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ENZYME ENGINEERING
Volume 5
A Continuation Order Plan is available for this series. A continuation order will bring delivery of each new volume immediately upon publication. Volumes are billed only upon actual shipment. For further information please contact the publisher.
ENZYME ENGI NEERING Volume 5
Edited by
Howard H. Weetall Corning Glass Works Corning, New York
and
Garfield P. Royer The Ohio State University Columbus, Ohio
PLENUM PRESS · NEW YORK AND LONDON
The Library of Congress cataloged the second volume of this title as follows:
Engineering Foundation Conference on Enzyme Engineering, 2d, Henniker, N. H., 1973. Enzyme engineering; [papers] Edited by E. Kendall Pye and Lemuel B. Wingard, Jr.
New York, Plenum Press [1974]
Called volume 2 in continuation of a volume with the same title published in 1972, which contains the papers of the 1 st Engineering Foundation Conference on Enzyme Engineering.
1. Enzymes - Industrial applications - Congresses. I. Pye, E. Kendall, ed. II. Wingard, L., ed. III. Title. [DNLM: 1. Biomedical engineering - Congresses. 2. En· zymes - Congresses. W3 EN696] TP248.E5E53 1973
ISBN-13: 978-1-4684-3751-5 DOl: 10.1007/978-1-4684-3749-2
660'.63 74·13768
e-ISBN-13: 978-1-4684-3749-2
Proceedings of the Fifth International Enzyme Engineering Conference, held in Henniker, New Hampshire, July 29-August 3,1979.
© 1980 Plenum Press, New York A Division of Plenum Publishing Corporation 227 West 17th Street, New York, N.Y. 10011
Softcover reprint of the hardcover 1st edition 1980
All rights reserved
No part of this book may be reproduced, stored in a retrievai system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher
ORGANIZATION OF THE CONFERENCE
SPONSOR:
The Engineering Foundation 345 East 47th Street New York, N.Y. 10017 U.S.A.
EXECUTIVE COMt:lITTEE:
Howard H. Weeta11. Garfield P. Royer. Lemuel B. Wingard, Jr. Sanford S. Cole. Ichiro Chibata Peter Dunni11. .
ADVISORY BOARD
1. Berezin G. Broun C. Colton D. Fink S. Fukui W. Hornby J. Konecny M. Lilly G. Manecke A. Marconi A. Michaels K. Mosbach
v
Executive Chairman Program Chairman Permanent Member Conference Director Member Member
K. Pye D. Ryu H. Samejima G. Schmidt-Kastner B. Schneider H. Tenoso D. Thomas K. Venkatasubramanian F. Voss M. Weibel o. Zaborsky
vi ORGANIZATION OF THE CONFERENCE
ORGANIZATION OF THE CONFERENCE (CONT'D)
PROGRAM COMMITTEE:
I. Berezin A. Laskin G. Broun G. Manecke R. Chambers G. Royer D. Fink S. Suzuki L. Goldstein W. Veith C. Horvath H. Weetall M. Kula
FINANCIAL CONTRIBUTORS
To The Fifth International Enzyme Engineering Conference
The major contribution received was from:
NOVO Industries, AG
We also received liberal support from the following firms.
Abbott Laboratories Anheuser-Busch Bayer, AG Ciba-Geigy, Ltd. Dow Chemical Company Kraft, Inc. Pfizer, Inc. AHa Laval Astro Lakemidell Boehringer Mannheim, GmbH Corning Glass Works Japanese Society of Enzyme Engineering Miles Laboratories SNAM Progetti, SPA
NEXT ENZYME ENGINEERING CONFERENCE
FALL 1981: Enzyme Engineering VI tentatively
scheduled for September 20 - 25,
1981 at the Hotel Shima Kanko,
Kashikojima, Japan
EXECUTIVE COMMITTEE:
Saburo Fukui. .
Ichiro Chibata.
David Fink.
Jan Konecny
Garfield Royer.
Howard Weetall.
Michael Weibel.
Lemuel Winga~d, Jr.
