Application of a second generation dendronized polymer for enzyme immobilization on SiO 2

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1 Diss. ETH No Application of a second generation dendronized polymer for enzyme immobilization on SiO 2 A dissertation submitted to ETH-ZURICH for the degree of Doctor of Science presented by SARA FORNERA M.Sc., ETH Zurich born October 26 th, 1983 citizen of Losone, TI, Switzerland accepted on the recommendation of Prof. Dr. Peter Walde, examiner Prof. Dr. A. Dieter Schlüter, co-examiner Prof. Dr. Markku Kulomaa, co-examiner Zürich 2011

2 Abstract An enzymatic cascade reaction is a series of consecutive enzymatic reactions that are performed without product recovery after each step. Enzymatic cascade reactions currently are of great interest for their applications in the regio- and enantioselective synthesis of molecules under mild reaction conditions and for the quantification of analytes. If the enzymes taking part in the reaction are immobilized on a substrate, the easy separation of the enzymes from the reaction solution along with the possible reuse of the enzymes considerably decrease the costs of the process. In this thesis, a second generation water soluble dendronized polymer (de-pg2) was investigated for its potential use as soft organic layer for the immobilization of enzymes on glass. The linker chosen for binding the enzymes to de-pg2 was the noncovalent biotin/avidin system. The enzymes selected for this work were β- galactosidase (β-gal), glucose oxidase (GOD), and horseradish peroxidase (HRP), because they allow the quantification of lactose via an enzymatic cascade reaction. First, β-gal catalyzes the hydrolysis of lactose into D-glucose and D-galactose. Then D-glucose is oxidized into H 2 O 2 and glucono-δ-lactone by GOD; and eventually the quantification of H 2 O 2 is possible via the oxidation of ortho-phenylenediamine (OPD) by HRP. Initially, the possible advantages of using de-pg2 versus the conventional polymer α-d-polylysine (PDL) for enzyme immobilization on glass were investigated. The reactivity of the amino groups at the periphery of de-pg2 regarding biotinylation was found to be comparable to the reactivity of the ε-amino groups of PDL. The adsorption behaviour of de-pg2 and PDL on SiO 2 was studied with the Transmission Interferometric Adsorption Sensor (TInAS). The adsorption behaviour of de-pg2 was found to be more reproducible as compared to PDL. Moreover, the de-pg2 adsorbed layer was more resistant to acidic desorption than the PDL adsorbed layer. These two observations could be a consequence of the fact that de-pg2 has four amino groups per repeating unit while PDL has only one. This renders the backbone of de-pg2 more rigid and the polymer more positively charged than PDL. These two features V

3 could favour the more stable and neater adsorption on the glass surface in the case of de-pg2 as compared to PDL. In the beginning of the enzyme immobilization, either biotinylated de-pg2 or biotinylated PDL were adsorbed on glass in the TInAS flow cell. Avidin was specifically adsorbed on the layer composed of the biotinylated polymer. Afterwards, biotinylated HRP was adsorbed on the polymer/avidin layer. The TInAS studies showed that de-pg2 clearly immobilized a larger amount of HRP than PDL. Therefore, the adsorption of GOD and β-gal was studied in the TInAS flow cell with de-pg2 as soft organic layer only. The adsorption conditions that minimized the unspecific enzyme adsorption on the de-pg2/avidin layer were optimized. Under appropriate adsorption conditions, the unspecific adsorption of HRP and GOD could be avoided. In case of β-gal, a maximum of 8% unspecific adsorption was reached. Eventually, it was proven, via in situ TInAS activity measurements, that the immobilized enzymes retained their capability of catalyzing one step of the cascade reaction necessary for lactose quantification. In the last part of the project, the cascade reaction involving all three enzymes was analyzed. First, the enzymatic cascade reaction for the one-pot quantification of lactose via β-gal/god/hrp was optimized with all the enzymes dissolved in solution. Then, using the protocol for enzyme immobilization on glass established with the TInAS, the enzymes were immobilized on commercially available glass slides. Also in this case, de-pg2 was found to be better than PDL as soft organic layer. When HRP was immobilized with de-pg2/avidin on glass, HRP retained twice the activity as compared to HRP immobilized with PDL/avidin after four weeks storage in phosphate buffer. Afterwards, the three enzymes were immobilized inside three glass tubes with the help of the de-pg2/avidin layer. When the tubes were connected in the β-gal/god/hrp sequence, lactose could be quantified, using OPD as chromogenic substrate for HRP. As last application of this cascade reaction system, β-gal, GOD, and HRP were immobilized sequentially with the help of de-pg2/avidin inside a microfluidic reactor (glass/polydimethylsiloxane). The quantification of lactose was possible also in this case. The stability of the system during storage was studied and found to be promising for future applications in which the stable immobilization of different types of enzymes is required. VI

