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University of Groningen Exploring (per)oxidases as biocatalysts for the synthesis of valuable aromatic compounds Habib, Mohamed H M

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University of Groningen

Exploring (per)oxidases as biocatalysts for the synthesis of valuable aromatic compounds

Habib, Mohamed H M

DOI:

10.33612/diss.109693881

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below.

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Publication date: 2020

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Habib, M. H. M. (2020). Exploring (per)oxidases as biocatalysts for the synthesis of valuable aromatic compounds. University of Groningen. https://doi.org/10.33612/diss.109693881

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Exploring (per)oxidases as

biocatalysts for the

synthesis of valuable

aromatic compounds

(3)

The research described in this thesis was carried out in the department of Molecular Enzymology of the Groningen Biomolecular Sciences and Biotechnology Institute according to the requirements of the Graduate School of Science, Faculty of Mathematics and Natural Sciences, University of Groningen, The Netherlands. Mohamed Habib received funding from the Cultural Affairs and Missions Sector, Ministry of Higher Education in Egypt.

Cover design: Mohamed Habib and Nina Lindhout Printed by:

ISBN: ISBN:

Copyright © Mohamed Habib 2020, Groningen, The Netherlands.

All rights reserved. No part of this thesis may be reproduced, stored in a retrieval system, or transmitted in any form or by any means without prior permission of the author.

Exploring (per)oxidases as

biocatalysts for the

synthesis of valuable

aromatic compounds

PhD thesis

to obtain the degree of PhD at the

University of Groningen

on the authority of the

Rector Magnificus Prof. C. Wijmenga

and in accordance with

the decision by the College of Deans.

This thesis will be defended in public on

Monday, January 20, 2020 at 12:45 pm hours

by

Mohamed Habib

born on 8 April 1987 in Riyadh, Saudi Arabia

Printed by: Ipskamp Drukkers B.V. ISBN (printed version): 978-94-034-2334-0 ISBN (electronic version): 978-94-034-2335-7

(4)

The research described in this thesis was carried out in the department of Molecular Enzymology of the Groningen Biomolecular Sciences and Biotechnology Institute according to the requirements of the Graduate School of Science, Faculty of Mathematics and Natural Sciences, University of Groningen, The Netherlands. Mohamed Habib received funding from the Cultural Affairs and Missions Sector, Ministry of Higher Education in Egypt.

Cover design: Mohamed Habib and Nina Lindhout Printed by:

ISBN: ISBN:

Copyright © Mohamed Habib 2020, Groningen, The Netherlands.

All rights reserved. No part of this thesis may be reproduced, stored in a retrieval system, or transmitted in any form or by any means without prior permission of the author.

Exploring (per)oxidases as

biocatalysts for the

synthesis of valuable

aromatic compounds

PhD thesis

to obtain the degree of PhD at the

University of Groningen

on the authority of the

Rector Magnificus Prof. C. Wijmenga

and in accordance with

the decision by the College of Deans.

This thesis will be defended in public on

Monday, January 20, 2020 at 12:45 pm hours

by

Mohamed Habib

born on 8 April 1987 in Riyadh, Saudi Arabia

(5)

Supervisors

Prof. M.W. Fraaije Prof. D.B. Janssen

Assessment Committee

Prof. W.J.H. van Berkel Prof. G. Maglia

Prof. F. Hollmann

Table of Contents

Chapter I General introduction: Oxidases and peroxidases and their roles in biocatalysis 7

Chapter II Bacterial enzymes involved in lignin degradation 26

Chapter III A biocatalytic one‐pot approach for the preparation of lignin oligomers using an oxidase/peroxidase cascade enzyme system 51

Chapter IV The biocatalytic synthesis of syringaresinol from 2,6-dimethoxy-4-allylphenol in one-pot using a tailored oxidase/peroxidase system 70

Chapter V Characterization of a new DyP-peroxidase from the alkaliphilic cellulomonad, Cellulomonas bogoriensis 82

Chapter VI Expression and characterization of a resurrected DyP-type peroxidase 100

Summary, Conclusion and Future Outlook 120

Nederlandse Samenvatting 126

Curriculum vitae 131

Acknowledgements 132

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Supervisors

Prof. M.W. Fraaije Prof. D.B. Janssen

Assessment Committee

Prof. W.J.H. van Berkel Prof. G. Maglia

Prof. F. Hollmann

Table of Contents

Chapter I General introduction: Oxidases and peroxidases and their roles in biocatalysis 7

Chapter II Bacterial enzymes involved in lignin degradation 26

Chapter III A biocatalytic one‐pot approach for the preparation of lignin oligomers using an oxidase/peroxidase cascade enzyme system 51

Chapter IV The biocatalytic synthesis of syringaresinol from 2,6-dimethoxy-4-allylphenol in one-pot using a tailored oxidase/peroxidase system 70

Chapter V Characterization of a new DyP-peroxidase from the alkaliphilic cellulomonad, Cellulomonas bogoriensis 82

Chapter VI Expression and characterization of a resurrected DyP-type peroxidase 100

Summary, Conclusion and Future Outlook 120

Nederlandse Samenvatting 126 Curriculum vitae 131 Acknowledgements 132 24 6 48 66 78 96 116 122 128 129

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