Sanford Cole. .
vii
Executive Chairman
Program Chairman
U.S.A. Member
European Member
U.S.A. Member
U.S.A. Member
U. S .A. Member
Permanent Member
Conference Director
WORKSHOPS HELD AT EE V
During the five days of the conference, a series of workshops were held for the participants. These workshops were as follows:
Chemistry of Immobilization (L. Goldstein and G. Manecke, Chairmen)
Enzymes in Organic Synthesis (J. Konecny and H. Samejima, Chairmen)
Biomedical Applications: Enzyme Stabilization and Therapy (T. Chan?, and L. Wingard, Jr., Chairmen)
Analytical Applications (B. Mattiasson, Chairman)
Kinetics and Reactor Design (W. Vieth and D. Thomas, Chairmen)
viii
PREFACE
Enzyme technology continues to maintain a high degree of interest both in the academic and industrial communities. Since the last Enzyme Engineering Conference held in Bad Neuenahr, Federal Republic of Germany, two years ago, an increasing emphasis has been placed on the study and application of immobilized whole cells and organelles. This new emphasis has been reflected in the number of presentations directed to this area.
The Fifth International Enzyme Engineering Conference was held in Henniker, New Hampshire, July 29 to August 3, 1979. The organizers of this conference are especially grateful for the generous support received from a number of industrial organizations.
The conference was attended by 183 participants representing over 22 countries making this truly an international conference.
During this conference, emphasis was placed on a wide variety of areas including: enzyme production, energy transduction, cofactor modification, biomass conversion, immobilized enzymes, cells and organelles, and enzymatic synthesis of chemicals and pharmaceuticals.
This volume contains most of the presentations and posters presented at the Fifth Conference. The names of the session cochairmen, workshop chairmen, committee members and sponsoring organizations are included as an appreciation of their efforts in making this a successful conference.
The preparation of this volume was carried out by the editors including editing and proofing of the individual manuscripts and the final copy of this volume. The editors are indebted to Ms. S. Harrau of Corning Glass Works, Biomedical Research Department, for her job in retyping and proofreading all the manuscripts and putting them in their final form for reproduction by the publisher.
ix
x PREFACE
Our special thanks go to Mr. Sanford Cole of the Engineering Foundation without whose help this conference could not have taken place.
Howard H. Wee tall Garfield P. Royer
March, 1980
CONTENTS
KEYNOTE PAPER . . 1
Achievements and Predicted Developments in Enzyme Engineering. 3
E. Katcha1ski-Katzir
SESSION I. ENZYME PRODUCTION 31 Chairmen: R. Kula and M. Weibel
Comparative Quantitative Physiology of High Cellulase 33 Producing Strains of Trichoderma Reesei
D. D. Y. Ryu, R. Andreotti, J.Medeiros and M. Mande1s
Bacterial Exo-Enzyme and Exo-Toxin Export. . . . 41 E. A. Pepper, J. Melling and R. C. W. Berkeley
Enzyme Purification by Liquid-Liquid Extraction. 45 H. Hustedt, K. H. Kroner, U. Menge and M.-R. Kula
Continuous Isolation of Yeast-Lytic Enzymes from Citophaga. . . . • • . . • . . . . . • • • 49
J. A. Asenjo
Characterization of Membranes for Enzyme Retention • 57 E. F1asche1
Cloning of the Penicillin G-Acy1ase Gene of Escherichia coli ATCC 11105 on Mu1ticopy P1asmids. 61
H. Mayer, J. Collins and F. Wagner
Immobilized Tannin as Protein Adsorbent-Preparation, Characteristics, and Applications. • . • . . . 71
I. Chibata, T. Tosa, T. Mori and T. Watanabe
Aminoa1ky1po1ysaccharide Sorbents in Purification of Enzymes. • . . . . . . . . . . . • • . . . . • . • • 75
G. B. Gerasimiene, A. A. G1emza, D. A. Kazlauskas, D. P. Karpaviciene, V. V. Ku1iene
xi
CONTENTS
Immunochemical Identification of a New Thermostable S-galactosidase from a Bacillus Species • • . . . . • 79
M. Schulein
Mass Spectrometer Monitoring of a Yeast Fermentation. 85 J. C. Weaver, C. R. Perley and C. L. Cooney
Affinity Chromatographic Investigations on Enzyme Coenzyme Complexes of CoA-Dependent Enzymes • . . 89
B. Limbach and H. -L. Schmidt
SESSION II. ENZYMES AND ENERGY TRANSDUCTION .•.. 93 Chairmen: I. V. Berezin and S. Suzuki
Principles of Bioelectrocatalysis 95 I. V. Berezin, S. D. Varfolomeev and M. V. Lomonosov
Cofactor Modified Electrodes for Energy Transfer. .• 101 L.B. Wingard, Jr.