4 The presented successful immobilization approach is expected to be generally applicable for any synthetic and analytical reaction in which multiple enzymatic steps are required. Furthermore, preliminary results showed that the formation of the de-pg2/enzyme conjugate via the avidin/biotin system is possible in solution, as demonstrated with HRP as model enzyme. After conjugation with de-pg2 in solution, HRP remained active. VII

5 Riassunto Nei processi di catalisi enzimatica, l immobilizzazione di enzimi su substrati è un aspetto di fondamentale importanza per applicazioni industriali in quanto il recupero e riutilizzo del catalizzatore comporta minori costi d esercizio. A questo scopo, nell ambito di questa tesi di dottorato, è stato studiato l uso del polimero dendronizzato de-pg2 come strato organico per l immobilizzazione di enzimi sul vetro. α-d-polilisina (PDL) è stata utilizzata per un confronto come strato organico di riferimento. Al fine di verificare che il processo d immobilizzazione non influenzi negativamente l attività catalitica dell enzima, la reazione a cascata enzimatica utilizzata per la quantificazione del lattosio è stata presa in considerazione. Gli enzimi coinvolti in questa reazione sono la β-galattosidasi (β-gal), che catalizza l idrolisi del lattosio a D-glucosio e D-galattosio, la glucosio ossidasi (GOD), che catalizza l ossidazione di β-d-glucosio in gluco-δ-lactone e H 2 O 2, e la perossidasi del radicchio (HRP), che nell ultimo step reattivo quantifica la concentrazione di H 2 O 2 prodotta attraverso l ossidazione dell orto-difenildiammina (OPD). In una prima fase del lavoro, sono stati investigati i possibili vantaggi dell utilizzo del polimero dendronizzato de-pg2 rispetto alla PDL come strato organico per immobilizzare gli enzimi sul vetro. Durante il processo di biotinilizzazione la reattività dei gruppi aminici dei due polimeri (de-pg2 e PDL) è risultata simile. L adsorbimento al vetro dei due polimeri è stato monitorato con il sensore d adsorbimento Transmission Interferometric Adsorption Sensor TInAS. L adsorbimento del de-pg2 si è dimostrato più riproducibile di quello della PDL. Inoltre lo strato formato dal de-pg2 è risultato più resistente rispetto al desorbimento dovuto all effetto di soluzioni acide. Entrambi questi risultati potrebbero essere una conseguenza del fatto che l unità ripetitiva del de-pg2 è più voluminosa di quella della PDL e presenta quattro gruppi aminici alla periferia. Ne consegue che la catena del de-pg2 è più rigida di quella della PDL e che il de-pg2 presenta una maggiore carica positiva della PDL. Il protocollo per l immobilizzazione degli enzimi sul vetro prevedeva tre fasi successive d adsorbimento: (i) il polimero biotinilato è stato adsorbito sul vetro, (ii) l avidina è stata adsorbita sullo strato di polimero, e (iii) l enzima biotinilato è stato VIII

