PQQ and Quinoproteins: Proceedings of the First International Symposium on PQQ and Quinoproteins, Delft, The Netherlands, 1988

365 Pages·1989·12.28 MB·English

by  C. Anthony (auth.), J. A. Jongejan, J. A. Duine (eds.)

PQQ AND QUINOPROTEINS
PQQ and Quinoproteins
Proceedings o/the First International Symposium on PQQ and Quinoproteins,
Delft, The Netherlands, 1988
edited by
J. A. JONGEJAN and J. A. DUINE
Biotechnology Centre.
Delft University of Technology,
Delft, The Netherlands
KLUWER ACf.DEMIC PUBLISHERS
DORDRECHT / BOSTON / LONDON
Library of Congress Cataloging in Publication Data
International Symposium on POO and Ouinoproteins (1st: 1988 : Delft,
Netherlands)
P 0 0 quinoproteins : proceedings of the First International
Symposium and POO and Ouinoprotein, Delft, the Netherlands, 1988
edited by J.A. Jongejan and J.A. Duine.
p. CII.
Includes indexes.
1. POO (Biochemistry)--Congresses. 2. Ouinoproteins--Congresses.
I. Jongejan, J. A., 1944- II. Duine, J. A. III. Title.
OP801.P654I67 1988
574. 19'25--dc20 89-7956
ISBN-13: 978-94-0 I 0-6920-5 e-ISBN-13: 978-94-009-0957-1
DOl: 10.1007/978-94-009-0957-1
Published by Kluwer Academic Publishers,
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Softcover reprint of the hardcover 1s t edition 1989
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No part of the material protected by this copyright notice may be reproduced or
utilized in any form or by any means, electronic or mechanical
including photocopying, recording or by any information storage and
retrieval system, without written permission from the copyright owner.
The first international Symposium on PQQ and Quinoproteins was held in
Delft from 5-7 September, 1988. It attracted over 100 participants from
many countries, from universities as well as industrial companies. In view
of the late announcement, this is a surprising large number. Also the
enthousiasm with which the proposal was received to make preparations for
ISQ-2 (most probably to be held in Japan), gave the impression that there
exists a need for symposia specially devoted to this topic.
The initiative is indeed justified in the light of the growing
importance of this novel field of enzymology. While originally
quinoproteins seemed restricted to some specialised microbes, nowadays it
appears that for many well known mammalian enzymes which once were thought
to be simple metalloproteins or pyridoxoproteins (enzymes containing
pyridoxal phosphate), PQQ functions as a cofactor. Since the large part of
these enzymes are involved in the degradation or biosynthesis of
bioregulators, it is already clear that an impact can be expected in the
field of pharmacology and nutrition. First indications for this can
already be found in this volume, presenting the formal presentations,
either as a lecture or as a poster, given during the symposium. Also the
variety of contributions nicely reflects the involvement of several
different disciplines in this topic.
May ISQ-1 form the beginning of a long standing tradition.
October, 1988 J.A. Duine.
Delft.
The organizing Committee wishes to acknowledge the following companies for
their financial aid:
Fluka Chemie, Buchs, Switzerland
Ciba-Geigy, Basel, Switzerland
Hoffmann-La Roche, Basel, Switzerland
Boehringer Mannheim, Mannheim, FRG
Unilever Research Laboratories, Vlaardingen, The Netherlands
Merrell Dow, Strasbourg, France
Gist-Brocades, Delft, The Netherlands
Andeno, Venlo, The Netherlands
Hewlett Packard Nederland, Amstelveen, The Netherlands
Sandoz, Basel, Switzerland
AVEBE, Veendam, The Netherlands
TABLE OF CONTENTS
