M ETHODS IN MOLECULAR BIOLOGY

Transcription

1 M ETHODS IN MOLECULAR BIOLOGY Series Editor John M. Walker School of Life Sciences University of Hertfordshire Hat fi eld, Hertfordshire, AL10 9AB, UK For further volumes:

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3 Immobilization of Enzymes and Cells Third Edition Edited by Jose M. Guisan Instituto de Catalisis y Petroleoquimica, CSIC, Madrid, Spain

4 Editor Jose M. Guisan Instituto de Catalisis y Petroleoquimica, CSIC Madrid, Spain ISSN ISSN (electronic) ISBN ISBN (ebook) DOI / Springer New York Heidelberg Dordrecht London Library of Congress Control Number: Springer Science+Business Media New York 2013 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. Exempted from this legal reservation are brief excerpts in connection with reviews or scholarly analysis or material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Duplication of this publication or parts thereof is permitted only under the provisions of the Copyright Law of the Publisher s location, in its current version, and permission for use must always be obtained from Springer. Permissions for use may be obtained through RightsLink at the Copyright Clearance Center. Violations are liable to prosecution under the respective Copyright Law. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. While the advice and information in this book are believed to be true and accurate at the date of publication, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein. Printed on acid-free paper Humana Press is a brand of Springer Springer is part of Springer Science+Business Media (

5 Pref ace Enzymes and whole cells are able to catalyze the most complex chemical processes under the most benign experimental and environmental conditions. In this way, enzymes and cells could be excellent catalysts for a much more sustainable chemical industry. However, enzymes and cells have also some limitations for nonbiological applications: fine chemistry, food chemistry, analysis, therapeutics, and so on. Enzymes and cells may be unstable, difficult to handle under nonconventional conditions, poorly selective towards synthetic substrates, etc. From this point of view, the transformation, from the laboratory to the industry, of chemical processes catalyzed by enzymes and cells may be one of the most complex and exciting goals in biotechnology. For most of the industrial applications, enzymes and cells have to be immobilized, via very simple and cost-effective protocols, in order to be reused for very long periods of time. From this point of view, immobilization, simplicity, and stabilization have to be strongly related concepts. For the last 30 years a number of protocols for immobilization of cells and enzymes have been reported in scientific literature. However, only very few protocols are simple enough and only very few protocols are useful enough to greatly improve the functional properties of enzymes and cells: activity, stability, selectivity, etc. The third edition of Immobilization of Enzymes and Cells intends to be an update as well as a complement of the two previous editions. This volume now includes the following aspects of old and new protocols for immobilization: 1. Very simple protocols for immobilization of enzymes and cells which could be very useful for application at industrial scale. 2. Immobilization protocols useful to greatly improve functional properties of enzymes and cells. There is still a long and exciting way to develop very simple and very efficient protocols for the preparation, characterization, and utilization of immobilized enzymes and cells. This volume tries to show some very interesting results already obtained and, at the same time, it intends to persuade to the readers for working in a further development of even more important protocols of immobilization. Very likely, the development of excellent protocols for immobilization will promote a massive implementation of enzyme and cells as industrial biocatalysts. This implementation could be decisive for the development of a much more skilled and sustainable chemical industry: the cost-effective production of very complex and useful molecules under the mildest conditions. Jose M. Guisan v