6 coniugato all avidina. Al fine di valutare l influenza dello strato organico nel processo d immobilizzazione, HRP è stata immobilizzata sia con de-pg2 che con PDL. Lo studio con il TInAS ha mostrato che de-pg2 è più efficiente nell immobilizzare l HRP rispetto alla PDL. Inoltre, l analisi dell attività enzimatica dell HRP durante lo stoccaggio in soluzione tampone ha rivelato una maggiore stabilità dell HRP quando è stata immobilizzata sul vetro con lo strato de-pg2/vetro. Le condizioni durante l adsorbimento monitorato con il TInAS sono state variate per adsorbite HRP e GOD unicamente in modo specifico. Nel caso della β-gal, è stato misurato un massimo di 8% d adsorbimento non specifico. Mediante misure di attività condotte in situ, è stato dimostrato che tutti e tre gli enzimi immobilizzati conservano l attività catalitica. Nell ultima parte del progetto, la reazione a cascata alla quale prendono parte tutti e tre gli enzimi è stata analizzata. In primo luogo la reazione a cascata enzimatica per la quantificazione del lattosio via β-gal/god/hrp è stata ottimizzata quando tutti e tre gli enzimi erano in soluzione. In seguito il protocollo per l immobilizzazione degli enzimi messo a punto con il TInAS è stato applicato per immobilizzare i diversi enzimi con lo strato de-pg2/avidina all interno di tre differenti tubi di vetro. Come previsto, unicamente collegando i tubi con immobilizzati gli enzimi nella sequenza β- Gal/GOD/HRP la concentrazione del lattosio in soluzione era quantificabile. Gli enzimi β-gal, GOD e HRP sono anche stati immobilizzati in sequenza all interno di un unico microchip (vetro/polidimetilsilossano). Anche in questo caso la quantificazione del lattosio è stata possibile. Questa scoperta apre le porte a nuove possibili applicazioni del sistema presentato nelle quali diversi enzimi vengono immobilizzati in sequenza all interno dello stesso microchip per quantificare diverse sostanze o per sintetizzare una molecola con una reazione a cascata enzimatica. Inoltre, usando HRP come enzima modello, è stato dimostrato che il coniugato de- PG2/enzima può essere formato anche direttamente in soluzione usando il sistema biotina/avidina. Dopo la coniugazione, l enzima è ancora attivo. IX

7 Zusammenfassung Eine Kaskadenreaktion ist eine Reihe aufeinanderfolgender enzymatischer Reaktionen, die ohne Produktrückgewinnung zwischen den einzelnen Schritten durchgeführt wird. Enzymatische Kaskadenreaktionen sind zur Zeit von grossem Interesse aufgrund ihrer Anwendungen in der regio- und enantioselektiven Molekülsynthese unter milden Reaktionsbedingungen und zur Quantifizierung von Analyten. Wenn die an einer Reaktion teilnehmenden Enzyme auf einem Substrat immobilisiert werden, verringert die einfache Trennung der Enzyme von der Reaktionslösung und daraus folgend die mögliche Wiederverwendung der Enzyme die Kosten des Prozesses signifikant. In dieser Arbeit wurde ein wasserlösliches, dendronisiertes Polymer zweiter Generation (de-pg2) auf sein Potential hin untersucht, als weiche organische Schicht zur Enzymimmobilisierung auf Glas genutzt zu werden. Die Enzyme wurden durch das nicht-kovalente Biotin/Avidin-System an de-pg2 gekoppelt. Die Enzyme β- Galaktosidase (β-gal), Glukose-Oxidase (GOD) und Meerrettichperoxidase (HRP) wurden für diese Arbeit ausgewählt, da sie die Quantifizierung von Laktose über eine enzymatische Kaskadenreaktion ermöglichen. Zunächst katalysiert β-gal die Hydrolyse von Laktose zu D-Glukose und D-Galactose. Dann wird D-Glukose durch GOD zu H 2 O 2 und Glucono-1,5-lacton oxidiert; und schliesslich ist die Quantifizierung von H 2 O 2 durch die Oxidation von ortho-phenylendiamin (OPD) durch HRP möglich. Im ersten Teil der Arbeit wurden die möglichen Vorteile der Nutzung von de-pg2 anstelle des konventionellen α-d-polylysin (PDL) zur Enzymimmobilisierung auf Glas untersucht. Die Reaktivität der Aminogruppen an der Peripherie von de-pg2 bezüglich der Biotinylierung ist vergleichbar mit der Reaktivität der ε-aminogruppen von PDL. Das Adsorptionsverhalten von de-pg2 und PDL SiO 2 wurde mit dem Transmission Interferometric Adsorption Sensor (TInAS) untersucht. Das Adsorptionsverhalten von de-pg2 war dabei besser reproduzierbar als jenes von PDL. Ausserdem war die adsorbierte de-pg2-schicht resistenter gegenüber saurer Desorption als die PDL-Schicht. Diese zwei Beobachtungen könnten eine direkte X