Section: ALCOHOL AND ALDEHYDE DEHYDROGENASES
QUINOPROTEINS IN C 1 -DISSIMILATION BY BACTERIA
C. Anthony ........................... . . . . . .. 1
METHANOL DEHYDROGENASE: MECHANISM OF ACTION
J. Frank, M. Dijkstra, C. Balny, P.E.J. Verwiel and J.A. Duine ..... 13
QUINOPROTEIN ETHANOL DEHYDROGENASE FROM PSEUDOMONAS
H. Gorisch and M. Rupp ........................... 23
PQQ-DEPENDENT METHANOL DEHYDROGENASE FROM
CLOSTRIDIUM THERMOA UTOTROPHICUM
D.K. Winters and L.G. Ljungdahl .......... . . ... 35
NEW PQQ-ENZYME: AROMATIC ALCOHOL AND ALDEHYDE
DEHYDROGENASES IN RHODOPSEUDOMONAS ACIDOPHlLA M402
K. Yamanaka . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40
STRUCTURAL STUDIES ON THE PQQ-LIKE COFACTOR OF
NITROALKANE OXIDASE FROM FUSARIUM OXYSPORUM
K. Tanizawa, T. Moriya, T. Kido, H. Tanaka and K. Soda . . . . . 43
REGULATION OF METHANOL DEHYDROGENASE SYNTHESIS IN
PARA COCCUS DENITRIFlCANS
N. Harms, R.J.M. van Spanning, L.F. Oltmann and A.H. Stouthamer . 46
METHANOL DEHYDROGENASE FROM NOCARDIA SP.239
P.W. van Ophem and J.A. Duine ....................... 50
PROPERTIES OF DYE-LINKED FORMALDEHYDE DEHYDROGENASE
FROM HYPHOMICROBIUM ZV 580 GROWN ON METHYLAMINE
F.P. Kesseler, I. Baduns and A.C. Schwartz ................ 54
viii
Section: GLUCOSE DEHYDROGENASES
PHYSIOLOGICAL SIGNIFICANCE AND BIOENERGETIC ASPECTS OF
GLUCOSE DEHYDROGENASE
O.M. Neijssel, R.W.j. Hommes, P.W. Postma and D.W. Tempest S7
QUINOPROTEIN D-GLUCOSE DEHYDROGENASES IN
ACINETOBACTER CALCOACETICUS LMD 79.41 : PURIFICATION AND
CHARACTERIZATION OF THE MEMBRANE-BOUND ENZYME
DISTINCT FROM THE SOLUBLE ENZYME
K. Matsushita, E. Shinagawa, O. Adachi and M. Ameyama ....... 69
CLONING OF THE GENES ENCODING THE TWO DIFFERENT GLUCOSE
DEHYDROGENASES FROM ACINETOBACTER CALCOACETICUS
A.-M. Cleton-jansen, N. Goosen, K. Vink and P. van de Putte .... 79
INVESTIGATIONS ON THE ACTIVE SITE OF GLUCOSE
DEHYDROGENASE FROM PSEUDOMONAS FLUORESCENS
Y. Imanaga ....................... . . ..... 87
PRODUCTION OF GLUCONIC AND GALACTONIC ACIDS FROM WHEY
N. van Huynh, M. Decleire, j.C. Motte and X. Monseur . . ... 97
MODE OF BINDING OF PYRROLOQUINOLINE QUINONE TO
GLUCOSE DEHYDROGENASE FROM ACINETOBACTER CALCOACETICUS
H. Gorisch, O. Geiger and M. Adler ................... 100
GLUCOSE DEHYDROGENASE FROM ZYMOMONAS MOBILIS:
EVIDENCE FOR A QUINOPROTEIN
M. Strohdeicher, S. Bringer-Meyer, B. Neu!3, R.A. van der Meer,
j.A. Duine and H. Sahm . . . . . . . . . . . . . . . . . . . . . . . . . 103
HAEM-CONTAINING PROTEIN COMPLEXES OF ACINETOBACTER
CALCOACETICUS AS SECONDARY ELECTRON ACCEPTORS FOR
QUINOPROTEIN GLUCOSE DEHYDROGENASE
A. Geerlof, P. Dokter, j.E. van Wielink and j.A. Duine ......... 106
Section: ANALYSIS OF PQQ
IDENTIFICATION AND QUANTIFICATION OF PQQ
R.A. van der Meer, j.A. Jongejan and j.A. Duine . . . . . . . . . . . . 111
ix
GAS CHROMATOGRAPHY OF PQQ
O. Suzuki, T. Kumazawa, H. Seno, T. Matsumoto and T. Urakami .. 123
DIRECT AND AMPLIFIED REDOX-CYCLING MEASUREMENTS OF PQQ
IN QUINOPROTEINS AND BIOLOGICAL FLUIDS:
PQQ-PEPTIDES IN PRONASE DIGESTS OF DBH AND DAO
M.A. Paz, R. Fliickiger, E. Henson and P.M. Gallop .......... 131
BINDING OF PYRROLOQUINOLINE QUINONE TO SERUM ALBUMIN
O. Adachi, E. Shinagawa, K. Matsushita, K. Nakashima, K. Takimoto
and M. Ameyama ................................ 145
Section: PHYSIOLOGICAL EFFECTS OF PQQ
GROWTH STIMULATING EFFECT OF PYRROLOQUINOLINE QUINONE
FOR MICROORGANISMS
M. Ameyama .......................... . 149
NUTRITIONAL ESSENTIALITY OF PYRROLOQUINOLINE QUINONE
R. Rucker, ]. Killgore, L. Duich, N. Romero-Chapman, C. Smidt
and D. Tinker .................................. 1 S9