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7 Contents Preface Contributors v ix 1 New Opportunities for Immobilization of Enzymes Jose M. Guisan 2 Immobilization of Enzymes: A Literature Survey Beatriz Brena, Paula González-Pombo, and Francisco Batista-Viera 3 Glutaraldehyde-Mediated Protein Immobilization Fernando López-Gallego, Jose M. Guisán, and Lorena Betancor 4 Immobilization of Enzymes on Monofunctional and Heterofunctional Epoxy-Activated Supports Cesar Mateo, Valeria Grazu, and Jose M. Guisan 5 Stabilization of Enzymes by Multipoint Covalent Immobilization on Supports Activated with Glyoxyl Groups Fernando López-Gallego, Gloria Fernandez-Lorente, Javier Rocha- Martin, Juan M. Bolivar, Cesar Mateo, and Jose M. Guisan 6 Oriented Covalent Immobilization of Enzymes on Heterofunctional-Glyoxyl Supports Cesar Mateo, Gloria Fernandez-Lorente, Javier Rocha-Martin, Juan M. Bolivar, and Jose M. Guisan 7 Reversible Covalent Immobilization of Enzymes via Disulfide Bonds Karen Ovsejevi, Carmen Manta, and Francisco Batista-Viera 8 Immobilization of Candida rugosa Lipase on Superparamagnetic Fe 3 O 4 Nanoparticles for Biocatalysis in Low-Water Media Joyeeta Mukherjee, Kusum Solanki, and Munishwar Nath Gupta 9 Immobilization of Enzymes by Bioaffinity Layering Veena Singh, Meryam Sardar, and Munishwar Nath Gupta 10 Immobilization of Enzymes on Magnetic Beads Through Affinity Interactions 139 Audrey Sassolas, Akhtar Hayat, and Jean-Louis Marty 11 Tips for the Functionalization of Nanoparticles with Antibodies Ester Polo, Sara Puertas, María Moros, Pilar Batalla, José M. Guisán, Jesús M. de la Fuente, and Valeria Grazú 12 Design and Characterization of Functional Nanoparticles for Enhanced Bio-performance Pablo del Pino, Scott G. Mitchell, and Beatriz Pelaz vii

8 viii Contents 13 Immobilization of Enzymes on Ethynyl-Modified Electrodes via Click Chemistry Akhtar Hayat, Audrey Sassolas, Amina Rhouati, and Jean-Louis Marty 14 Modification of Carbon Nanotube Electrodes with 1-Pyrenebutanoic Acid, Succinimidyl Ester for Enhanced Bioelectrocatalysis Guinevere Strack, Robert Nichols, Plamen Atanassov, Heather R. Luckarift, and Glenn R. Johnson 15 Enzyme Immobilization by Entrapment Within a Gel Network Audrey Sassolas, Akhtar Hayat, and Jean-Louis Marty 16 Practical Protocols for Lipase Immobilization via Sol Gel Techniques Manfred T. Reetz 17 Improving Lipase Activity by Immobilization and Post- immobilization Strategies Jose M. Palomo, Marco Filice, Oscar Romero, and Jose M. Guisan 18 High Activity Preparations of Lipases and Proteases for Catalysis in Low Water Containing Organic Solvents and Ionic Liquids Ipsita Roy, Joyeeta Mukherjee, and Munishwar Nath Gupta 19 Biomedical Applications of Immobilized Enzymes: An Update Marta Pastor, Amaia Esquisabel, and José Luis Pedraz 20 Immobilization of Whole Cells by Chemical Vapor Deposition of Silica Susan R. Sizemore, Robert Nichols, Randi Tatum, Plamen Atanassov, Glenn R. Johnson, and Heather R. Luckarift 21 Encapsulation of Cells in Alginate Gels Pello Sánchez, Rosa María Hernández, José Luis Pedraz, and Gorka Orive 22 Microalgal Immobilization Methods Ignacio Moreno-Garrido 23 Therapeutic Applications of Encapsulated Cells Argia Acarregui, Gorka Orive, José Luis Pedraz, and Rosa María Hernández 24 Whole Cell Entrapment Techniques Jorge A. Trelles and Cintia W. Rivero Index