Immobilized Thylakoids and Chromatophores: Hydrogen Production and ATP Regeneration . • .
V. Larreta Garde, M. F. Cocquempot, J. N. Barbotin, B. Thomasset and D. Thomas •....
Some Aspects of Direct Bioelectrocatalytic Regeneration of Cofactors . . • • . • • . •
I. V. Osipov, S. D. Varfolomeev
A New Enzyme Transducer Combination: The Enzyme
109
119
Transistor. . . . . . • • . . . 123 B. Danielsson, K. Mosbach, I. Lundstrom, L. Stiblert
A Simple, General Method for Preparation of Hydro-Soluble Polymeric Adenine Nucleotide Coenzymes. 127
F. Le Goffic, S. Sicsic and C. Vincent
Cofactor Reaction-Diffusion Kinetics for an Alcohol Dehydrogenase Membrane. . . • . . . . • • • • 133
L. B. Wingard, Jr. and J. R. Millis
Approaches to Stabilization of Hydrogenase and Nitrogenase Against Oxygen Inactivation . . . • 135
A. M. Klibanov, N. O. Kaplan and M. D. Kamen
CON~N~ •
Biochemical Energy Conversion System. . • . . . . • 143 S. Suzuki, I. Karube, T. Matsunaga and H. Kayano
SESSION III: BIOMASS CONVERSION . 147 Chairman: G. Tsao
Utilization of B-Glucosidase from Aspergillus Species in the Hydrolysis of Cellulose. • • . • . . . . • •• 149
P. M. A. Nybergh and M. J. Bailey
The Comparative Role of Exoglucosidase and Cellobiase in Glucose Formation from Cellulose . . . • .. 153
A. A. Klyosov, A. P. Sinitsyn and M. L. Rabinowitch
Novel Enzymes from Methylotrophic Microorganisms. 167 A. I. Laskin, C. T. Hou and R. N. Patel
Ethanol - Butanediol Fermentation of Xylose 171 S. Veeraraghavan, Y. Y. Lee, R. P. Chambers, T. A. McCaskey
Fluorimetric Monitoring of Methanogenesis in'Anaerobic Digesters . . • • . . • . . . . . . . . . • 175
E. J. Nyns, H. P. Naveau and M. J. Delafontaine
SESSION IV: BIOMEDICAL AND ANALYTICAL APPLICATIONS OF ENZYMES AND ANTIBODIES ....
Chairmen: M. Wilchek and P. Carr
Enzyme Channelling Immunoassay. Enzyme Immunoassay Technique. .
E. F. Ullman and D. J. Litman
A New Homogeneous
Human Renal Renin: Purification, Production of
177
179
Specific Antibodies. Clinical Applications • . 187 F. X. Galen, C. Devaux, P. Sicard, T. Guyene, J. Bariety, J. Menard and P. Corvol
Competitive Binding Studies of Carbohydrate-Lectin Interactions Using a Lectin Electrode . . . • . . . 193
C. Borrebaeck and B. Mattiasson
Potentiometric Enzymatic Measurement of Glucose: Possible In Vivo Use. . . . . . . . . . . . . . 197 ---L. B. Wingard, Jr., S. K. Wolfson, Jr., C. C. Liu,
S. J. Yao, J. G. Schiller and A. L. Drash
xiv CONTENTS
Immobilized Enzyme Pipette - "Impette". • • • . . •• 201 P. V. Sundaram
Electrochemical Determination of Lipids in Serum. •. 205 S. Suzuki and I. Karube
Immobilized Enzymes for Medical Application . . 209 E. I. Chazov, V. N. Smirnov, V. P. Torchilin, I. M. Tereshin, B. V. Moskvichev
Photoenzography: Using Enzymes for Photographic Aims. . . . . . .