EFFECTS OF EXOGENOUS PQQ ON MORTALITY RATE AND SOME
BIOCHEMICAL PARAMETERS DURING ENDOTOXIN SHOCK IN RATS
T. Matsumoto, O. Suzuki, H. Hayakawa, S. Ogiso, N. Hayakawa,
Y. Nimura, I. Takahashi and S. Shionoya . . . . . . . . . . . . . . . . . 162
Section: PQQ PRODUCTION
THEORETICAL EVALUATION OF LARGE SCALE PRODUCTION OF PQQ
VIA FERMENTATION
B.]. Wesselink and P. Gupta ......................... 165
Section: BIOSYNTHESIS OF PQQ
GENES INVOLVED IN THE BIOSYNTHESIS OF PQQ FROM
ACINETOBACTER CALCOACETICUS
N. Goosen, H.P.A. Horsman, R.G.M. Huinen, A. de Groot
and P. van de Putte .............................. 169
x
PQQ: BIOSYNTHETIC STUDIES IN METHYLOBACTERIUM AM1 AND
HYPHOMICROBIUM X USING SPECIFIC 13C LABELING AND NMR
D.R. Houck, J.L. Hanners, C.J. Unkefer, M.A.G. van Kleef
and J.A. Duine ................................. 177
THE ROLE OF PQQ IN K. AEROGENES AND CLONING OF PQQ GENES
J.J.M. Meulenberg, W.A.M. Loenen, E. Sellink and P.W. Postma ... 187
MUTANTS OF METHYLOBACTERIUM ORGANOPHILUM
UNABLE TO SYNTHESIZE PQQ
F. Biville, P. Mazodier, E. Turlin and F. Gasser ............. 190
Section: REACTIVITY OF PQQ
THE CHEMISTRY AND B10MIMETICS OF PQQ
Y. Ohshiro and S. Itoh ............................ 195
STRUCTURAL PROPERTIES OF PQQ INVOLVED IN THE ACTIVITY OF
QUINOHAEMOPROTEIN ALCOHOL DEHYDROGENASE FROM
PSEUDOMONAS TESTOSTERONI
J.A. Jongejan, B.W. Groen and J.A. Duine ................. 205
FACTORS RELEVANT IN THE REACTION OF PQQ WITH AMINO ACIDS
ANALYTICAL AND MECHANISTIC IMPLICATIONS
M.A.G. van Kleef, J.A. Jongejan and J.A. Duine ............. 217
INHIBITION OF COLLAGEN HYDROXYLASES BY PQQ REVEALS ITS
DOMAIN STRUCTURE
V. GUnzler, H.M. Hanauske-Abel, J.A. Duine, K.I. Kivirikko
and E.J. Corey ........................... . . . 227
REACTION OF 2,7,9-TRICARBOXY-PQQ WITH NUCLEOPHILES
W.S. McIntire ........................... . . .. 233
REACTION OF PQQ AND ITS ANALOGUES WITH NADH;
APPLICATION TO THE HLADH-CATALYZED OXIDATION OF ALCOHOLS
S. Itoh, M. Kinugawa and Y. Ohshiro ................... 236
CHEMICAL BEHAVIOUR OF COENZYME PQQ TOWARD
AMINE HOMOLOGS
Y. Ohshiro, M. Mure, K. Nii and S. Itoh. . . . . . . . . . . . . . . .. 239
xi
Section: STRUCTURAL STUDIES ON PQQ
THE THREE-DIMENSIONAL STRUCTURE OF PQQ
AND RELATED COMPOUNDS
H. van Koningsveld, J.A. Jongejan and J.A. Duine ............ 243
COPPER(II) COMPLEXES CONTAINING REDUCED PQQ AS A MODEL
FOR THE ACTIVE SITE OF COPPER-REQUIRING AMINE OXIDASE
S. Suzuki, T. Sakurai, S. Itoh and Y. Ohshiro .............. 253
13C AND lH-NMR STUDIES OF PQQ AND SELECTED DERIVATIVES
D.R Houck and C.J. Unkefer ........................ 256
Section: METHYLAMINE DEHYDROGENASES
MECHANISM OF THE METHYLAMINE DEHYDROGENASE
REDUCTIVE HALF REACTION
RB. McWhirter and M.H. Klapper ..................... 259
ELECTRON TRANSPORT FROM METHYLAMINE TO OXYGEN IN THE
GRAM-NEGA TIVE BACTERIUM THIOBACILLUS VERSUTUS
J.E. van Wielink, J. Frank Jzn and J.A. Duine .............. 269
Section: AMINE OXIDASES
COPPER-CONTAINING AMINE OXIDASES
A. Finazzi-Agro . . . . . . . . . . . . . . . . . 279
ACTIVE SITE STRUCTURES OF COPPER-CONTAINING OXIDASES
P.F. Knowles, I. Singh and K.D.S. Yadav, F.E. Mabbs, D. Collison,
C.E. Cote, D.M. Dooley and M.A. McGuirl ................ 283
ON THE ROLE OF COPPER IN PQQ AMINE OXIDASES
B. Mondovi and P. Riccio ........... . . ..... 289
MECHANISTIC PROBES OF COPPER AMINE OXIDASES
J.P. Klinman, C. Hartmann and S.M. Janes ...... . . ...... 297
COPPER-PQQ INTERACTIONS IN AMINE OXIDASES
D.M. Dooley, C.E. Cote, M.A. McGuirl, J.L. Bates, J.B. Perkins,
RS. Moog, I. Singh, P.F. Knowles and W.C. McIntire . . . . . . . . . 307