9 Contributors ARGIA ACARREGUI NanoBioCel Group, Laboratory of Pharmaceutics, School of Pharmacy, University of the Basque Country (UPV/EHU), Vitoria-Gasteiz, Spain PLAMEN ATANASSOV Department of Chemical and Nuclear Engineering, Center for Emerging Energy Technologies, University of New Mexico, Albuquerque, NM, USA PILAR BATALLA Department of Analytical Chemistry, Physical Chemistry and Chemical Engineering, Faculty of Chemistry, University of Alcalá, FRANCISCO BATISTA-VIERA Cátedra de Bioquímica, Departamento de Biociencias, Facultad de Química, Universidad de la República, Montevideo, Uruguay LORENA BETANCOR Laboratorio de Biotecnología, Facultad de Ingeniería, Universidad ORT Uruguay, Montevideo, Uruguay JUAN M. BOLIVAR Institute of Catalysis, CSIC, CAMPUS UAM-Cantoblanco, BEATRIZ BRENA Cátedra de Bioquímica, Departamento de Biociencias, Facultad de Química, Universidad de la República, Montevideo, Uruguay AMAIA ESQUISABEL NanoBioCel Group, Laboratory of Pharmaceutics, School of Pharmacy, University of the Basque Country, Vitoria-Gasteiz, Spain ; Networking Biomedical Research Center on Bioengineering, Biomaterials and Nanomedicine, CIBER-BBN, Vitoria-Gasteiz, Spain GLORIA FERNANDEZ-LORENTE Instituto de Investigación en Ciencias de la Alimentación (CIAL) CSIC-UAM, MARCO FILICE Institute of Catalysis, CSIC, CAMPUS UAM-Cantoblanco, JESÚS M. DE LA FUENTE Nanotherapy and Nanodiagnostics Group (GN2), Instituto de Nanociencia de Aragón (INA), Universidad de Zaragoza, and Fundación ARAID, Zaragoza, Spain PAULA GONZÁLEZ-POMBO Cátedra de Bioquímica, Departamento de Biociencias, Facultad de Química, Universidad de la República, Montevideo, Uruguay VALERIA GRAZU Nanotherapy and Nanodiagnostics Group (GN2), Instituto de Nanociencia de Aragón, Universidad de Zaragoza, Zaragoza, Spain JOSE M. GUISAN Instituto de Catalisis y Petroleoquimica, CSIC, MUNISHWAR NATH GUPTA Department of Chemistry, Indian Institute of Technology Delhi, New Delhi, India AKHTAR HAYAT IMAGES EA 4218, University of Perpignan, Perpignan Cedex, France ROSA MARÍA HERNÁNDEZ NanoBioCel Group, Laboratory of Pharmaceutics, School of Pharmacy, University of the Basque Country (UPV/EHU), Vitoria-Gasteiz, Spain GLENN R. JOHNSON Air Force Research Laboratory, Airbase Sciences, Tyndall AFB, FL, USA; Integration Innovation Inc (i3), Huntsville, AL, USA FERNANDO LÓPEZ-GALLEGO Institute of Catalysis, CSIC, CAMPUS UAM- Cantoblanco, ix

