Organoselenium Chemistry: Between Synthesis and Biochemistry


by

Claudio Santi

eISBN: 978-1-60805-838-9, 2014
ISBN: 978-1-60805-839-6



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The use of organoselenium reagents as catalysts is a common thread that runs through the chapters of this book, introducing important ...[view complete introduction]

Table of Contents

Foreword

- Pp. i

Thomas Wirth

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Preface

- Pp. ii-iii (2)

Claudio Santi

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List of Contributors

- Pp. iv-vi (3)

Claudio Santi

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Introduction

- Pp. 3-7 (5)

Claudio Santi

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Electrophilic Selenium Reagents: Addition Reactions to Double Bonds and Selenocyclizations

- Pp. 8-60 (53)

Jacek Ścianowski and Zbigniew Rafiński

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Nucleophilic Selenium: Nucleophilic Substitution

- Pp. 61-93 (33)

Barahman Movassagh and Mozhgan Navidi

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Organoselenium Compounds as Precursor of Radicals

- Pp. 94-119 (26)

Jarosław Lewkowski

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Hypervalent Selenium Derivatives

- Pp. 120-145 (26)

Józef Drabowicz, Piotr Kiełbasiński, Adrian Zając and Patrycja Pokora-Sobczak

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Selenoamides, Synthetic Methods and Recent Progress on their Synthetic Applications

- Pp. 146-165 (20)

Toshiaki Murai

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Enantioselective Catalysis for the Preparation of Organoselenium Compounds and Applications

- Pp. 166-196 (31)

Francesca Marini, Luana Bagnoli and Silvia Sternativo

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Eco-Friendly Access and Application of Organoselenium Reagents: Advances Toward Green Chemistry

- Pp. 197-267 (71)

Antonio L. Braga, Ricardo S. Schwab and Oscar E.D. Rodrigues

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Biochemistry and Nutrition of Selenium: From Inorganic Forms to Endogenous Proteins

- Pp. 268-327 (60)

Bartolini Desirée, Ciffolilli Silvia, Piroddi Marta, Murdolo Giuseppe and Tortoioli Cristina

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Antimicrobial Activity of Organoselenium Compounds

- Pp. 328-344 (17)

Donatella Pietrella

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Selenium and “Bio-Logic” Catalysis: New Bioinspired Catalytic Reactions

- Pp. 345-360 (16)

Caterina Tidei and Claudio Santi

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Antioxidant Organoselenium Molecules

- Pp. 361-378 (18)

Michio Iwaoka

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<sup>77</sup>Se NMR: Theoretical Aspects and Practical Applications

- Pp. 379-415 (37)

Waro Nakanishi and Satoko Hayashi

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Index

- Pp. 418-431 (14)

Claudio Santi

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Foreword

Selenium as a versatile and highly interesting element has primarily concerned chemists but, since the discovery of selenium being an essential trace element, also biologists and biochemists. This book highlights all aspects of current organoselenium chemistry and the editor, Prof. Claudio Santi, has attracted many outstanding contributions to emphasise selenium research at the borderline to biology and medicine. In addition, catalytic reactions are emphasized in many chapters demonstrating the need for sustainable chemistry while still exploiting the unique and advantageous properties of selenium.

This book will be a very valuable source of information for every chemist – in education, in research, and in industry.

Thomas Wirth
Cardiff University
Cardiff, Wales
UK


Preface

In 1817, Jakob Berzelius discovered selenium in the sludge of the lead chambers of the sulphuric acid chamber process of a plant at Gripsholm. Because of its characteristic smelling of tellurium, (tellus = hearth), he named the new element from the Greek word “σελήυη” (Selḕnḕ) meaning goddess of the Moon.

For a long time selenium was considered mainly as a toxic element, and it is currently debated if Marco Polo was the first to write about selenium poisoning. He went to China in 1271 via the ancient Silk Road and in his travelogue in 1295, he wrote that a toxic wild plant collected in the today's Gansu Province killed many cattle.

In 1957 it was found to be an essential trace element as component of the 21th amino acid, selenocysteine and in 1973 the first selenoenzyme, glutathione peroxidase, was isolated. And characterized the development of the organoselenium chemistry has been strongly increased during the last fifty years and nowadays these compounds are efficiently used as intermediates and/or catalysts in a number of organic synthesis: At the same time organoselenium derivatives are currently object of wide investigations for their biological activity, especially, as antiviral, antimicrobial, anticancer, anti-inflammatory and GPx-like mimetics.

