Pablo Dom-nguez de Mar-a Ionic Liquids in Biotransformations and Organocatalysis Solvents and Beyond.pdf

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IONIC LIQUIDS IN
BIOTRANSFORMATIONS
AND ORGANOCATALYSIS
IONIC LIQUIDS IN
BIOTRANSFORMATIONS
AND ORGANOCATALYSIS
Solvents and Beyond
Edited by
Pablo Domínguez de María
A JOHN WILEY & SONS, INC., PUBLICATION
Copyright © 2012 by John Wiley & Sons, Inc. All rights reserved.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.
Published simultaneously in Canada.
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Library of Congress Cataloging-in-Publication Data:
Ionic liquids in biotransformations and organocatalysis : solvents and beyond / edited by
Pablo Dominguez de Maria.
p. cm.
Includes index.
ISBN 978-0-470-56904-7 (hardback)
1. Proteins–Biotechnology. 2. Ionic solutions. 3. Catalysis. I. Dominguez de Maria, Pablo, 1974-
TP248.65.P76I59 2012
572.6–dc23
2011038032
Printed in the United States of America.
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CONTENTS
Foreword
by Prof. Dr. Roger Sheldon
Preface
Contributors
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xvii
PART I
FUNDAMENTALS
1
IONIC LIQUIDS: DEFINITION, APPLICATIONS, AND CONTEXT FOR
BIOTRANSFORMATIONS AND ORGANOCATALYSIS
Pablo Domínguez de María
1.1 Ionic Liquids: Definition, Development, and Overview of Current
Main Applications
1.2 On the Greenness of ILs: Toward the Third Generation of ILs
and DES
1.3 Context of ILs in Biotransformations and Organocatalysis
References
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IONIC LIQUIDS AND PROTEINS: ACADEMIC AND SOME
PRACTICAL INTERACTIONS
Zhen Yang
Abbreviations for Ionic Liquid Cations
Abbreviations for Ionic Liquid Anions
Abbreviations for Ammonium Ionic Liquids
Other Abbreviations
2.1 Introduction
2.2 Ionic Liquids, Water, and Proteins
2.2.1 Ionic Nature of Ionic Liquids
2.2.2 Protic and Aprotic Ionic Liquids
2.2.3 Water Present in the Ionic Liquids
2.2.4 Interactions of Water and Ionic Liquids with Proteins
2.2.4.1 Effect of Water and Water Activity
2.2.4.2 Effect of Ionic Liquids
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CONTENTS
Hofmeister Effects on Biocatalysis
2.3.1 Hofmeister Effects of Inorganic Salts
2.3.1.1 Quantification of Hofmeister Series
2.3.1.2 Effect of Ions on Protein Stability
2.3.1.3 Effect of Ions on Enzyme Activity
2.3.2 Hofmeister Effects of Ionic Liquids
2.3.2.1 Effect of Ionic Liquid Ions on Enzyme
Performance in Aqueous Solution
2.3.2.2 Kinetic Studies of Enzymes in Ionic
Liquid-Containing Aqueous Solution
2.3.2.3 Enzyme Performance in Ionic
Liquid-Dominating Reaction Systems
2.4 Impact of Ionic Liquids on Enzymes and Proteins
2.4.1 Effect of Ionic Liquids on Enzyme Activity
and Stability
2.4.1.1 Hydrophobicity and Log
P
2.4.1.2 Nucleophilicity and H-bond Basicity
2.4.1.3 Viscosity
2.4.2 Effect of Ionic Liquids on Protein Structure
and Dynamics
2.4.3 Effect of Ionic Liquids on Protein Refolding
and Renaturation
2.4.4 Effect of Ionic Liquids on Protein Crystallization
and Fibrilization
2.5 Protein Extraction by Means of Ionic Liquids
2.5.1 Aqueous/Ionic Liquid–Liquid
Extraction Systems
2.5.2 Ionic Liquid-Based Aqueous
Biphasic Systems
2.5.3 Water-in-Ionic Liquid Microemulsion
Systems
2.6 Proper Selection of Ionic Liquids for Biocatalysis
2.6.1 Amino Acid Ionic Liquids
2.6.2 Ammonium and Phosphonium Ionic
Liquids
2.6.3 Design of Ionic Liquids for Biocatalysis
2.6.4 Proposed Guidelines for Selecting/Designing
Biocompatible Ionic Liquids
2.7 Concluding Remarks
References
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