10 x Contributors HEATHER R. LUCKARIFT Universal Technology Corporation, Dayton, OH, USA ; Airbase Sciences Branch, Air Force Research Laboratory, Tyndall Air Force Base, Panama city, FL, USA CARMEN MANTA Cátedra de Bioquímica, Departamento de Biociencias, Facultad de Química, Universidad de la República, Montevideo, Uruguay JEAN-LOUIS MARTY IMAGES EA 4218, University of Perpignan, Perpignan Cedex, France CESAR MATEO Institute of Catalysis, CSIC, CAMPUS UAM-Cantoblanco, SCOTT G. MITCHELL Nanotherapy and Nanodiagnostics Group (GN2), Campus Rio Ebro, Instituto de Nanociencia de Aragón, Universidad de Zaragoza, Zaragoza, Spain IGNACIO MORENO-GARRIDO Department of Ecology and Coastal Management, Institute of Marine Sciences of Andalucia (ICMAN-CSIC), Cádiz, Spain MARÍA MOROS Nanotherapy and Nanodiagnostics Group (GN2), Instituto de Nanociencia de Aragón (INA), Universidad de Zaragoza, Zaragoza, Spain JOYEETA MUKHERJEE Department of Chemistry, Indian Institute of Technology Delhi, New Delhi, India ROBERT NICHOLS Universal Technology Corporation, Dayton, OH, USA ; Airbase Sciences Branch, Air Force Research Laboratory, Tyndall Air Force Base, Panama city, FL, USA GORKA ORIVE NanoBioCel Group, Laboratory of Pharmaceutics, School of Pharmacy, University of the Basque Country (UPV/EHU), Vitoria-Gasteiz, Spain KAREN OVSEJEVI Cátedra de Bioquímica, Departamento de Biociencias, Facultad de Química, Universidad de la República, Montevideo, Uruguay JOSE M. PALOMO Institute of Catalysis, CSIC, CAMPUS UAM-Cantoblanco, MARTA PASTOR NanoBioCel Group, Laboratory of Pharmaceutics, School of Pharmacy, University of the Basque Country, Vitoria-Gasteiz, Spain ; Networking Biomedical Research Center on Bioengineering, Biomaterials and Nanomedicine, CIBER-BBN, Vitoria-Gasteiz, Spain JOSÉ LUIS PEDRAZ NanoBioCel Group, Laboratory of Pharmaceutics, School of Pharmacy, University of the Basque Country (UPV/EHU), Vitoria-Gasteiz, Spain BEATRIZ PELAZ Nanotherapy and Nanodiagnostics Group (GN2), Campus Rio Ebro, Instituto de Nanociencia de Aragón, Universidad de Zaragoza, Zaragoza, Spain PABLO DEL PINO Nanotherapy and Nanodiagnostics Group (GN2), Campus Rio Ebro, Instituto de Nanociencia de Aragón, Universidad de Zaragoza, Zaragoza, Spain ESTER POLO Nanotherapy and Nanodiagnostics Group (GN2), Instituto de Nanociencia de Aragón (INA), Universidad de Zaragoza, Zaragoza, Spain SARA PUERTAS Nanotherapy and Nanodiagnostics Group (GN2), Instituto de Nanociencia de Aragón (INA), Universidad de Zaragoza, Zaragoza, Spain MANFRED T. REETZ Max-Planck-Institut fur Kohlenforschung, Mulheim an der Ruhr, Germany AMINA RHOUATI IMAGES EA 4218, University of Perpignan, Perpignan Cedex, France CINTIA W. RIVERO Laboratorio de Investigaciones en Biotecnología Sustentable (LIBioS), Universidad Nacional de Quilmes, Bernal, Argentina JAVIER ROCHA-MARTIN Institute of Catalysis, CSIC, CAMPUS UAM-Cantoblanco,

11 Contributors xi OSCAR ROMERO Institute of Catalysis, CSIC, CAMPUS UAM-Cantoblanco, IPSITA ROY Department of Biotechnology, National Institute of Pharmaceutical Education and Research, Punjab, India PELLO SÁNCHEZ NanoBioCel Group, Laboratory of Pharmaceutics, School of Pharmacy, University of the Basque Country, Vitoria-Gasteiz, Spain ; Networking Biomedical Research Center on Bioengineering, Biomaterials and Nanomedicine, CIBER-BBN, Vitoria-Gasteiz, Spain MERYAM SARDAR Department of Biosciences, Jamia Milia Islamia, New Delhi, India AUDREY SASSOLAS IMAGES EA, University of Perpignan, Perpignan Cedex, France VEENA SINGH Department of Chemistry, Indian Institute of Technology Delhi, New Delhi, India SUSAN R. SIZEMORE Universal Technology Corporation, Dayton, OH, USA ; Airbase Sciences Branch, Air Force Research Laboratory, Tyndall Air Force Base, Panama city, FL, USA KUSUM SOLANKI Centre for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, NY, USA GUINEVERE STRACK Oak Ridge Institute for Science and Education, Oak Ridge, TN, USA ; Airbase Sciences Branch, Air Force Research Laboratory, Tyndall Air Force Base, Panama city, FL, USA RANDI TATUM Universal Technology Corporation, Dayton, OH, USA ; Airbase Sciences Branch, Air Force Research Laboratory, Tyndall Air Force Base, Panama city, FL, USA JORGE A. TRELLES Laboratorio de Investigaciones en Biotecnología Sustentable (LIBioS), Universidad Nacional de Quilmes, Bernal, Argentina