Mussel-inspired Polymerization

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2 Mussel-inspired Polymerization Justus Horsch and Hans G. Börner* Humboldt-Universität zu Berlin, Department of Chemistry, Brook-Taylor-Str. 2, D Berlin Bio-inspiration is a key feature in the development of advanced materials and is gaining interest in a variety of fields. [1] Biological concepts, mechanisms and design features can be used as a source of guiding principles and ideas for new materials with improved properties. Marine mussels like mytilus edulis are a well investigated example as a source of inspiration for researchers. They overcome the problem of difficult adhesion conditions in salty ocean water by expressing adhesive proteins in their holdfast termed byssus. These proteins contain 3,4-dihydroxyphenylalanine (DOPA), a catecholic amino acid, in amounts of up to 28 mol%. [2] Hence DOPA containing mussel-inspired polymers are of interest for researchers as they form strong adhesives and coatings. For example anti-fouling coatings were studied extensively, where polyethylene oxide (PEO) and other polymers are conjugated with DOPA functionalities or DOPA containing domains. [2-3] Herein we report a new approach of enzymatic induced polymerization to form musselinspired polymers with high DOPA content. Therefor tyrosine and cysteine containing peptide oligomers act as unimers. Upon oxidation of tyrosine to DOPAquinone by the enzyme tyrosinase unimers are being activated and able to polymerize by forming cysteinyl-dopabonds which then present DOPA functionalities to interact with surfaces. Figure 1: Scheme of enzymatic induced polymerization approach. [1] E. Dujardin, S. Mann, Adv. Mater. 2002, 14, [2] B. P. Lee, P. B. Messersmith, J. N. Israelachvili, J. H. Waite, Annu. Rev. Mater. Res. 2011, 41, [3] P. Wilke, H. G. Börner, ACS Macro Letters 2012, 1,

3 MALDI-Imaging of large peptide libraries to rapidly select high affinity binders for pharmaceutical applications Dario Remmler, Hans G. Börner* Department of Chemistry, Laboratory for Organic Synthesis of Functional Systems, Humboldt- Universität zu Berlin, Brook-Taylor-Str. 2, Berlin One-bead-one-compound libraries are powerful tools to select high affinity binders. This combinatorial methodology proved to be valuable for a large variety of applications. However, library design as well as the selection of positive hits and sequencing of peptides on identified beads is tedious and highly challenging. One of the major limitations results from the desired size of the library to increase the probability to identify excellent binders. Although common polymer beads of 500 µm are easy to handle, a high diversity of e.g particles requires ~66 kg of particles. As this approach does not seem practically advisable, the use of customized 10 µm particles is planned. This requires screening of only 0.5 g of particles in respect to the same diversity. Small beads of 10 µm would enable to realize large peptide libraries, but the particle size limits the ease of manipulation, selection and sequencing. Modern MALDI-TOF-TOF MS/MS mass spectrometry imaging combines extreme sensitivity with excellent lateral resolution. Within the project an analytical high-throughput platform will be developed using MALDI-Imaging to screen and identify high affinity binders. Figure 1 shows the experimental setup with peptide-loaded resin beads glued onto a MALDI plate. The project will demonstrate the applicability to realize specific drug transporters [1] by selecting high affinity binders for high potential drugs, where solubility causes currently undesired pharmacological profiles [2]. MALDI-Laser Mass spectrum MALDI-Plate Resin Photolinker Peptide Figure 1. Schematic presentation of the method to identify high affinity binders by MALDI-TOF- TOF MS/MS. [1] Wieczorek, S., et al., Exploiting Specific Interactions toward Next-Generation Polymeric Drug Transporters. Journal of the American Chemical Society, (5): p [2] Kawabata, Y., et al., Formulation design for poorly water-soluble drugs based on biopharmaceutics classification system: Basic approaches and practical applications. International Journal of Pharmaceutics, (1): p