N. F. Kazanskaya
The Design of Peroxide Enzyme Membrane Polarographic
213
Sensors for Clinical and Industrial Analysis. • . 217 T. A. Grooms, L. C. Clark, Jr. and B. J. Weiner
New Approaches Using Immobilized Enzymes for the Removal of Urea and Ammonia . . • . . • . . • . . 225
T. M. S. Chang
Enzyme-Collagen Reactor Designed from an Hemodialysis Module. . • . • . . •. ...••.••••••. 231
P. R. Coulet, F. Paul, D. Dupret and D. C. Gautheron
Immobilization and Characterization of Enzymes on Hollow Fibers for a Possible Use in the Biomedical Field . . . . . . • . . • . . • • . . • 235
P. G. Pietta, D. Agnellini, G. Mazzola, G. Vecchio, S. Colombi and G. Bianchi
Magnetic Microspheres for Targeting of Drugs. . . •• 239 K. Mosbach and U. Schroder
Modification of Enzymes with Water-Soluble Polymers . 243 I. M. Tereshin and B. V. Moskvichev
Detoxication of Ammonia by Immobilized Urea Cycle Enzymes . . • . • •. ...•. •....• 247
Y. Miura, H. Urabe, K. Miyamoto and M. Okazaki
Use of the Enzyme Thermistor for Continuous Monitoring and Control in Biotechnology. • . • . • • • . . 251
B. Mattiasson, B. Danielsson and F. Winquist
Distribution of Damkohler Number of Spherical Matrix Particles by Image Analysis
M. Sernetz, M. Chun, R. Kindt and B. Gelleri 255
CONTENTS
On-line Determination of Reaction Rate Versus Substrate Concentration for an Enzymatically Catalysed Reaction by Means of a Microcomputer System. • • • .•• • • • • • • • • • • • •
R. Wichmann and C. Wandrey
Microbial Sensors for Ethyl Alcohol, Acetic Acid and Ammonia • • • •
I. Karube and S. Suzuki
SESSION V: LARGE-SCALE TRANSFORMATIONS USING BOUND ENZYMES. • • • • • • .• ••••• •
Chairmen: H. Samejima and W. Pitcher
xv
259
263
267
Improved Whey Treatment by Immobilized Lactase. 269 W. Marconi, F. Bartoli, F. Morisi and A. Mariani
Lactose Hydrolysis by Immobilized Lactase: Semi-industrial Experience • • • • . • • 279
L. A. Dohan, J. L. Baret, S. Pain and P. Delalande
Production of Useful Nucleotides with Immobilized Microbial Cells .• ••• • •• •••••• 295
Y. Ado, K. Kimura and H. Samejima
Heterogeneous Biocatalysis in the Degradation of S-Glucan Polymers • • . • . • • • • • • 305
P. Linko and Y. Y. Linko
Absorption Into a Liquid Film in Laminar Flow Coupled with an Enzyme Catalyzed Reaction at the Solid Surface 309
J. E. Prenosil, T. Buhlmann and H. Pedersen
Catalyst Deactivation and Optimal Operation Policy: Immobilized S-galactosidase • • • • • • • • • • • • • 317
J. E. Prenosil, J. Peter and J. R. Bourne
Stability Studies on the Immobilized Glucose Oxidase/ Catalase Enzyme System. • • . • . • . • • • • • 321
R. S. Carter, J. E. Prenosil and J. R. Bourne
Hydrodynamics and Reactors .••••
J. M. Engasser, M. Garnier
Kinetics of Hollow Fiber Enzyme
J. Caumon, A. Marc, J. Lede and 325
Isomerose Syrups Containing Greater than 90% Fructose 329 S. A. Barker, H. A. Bowes and P. J. Somers
xvi
SESSION VI: IMMOBILIZED CELLS AND ORGANELLES •• Chairmen: S. Fukui and I. Chibata
CONTENTS
333
Inunobilization of Whole Hicrobial Cells for the Production of 6-Amino Penicillanic Acid 335
J. Klein and F. Wagner
Application of Inunobilized Biocatalysts to Bio-conversion in Hydrophobic Conditions. . . . . 347
S. Fukui, T. Ornata, T. Yamane and A. Tanaka
Alginate Bead Entrapped Yeast Cells for Continuous Inversion of Sucrose and Holasses • • . • • . 355
