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Microbial Transformation of Tetralin

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Microbial Transformation of Tetralin Microbial transformation of tetralin CENTRALE LANDBOUWCATALOGUS 0000 0513 4818 Promotor: dr. ir. J. A. M. de Bont hoogleraar in de industriele microbiologic Co-promotor: dr. B. Poolman universitair docenti nd emicrobiologic ,Rijksuniversitei t Groningen rJrJO&^y, io^C• c/> Jan Sikkema Microbial transformation of tetralin Proefschrift ter verkrijging van de graad van doctor in de landbouw- en milieuwetenschappen op gezag van de rector magnificus, Dr. H. C. van der Plas, in het openbaar te verdedigen op maandag 24 mei 1993 des namiddags te vier uur in de Aula van de Landbouwuniversiteit te Wageningen. ,, O v- BIBLIOTHEEW LANDBOUWUNIVERSHEH WAC;ENINGEM ISBN 90-5485-125-2 Omslagontwerp: Anne Hof OanHeit en Mem FoarAnne VOORWOORD Het proefschrift zoals dat voor U ligt is tot stand gekomen door de inbreng van een groot aantal personen, waarvan ik er een aantal met name wil bedanken. Jan de Bont, door de vrijheid diej e me hebt geboden, maar vooral ook door jouw kritische blik heb ik heel veel geleerd. Bert Poolman, voor het meedenken over proeven en resultaten, jouw nauwgezette korrekties van de manuscripten en de prettige samenwerking. Wil Konings,d emogelijkhei d omo pjou wtransport-lab aan de toxische effecten van koolwaterstoffen te werken heeft mijn onderzoek een enorme impuls gegeven. Mark Smith,jou w kennis en enthousiasme op het gebied van aromaatmetabolisme inbacterie n waren eenbelangrijk e stimulansvoo r het uitpluizen van deafbraa k van tetralien. Mijn labmaatjes bij Industriele Microbiologic en Proceskunde in Wageningen en Moleculaire Microbiologic in Groningen voor de goede raad, discussies, buffers, fermentoren, adviezen, COV's, belangstelling, schuine buizen, kritiek, hulp, flexibiliteit, Loburg, enz., enz. Kortom, voor de goede sfeer. Marian Vermue voor de goede samenwerking in het kader van het P.C.I.B. project "Hydroxyleringva n aromaten tot geur- en smaakstoffen". Kirsten Zagt, Tini Lootsma, Ferry Sommerdijk, Frank Bastiaens, Wimva n den Heuvel, Carla Proost, Rudolf Bakker, Annette Verheul, Paul Tap, Mark Resink, Gisela Janssen en Margot Tacken dieal sonderdee lva nhu n doctoraal onderzoek hebben gewerkt aan de hydroxylering van aromaten en terpenen tot geurstoffen. Fons Peters van Quest International BV in Naarden voor het aandragen van interessante modelverbindingen enbelangstellin g voor het onderzoek.To n de Boer en Henk Schaap van de analytische afdeling van Quest, Naarden en Kees Teunis van de vakgroep Organische Chemie voor hun hulp bij de karakterisering van intermediairen. De medewerkers van de Centrale Dienst Biotechnion, met name de tekenkamer, de afdeling fotografie, en de mechanische werkplaats voor de vlotte levering en service. Finally, I would like to thank my present employer, Snow Brand E.R.L., for the time and facilities to finish my thesis. STELLINGEN 1. Deremmende werkin gva ncyclisch ekoolwaterstoffe n opd egroe iva n bacterien isme t namehe tgevol gva nophopin gva ndez everbindinge n inhe t cytoplasmamembraan. Ditproefschrif L 2. In het door Sahm et al. beschreven zuiveringsproces voor het afvalwater van pulpfabrieken wordtd eremmin gdoo rH2 S tenonrecht ebuite nbeschouwin g gelaten. Sahm, H., U. Ney, and S. M. Schoberth. 1992. Anaerobictreatmen to fwastewate rfro mth e pulpan dpape rindustry , p.431-434 .In M. R. Ladisch, andA . Bose (ed.), Harnessingbiotechnolog y forth e21s tcentury ,America nChemica lSociety ,Washington ,D.C . 3. Bij hetkweke nva nPseudomonas cepacia ATCC2935 1i nhog eceldichthede n in het door White-Stevens en Kamin beschreven medium in combinatie met salpeterzuurtitratie,word tgee nrekening gehoude nme the tvermoge nva ndez e bacterie uitnitraa the tgiftig e nitrieto pt ehopen . Berg, A.-C, O. Hoist, and B. Mattiasson. 1989.Continuou s culture with completecel l recycle:cultivatio no fPseudomonas cepacia ATCC 29351 onsalicylat efo rproductio n ofsalicylat e hydroxylase. Appl. Microbiol. Biotechnol. 30:1-4. 4. Dedoo rSchreibe re nWinkle rbeschreve nafbraa k vantetralie ndoo ree nreinkulture va n Pseudomonasstutzeri A S3 9i see ncooxidatie fproces . Schreiber, A., and U. K. Winkler. 1983. Transformation of tetralin by whole cells of Pseudomonas stutzeriA S 39. Eur.J . Appl. Microbiol. Biotechnol. 18:6-10. 5. Rapportages over de suikersamenstelling van polysachariden zonder duidelijke beschrijving vand egebruikt eisolatie -e nzuiveringsmethode n kunnen naarhe tlan dde r fabelen worden verwezen. 6. Deomschakelin gva nd ewapenindustri eo pciviel eprodukti eword tbemoeilijk t doord e geringevraa gnaa rploegscharen . 7. Koppelingva n de zuiveringsheffing aanhe twaterverbrui k zalervoo r zorgen dat men pasech twij s metwate rwordt . ko<\ f ( 8. Tenbehoev eva nd eherkenbaarhei dva nverkeerssituatie sverdien the taanbevelin g voor designalerin g vanwegwerkzaamhede nee n meerwerkelijkheidsgetrouw e afbeelding te gebraiken. 