8 Folge der Tatsache sein, dass de-pg2 über vier Aminogruppen pro Wiederholungseinheit verfügt und PDL nur über eine. Dies macht den Hauptstrang von de-pg2 steifer und das Polymer wird stärker positiv geladen als PDL. Diese Eigenschaften begünstigen eine stabilere und sauberere Adsorption auf der Glasoberfläche im Fall von de-pg2 verglichen mit PDL. Zu Beginn der Enzymimmobilisierung wurden entweder biotinyliertes de-pg2 oder biotinyliertes PDL in der TInAS-Flusszelle auf Glas adsorbiert. Avidin wurde dann auf der biotinylierten Polymerschicht adsorbiert. Danach wurde biotinyliertes HRP auf der Polymer/Avidin-Schicht adsorbiert. Die TInAS-Messungen zeigten, dass de- PG2 eine deutlich grössere Menge HRP immobilisierte als PDL. Daher wurde die Adsorption von GOD und β-gal in der TInAS-Flusszelle nur mit de-pg2 als weicher organischer Schicht untersucht. Die Adsorptionsbedingungen wurden auf eine minimale unspezifische Enzymadsorption auf der de-pg2/avidin-schicht optimiert. Unter geeigneten Adsorptionsbedingungen konnte die unspezifische Adsorption von HRP und GOD gänzlich vermieden werden. Im Fall von β-gal wurde ein Maximum von 8% unspezifischer Adsorption erreicht. Letztendlich konnte mittels in situ TInAS- Aktivitätsmessungen bewiesen werden, dass die immobilisierten Enzyme ihre Fähigkeit behielten, einen Schritt der Kaskadenreaktion zu katalysieren, der für die Laktosequantifizierung notwendig ist. Im letzten Teil des Projekts wurde die Kaskadenreaktion mit allen drei Enzymen analysiert. Zunächst wurde die enzymatische Kaskadenreaktion für die one pot - Quantifizierung von Laktose mit β-gal/god/hrp optimiert, wobei alle Enzyme gelöst vorlagen. Daraufhin wurden die Enzyme auf kommerziell erhältlichen Glassscheiben immobilisiert, wobei das zuvor erarbeitete Protokoll zur Enzymimmobilisierung auf Glas mit TInAS genutzt wurde. Auch hier stellte sich de- PG2 als weiche, organische Schicht wieder als besser geeignet als PDL heraus. Im Fall von immobilisiertem HRP mit de-pg2/avidin auf Glas, hatte HRP nach vierwöchiger Lagerung in einer Phosphatlösung die doppelte Aktivität verglichen mit jener von HRP auf PDL/Avidin. Danach wurden die drei Enzyme mithilfe der de- PG2/Avidin-Schicht in drei Glasröhrchen immobilisiert. Wenn die Röhrchen in der Sequenz β-gal/god/hrp verknüpft wurden, konnte Laktose unter Nutzung von OPD als chromogenem Substrat für HRP quantifiziert werden. XI

9 Als letzte Anwendung dieses Kaskadenreaktions-Systems wurden β-gal, GOD und HRP nacheinander mithilfe der de-pg2/avidin-schicht in Glas-Polydimethylsiloxan- Mikrokanälen immobilisiert. Die Quantifizierung von Laktose war auch in diesem Fall möglich. Die Stabilität des Systems während Lagerung wurde untersucht und ist vielversprechend für zukünftige Anwendungen, die eine stabile Immobilisierung verschiedener Enzymtypen erfordern. Der vorgestellte, erfolgreiche Ansatz der Immobilisierung ist voraussichtlich auf prinzipiell jede synthetische und analytische Reaktion anwendbar, die mehrere enzymatische Schritte benötigt. Zudem zeigen vorläufige Ergebnisse, dass die Bildung der de-pg2/enzym- Konjugate mit dem Avidin/Biotin-System in Lösung möglich ist, wie mit HRP als Modellenzym gezeigt werden konnte. Nach der Konjugation mit de-pg2 in Lösung bleibt HRP aktiv. XII

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