What makes cyclodextrin glycosyltransferase a transglycosylase Leemhuis, Reinder Johannes
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1 What makes cyclodextrin glycosyltransferase a transglycosylase Leemhuis, Reinder Johannes IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2003 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Leemhuis, R. J. (2003). What makes cyclodextrin glycosyltransferase a transglycosylase Groningen: s.n. Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date:
2 What makes cyclodextrin glycosyltransferase a transglycosylase Hans Leemhuis
3 The cover shows a maltononaose substrate (left), a maltoheptaose reaction intermediate (right) and a cyclodextrin product (lower) bound in the active site of the cyclodextrin glycosyltransferase from Bacillus circulans strain 251. The back cover shows the structure of the native enzyme. The author gratefully acknowledges support by Danisco and GBB for printing this thesis.
4 RIJKSUNIVERSITEIT GRONINGEN What makes cyclodextrin glycosyltransferase a transglycosylase Proefschrift ter verkrijging van het doctoraat in de Wiskunde en Natuurwetenschappen aan de Rijksuniversiteit Groningen op gezag van de Rector Magnificus, dr. F. Zwarts, in het openbaar te verdedigen op maandag 14 april 2003 om uur door Reinder Johannes Leemhuis geboren op 9 november 1973 te Groningen
5 Promotores: Prof. dr. L. Dijkhuizen Prof. dr. B.W. Dijkstra Beoordelingscommissie: Prof. dr. D. B. Janssen Prof. dr. A. J. M. Driessen Prof. dr. O. P. Kuipers
6 VOORWOORD Na bijna vier jaar onderzoek in het lab van Prof. Lubbert Dijkhuizen (Microbial Physiology) is het tijd om dit promotieonderzoek af te ronden door het schrijven van het voorwoord van dit proefschrift. Voor het tot stand komen van dit boekje wil ik ten eerste Lubbert bedanken voor de mogelijkheid om in zijn groep onderzoek te verrichten. Hierdoor heb ik met veel plezier een bijdrage kunnen leveren aan het ontrafelen van de reactiespecificiteit van het enzym CGTase. De jaarlijkse meetings met Danisco, te Arhus en Kopenhagen, en de discussies over CGTase die wij tijdens het reizen hadden, hebben hieraan bijgedragen. Binnen Danisco liepen de contacten via Karsten. Karsten, I thank you for the nice collaboration, and for giving me the opportunity to do fundamental research on CGTase, the enzyme of common interest. Verder wil ik Prof. Bauke Dijkstra (Protein Crystallography) bedanken. Hoewel we niet op regelmatige basis samengewerkt hebben is jouw bijdrage aan dit onderzoek van grote waarde geweest. Vooral denk ik dan aan de discussies achter een monitor om de effecten van mutaties te verklaren aan de hand van driedimensionale structuren en natuurlijk aan de scherpe vragen/opmerkingen in de manuscripten. Ook Henriëtte heeft een belangrijke bijdrage aan dit boekje geleverd door de structuren van mutant CGTases te bepalen, hetgeen de kwaliteit van vier hoofdstukken heeft verhoogd. In het begin van mijn promotieonderzoek hebben de discussies met Joost en Bart gezorgd voor een snelle overdracht van de CGTase kennis, waarvoor dank. Verder wil ik Maarten (student) bedanken voor zijn screenings werk (hoofdstuk 7), Gea voor de hulp, uitleg en onderhoud van de DSC apparatuur (hoofdstuk 9), Gert-Jan voor het programmeren van Plato (de pipetteerrobot; hoofdstuk 7) en Robert, Michael, Edwin en Janine voor hun hulp en tips bij het layout werk. Tenslotte is deze periode plezierig geweest door de vele microbiologie collega s, met wie koffie gedronken en geborreld werd. Hans Groningen, januari, 2003
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8 CONTENTS Chapter 1 9 General intorduction: The α-amylase family: transglycosylation and hydrolysis reaction specificity Chapter 2 29 Thermoanaerobacterium thermosulfurigenes cyclodextrin glycosyltransferase: mechanism and kinetics of inhibition by acarbose and cyclodextrins Chapter 3 45 The fully conserved Asp residue in conserved sequence region I of the α-amylase family is crucial for the catalytic site architecture and activity Chapter 4 55 The remote substrate binding subsite -6 in cyclodextrin glycosyltransferase controls the enzyme s transferase activity via an induced-fit mechanism Chapter 5 73 Hydrophobic amino acid residues in the acceptor binding site are main determinants for reaction mechanism and specificity of cyclodextrin glycosyltransferase Chapter 6 89 Mutations converting cyclodextrin glycosyltransferase from a transglycosylase into a starch hydrolase Chapter 7 99 Conversion of cyclodextrin glycosyltransferase into a starch hydrolase by directed evolution: the role of Ala230 in acceptor subsite +1 Chapter A five-residue amino acid insertion converts cyclodextrin glycosyltransferase into a starch hydrolase with a high exo-specificity Chapter Improved thermostability of Bacillus circulans cyclodextrin glycosyltransferase by the introduction of a salt-bridge Summary 143 Samenvatting 151 References 157 Overview of mutant CGTases 179 Abbreviations 182 Publication list 183
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