This book cover the most recent developments in the field of the classical synthetic application of organoselenium reagents such as electrophilic, nucleophilic and radical reagents focusing the discussion also on the synthesis and the synthetic applications of some emerging classes of compounds such as the hypervalent selenium species and the selenoamides. The use of organoselenium reagents as catalysts is a common thread that runs through the chapters of the book introducing new important aspects of the modern organoselenium chemistry: organocatalysis, green chemistry, bioinspiration, antioxidant activity.

The book also addresses more biological issues such as the antimicrobial activity of organoselenium derivatives and the biochemistry of selenium from the aliments to the selenoproteins.

I’d like to thanks and underline the precious contribute of the 27 distinguished scientists that decided to share their expertise on producing this volume that is the first multidisciplinary approach to the constantly in progress world of organoselenium compounds.

I hope that this book will be read with interest not only by experts but also by students and any other researcher and chemist.

Claudio Santi
Department of Pharmaceutical Sciences
Lab of Catalysis and Green Chemistry
University of Perugia Via del Liceo 1 06100 Perugia
Italy

List of Contributors

Editor(s):
Claudio Santi
Department of Pharmaceutical Sciences
University of Perugia
Perugia
Italy




Contributor(s):
Adrian Zając
Centre of Molecular and Macromolecular Studies
Polish Academy of Sciences
Łódź
Poland


Antonio L. Braga
Federal University of Santa Catarina
Florianópolis
SC
Brazil


Barahman Movassag
Department of Chemistry
K.N. Toosi University of Technology
Tehran
Iran


Caterina Tidei
Department of Pharmaceutical Sciences
University of Perugia
Perugia
Italy


Claudio Santi
Department of Pharmaceutical Sciences
University of Perugia
Perugia
Italy


Tortoioli Cristina
Department of Internal Medicine
Nutrition and Clinical Biochemistry Lab, University of Perugia
Perugia
Italy


Bartolini Desirèe
Department of Internal Medicine
Nutrition and Clinical Biochemistry Lab, University of Perugia
Perugia
Italy


Donatella Pietrella
Department of Pharmaceutical Sciences
University of Perugia
Perugia
Italy


Francesca Marini
Department of Pharmaceutical Sciences
University of Perugia
Perugia
Italy


Francesco Galli
Department of Internal Medicine
Nutrition and Clinical Biochemistry Lab, University of Perugia
Perugia
Italy


Murdolo Giuseppe
Department of Internal Medicine
Nutrition and Clinical Biochemistry Lab, University of Perugia
Perugia
Italy


Jacek Ścianowski
Department of Organic Chemistry, Faculty of Chemistry
Nicolaus Copernicus University -Torun
Poland


Jarosław Lewkowski
University of Łódź, Faculty of Chemistry
Department of Organic Chemistry
Łódź
Poland


Józef Drabowicz
Centre of Molecular and Macromolecular Studies
Polish Academy of Sciences
Łódź
Poland
/
Department of Chemistry, Environment Protection and Biotechnology
Jan Dlugosz University in Czestochowa
Czestochowa
42-200
Poland


Luana Bagnoli
Department of Pharmaceutical Sciences
University of Perugia
Perugia
Italy


Piroddi Marta
Department of Internal Medicine
Nutrition and Clinical Biochemistry Lab, University of Perugia
Perugia
Italy


Michio Iwaoka
Department of Chemistry
School of Science, Tokai University-Tokay
Japan


Mozhgan Navidi
Department of Chemistry
K.N. Toosi University of Technology
Tehran
Iran


Oscar E.D. Rodrigues
Federal University of Santa Maria
Santa Maria
RS
Brazil


Patrycja Pokora-Sobczak
Centre of Molecular and Macromolecular Studies
Polish Academy of Sciences
Łódź
Poland


Piotr Kiełbasiński
Centre of Molecular and Macromolecular Studies
Polish Academy of Sciences
Łódź
Poland


Ricardo S. Schwab
Federal University of São Carlos
São Carlos
SP
Brazil


Satoko Hayashi
Department of Material Science and Chemistry
Faculty of Systems Engineering, Wakayama University
Japan


Ciffolilli Silvia
Department of Internal Medicine
Nutrition and Clinical Biochemistry Lab, University of Perugia
Perugia
Italy


Silvia Sternativo
Department of Pharmaceutical Sciences
University of Perugia
Perugia
Italy


Toshiaki Murai
Department of Chemistry
Faculty of Engineering, Gifu University
Yanagido, Gifu
Japan


Waro Nakanishi
Department of Material Science and Chemistry
Faculty of Systems Engineering, Wakayama University
Japan


Zbigniew Rafiński
Department of Organic Chemistry
Faculty of Chemistry, Nicolaus Copernicus University -Torun
Poland




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