9. Hetgebrui k van hetbijvoeglij k naamwoord 'duurzame' bij begrippen zoalslandbou w en samenleving betekent dat er meerveranderin g gewenst wordt dan dit woord doet vermoeden. 10. De hoogte van de adviesprijzen voor laboratoriumapparatuur doet vermoeden dat de leveranciers uitgaanva nhe tmotto : "watee nge kervoo r geeft". Stellingenbehorend ebi jhe t proefschrift "Microbialtransformatio n of tetralin" van Jan Sikkema. Wageningen,2 4me i199 3 CONTENTS Chapter 1 GENERAL INTRODUCTION 1 Chapter 2 MEMBRANE TOXICITY OF CYCLIC HYDROCARBONS 7 Chapter 3 ISOLATION AND INITIAL CHARACTERIZATION OF BACTERIA GROWING ON TETRALIN 59 BIOCATALYTIC PRODUCTION OF HYDROXYLATED Chapter 4 AROMATIC AND ALICYCLIC COMPOUNDS: PRODUCTS DERIVED FROM TETRALIN 71 METABOLISM OF TETRALIN (1,2,3,4- Chapter 5 TETRAHYDRONAPHTHALENE) IN CORYNEBACTERIUM SP. STRAIN C125 87 EFFECTS OF THE MEMBRANE ACTION OFTETRALI N Chapter6 ON THE FUNCTIONAL AND STRUCTURAL PROPERTIES OF ARTIFICIAL AND BACTERIAL MEMBRANES 101 Chapter 7 INTERACTIONS OF CYCLIC HYDROCARBONS WITH BIOLOGICAL MEMBRANES 118 Chapter 8 CONCLUDING REMARKS 137 SUMMARY 151 SAMENVATTING 155 LIST OF ABBREVIATIONS 159 CURRICULUM VITAE 161 Chapter 1 GENERAL INTRODUCTION Since the middle of the 19th century many large scale processes for the production of commodity chemicals have been established. The procedures for the production of these commodities have been developed and optimized to highly efficient processes, which are usually performed in specially designed plants. Synthesis of fine chemicals, usually complex molecules, is often performed in laborious multi-step processes. As a result of the small product volumes, fine chemicals are manufactured in multi-purpose plants which do not provide optimal conditions for all of the catalytic steps involved. Classical chemical synthetic processes often lack specificity and selectivity and have to be performed under extreme conditions,thu shinderin gth e efficient application indirec t synthesiso f fine chemicals. Furthermore, chemical synthetic processes for the production of both commodity and fine chemicals cause serious environmental problems as a result of reagents and solvents necessary for these reactions. Therefore, present developments in organic synthesis are mainly directed at increasing the specificity and selectivity of the synthetic processes (5). This progress is stimulated by the demand for more specific drugs (21) and agrochemicals (22), and the growing awareness of environmental pollution (28). Inadditio n tochemica lsynthesis ,microorganism sprovid ehighl yspecifi ccatalysts , which have evolved over many millions of years to perform an enormous variety of chemical reactions (10,25 ,26) .Enzymati c reactions are often highly chemo-,regio - and stereoselective, have a high efficiency, and can be performed in an aqueous reaction medium under mild conditions (21). Moreover, in nature an enormous General introduction diversity of biocatalysts, which are involved in a broad spectrum of chemical reactions, is already available (9).A sa result of recent developments in molecular biology and protein engineering, the performance of enzymes canb e improved and even 'new' enzymes can be made. In addition to the selectivity and specificity, in some instances also the natural origin of biocatalysts will be advantageous. Application ofbiotransformatio n reactionsfo rth eproductio no fflavoring s mayhel p to meet the growing demand for natural products as food additives (7). Biotechnological productiono ffine chemicals . Biotechnological methods for the production of fine chemicals comprise either complete biosynthesis or biotransformation. Microbial fermentation processes employing complete biosynthetic routes are widely applied for the production of naturally occurring compounds, e.g., amino acids (1), penicillins (4). Biotransformation processes are usually restricted to a single reaction or a short sequence of reactions in order to transform defined pure compounds into defined final products. Complete biosynthesis can not be applied for the production of non-natural, synthetic chemicals. Application of enzymes to catalyze transformations of such chemicals, however, is a useful tool to perform specific organic syntheses. The essence of biotransformations can, therefore, be best described as 'chemical reactions by microorganisms or enzymes' (14). Growing cells, resting cells, permeabilized cells, crude cell extracts, or purified enzymes can be applied as biocatalysts (15). Basically, all types of enzymes (oxidoreductases, transferases, hydrolases, lyases, isomerases, and ligases) can be used as biocatalysts (10). Once a suitable biocatalyst has been identified in terms of catalyzing the
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