÉE: Mme. Anne BODLENNER Maître de Conférences, Université de Strasbourg .

ACKNOWLEDGEMENTS

I am grateful to the following people:

To my director Prof. Michel Rohmer who made me a better scientist, thank you for all of the guidance and support during these years. I appreciate your generous sharing your deep knowledge in not only science but also humanities.

To the members of the committee, Prof. Poupon, Rohmer and Vincent and Dr. Schaeffer, thanks for the valuable comments.

To my master advisor Prof. Pei-Qiang Huang without whose help I would not have the opportunity to pursue my Ph. D study in France.

To my coworkers Drs. E. Takano, E. Kannenberg, T. Härtner, P. Schaeffer, H. Talbot and E. Sakr for the collaboration.

To Dr. Anne Bodlenner, thank you for the numerous discussions and valuable advices for my research work. I appreciate your encouragement and friendship which make me faithful.

To E. Motsch, thanks for GC/MS and MS analysis

To M. Lebreton and H. Nierengarten, thanks for (HR)MS measurements.

To the NMR service (L. Allouche, B. Vincent, J-D. Sauer and M. Coope), thanks for the NMR measurements.

To the rest lovely members in our lab: thanks Catherine G-B for the help on NMR; thanks Denis T. for all the biological questions; thanks Agata L., Anh-Thu N., Clément G., Fanny K., Jeanne T., Mathilde M. and Nader M. for making my life easier; thanks Huguette D., Magalie P., Myriam S., and Philippe C. for your support.

To my parents, my boyfriennd and all my dear friends, many thanks for your generous love and support!

Thanks are due to the international center for frontier research in chemistry, the french embassy and the china scholarship council for financial support.

Content

Abbreviations …………………………………………………………………………………………………………...1

Résumé ……………………………………………………………………………………………………………………..3

General introduction

1. Hopanoids are spread in sediments, eukaryotes and prokaryotes ...... 19 2. Bacteriohopanoids presen