Y. Y. Linko, L. Weckstrom and P. Linko
Physical Characterization of Biocatalyst Particles Obtained form Polymer Entrapment of Whole Cells 359
J. Klein, P. Washausen, H. Kluge and H. Eng
The Use of Free and Inunobilized Cells in the Presence of Organic Solvents: The Oxidation of Cholesterol by Nocardia Rhodochrous • . . . . . . . . . .. 363
J. H. C. Duarte and H. D. Lilly
Properties of Enzymes Solubilized in Hydrocarbons via Reversed Hicelles . . . . . . . . . . 369
P. Luisi, P. Heyer and R. Wolf
The Potential Use of Inunobilized Plant Cells for the Production and Transformation of Natural Products . 373
P. Brodelius, B. Deus, K. Hosbach and H. H. Zenk
Inunobilized Whole Cells of the Yeast Trigonopsis variabilis Containing D-Amino Acid Oxidase for the Production of a.-Keto Acids. .....•.... 383
P. Brodelius, B. Hagerdal and K. Hosbach
Enzymatic Synthesis of Pantothenic Acid by Escherichia coli Cells. . • . . • . . • . . . . . . .. 389
Y. Kawabata and A. L. Demain
Production of Useful Chemicals Using Cells Inunobilized with Polyacrylamide and Carrageenan . . • • . . • •. 393
I. Chibata
Affinity Chromatographic Purification of Proteins Using lnunobilized Cells . • . • . • . . . . 401
B. Hattiasson and H. Ramstorp
CONTENTS
Synthesis of Coenzymes by Immobilized Cell System H. Yamada, S. Shimizu, Y. Tani and T. Hino
SESSION VII: BOUND ENZYMES AND THE SYNTHESIS OF FINE CHEMICALS AND PHARMACEUTICALS •••••
Chairmen: J. Konecny and K. Mosbach
xvii
405
414
Continuous Deacetylation of Cephalosporins. • • 415 J. Konecny and M. Sieber
Thermostability of Soluble and Immobilized Subtilisins After Their Modification by Dextrans and Dextrins • • 423
L. A. Nakhapetyan and V. Kh. Akparov
Isolation and Immobilization of Porcine Ligandin with Glutathione Transferase Activity • • • • • • 427
L. Callegaro and A. Fontana
Studies on the Stability of Soluble and Immobilized Alcohol Dehydrogenase from Yeast Mitochondria 431
M. J. Brougham and D. B. Johnson
Distribution of Staphylococcal Nuclease Insolublizied on Sepharose. • . • • • • • • • • • • 435
J. M. Guisan, V. M. Fernandez and A. Ballesteros
Immobilized Penicillin Acylase for Production of 6-APA From Penicillin-V. • • • • • • • • • • • • . ..• •• 439
S. Gestrelius
Preparation and Characterization of Metal Oxide-coated Supports for Oxidase Enzymes • • • •
B. R. Allen and D. J. Fink
~nzyme Immobilization on Pyridine Containing Polymers. • • • • • • • • • • • • • • • •
F. Pittner, T. Miron, G. Pittner and M. Wilchek
Cross-linked Pectate. • M. A. Vijayalakshmi, D. Picque and G. B. Broun
Immobilization of Biocatalysts Using Ultrafiltration
443
447
451
Techniques. • • • • • • • • • • • • • • • • • • 453 C. Wandrey, R. Wichmann, A. F. Bueckmann and M. R. Kula
xviii CONTENTS
B-Galactosidase Immobilized on BenzoquinoneActivated Bead Cellulose and on Oxirane-Acrylic Beads .• •..•.....•..•••.. 457
M. Chun and M. Sernetz
Application of Immobilized Carboxypeptidase Y for Deblocking in Peptide Synthesis . . . • . . . . . 461
G. P. Royer, H. Y. Hsiao and G. M. Anantharamaiah
Adsorption and Distribution of Enzymes in Carriers. 465 K. Buchholz, S. K. Duggal and A. Borchert
Application of Photosensitive Immobilized aChymotrypsin to Synthetic Reaction. . . .
I. Karube and S. Suzuki
APPENDIX
List of Participants.
Subject Index • . . •
469
473
483
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