4 A new strategy to switch diarylethenes reliably with visible light in both directions Sebastian Fredrich*, Robert Göstl, Martin Herder, Lutz Grubert, Jutta Schwarz, Stefan Hecht Humboldt-Universität zu Berlin, Department of Chemistry, Brook-Taylor-Str. 2, Berlin Diarylethenes are one of the most promising classes of light-operated molecular switches. [1] Their photochromism typically involves two thermally stable isomers with distinct absorption spectra and tunable electronic properties, resulting from the underlying 6π-electrocyclization. Their high fatigue resistance, the capacity to undergo many switching cycles without considerable degradation, is an often mentioned feature. However, most diarylethenes show significant side product formation upon irradiation with UV-light. [2] In addition, there are several strategies to bathochromically shift the absorption of the ring-open isomer to the visible range, for example via the elongation of the π-system. [3] Here, we show that triplet sensitizers offer a unique way to induce ring-closure using visible light and furthermore inhibit the formation of the photochemical side product, thereby leading to much improved diarylethenes, which can be addressed in both directions using visible light and don t suffer from fatigue. [4] In initial sensitization experiments we explored and established triplet sensitization as a viable route to induce ring-closure of the diarylethene. [5] Subsequently, we covalently linked the sensitizer to the diarylethene skeleton rendering the sensitization event independent of the concentration. Two dithienylethene photoswitches with covalently linked 1,2-diketone tripletsensitizing moieties were synthesized and their spectroscopic properties were investigated. It turned out that the diarylethene derivative with the sensitizer attached via a conjugated linker offers both strongly red-shifted absorption as well as high fatigue resistance, resulting from the extended π-system on the one hand and the efficient population of the triplet excited state. An additional aspect resulting from the photochemistry taking place on the triplet manifold concerns the strong dependence of switching efficiency on the oxygen content due to in situ formation of singlet oxygen, a phenomenon which could potentially be used for further applications of this new type of diarylethene photoswitches. s [1] Reviews are given in: a) M. Irie, T. Fukaminato, K. Matsuda, S. Kobatake, Chem. Rev. 2014, 114, , b) B. L. Feringa, Molecular Switches, Wiley-VCH, Weinheim, c) M. Irie, Y. Yokoyama, T. Seki, New Frontiers in Photochromism, Springer Japan, [2] M. Irie, T. Lifka, K. Uchida, S. Kobatake, Y. Shindo, Chem. Commun. 1999, [3] a) O. Tosic, K. Altenhoner, J. Mattay, Photochem. Photobiol. Sci. 2010, 9, b) G. M. Tsivgoulis, J.-M. Lehn, Chem. Eur. J. 1996, 2, [4] Unpublished. [5] For related work see for example: a) R. T. F. Jukes, V. Adamo, F. Hartl, P. Belser, L. De Cola, Inorg.Chem. 2004, 43, , b) M. Herder, B. Schmidt, L. Grubert, M. Pätzel, J. Schwarz, S. Hecht, J. Am. Chem. Soc. 2015, 137,

5 ortho-fluoroazobenzenes: Visible-Light Switches with Improved Properties Christopher Knie, Fangli Zhao, Stefan Hecht and David Bléger* Humboldt-Universität zu Berlin, Department of Chemistry, Brook-Taylor-Straße 2, D Berlin The control over structure, properties, and eventually function of molecular systems offers great possibilities in material and life sciences. In this sense, employing light as a stimulus is desirable considering its spatiotemporal resolution and the non-invasive application. However, wellestablished photoswitches, e.g. diarylethenes, [1] stilbenes, [2] azobenzenes, [3] or spiropyrans, [4] usually require UV light to trigger the isomerization process in at least one direction. Drawbacks of UV light comprise low penetration and the detrimental character to biological environments. Therefore, derivatives of the afore mentioned photoresponsive molecules are targeted that render isomerization with exclusively visible light possible. Ortho-fluorinated azobenzenes meet this requirement by exhibiting a relative large shift of the nπ*-band upon isomerization enabling the switching process by visible light only. [5] High photoconversions as well as remarkably long thermal half-lifes of the thermodynamically unstable Z-isomers complete their beneficial properties. Differently substituted derivatives of the ortho-fluorinated azobenzene have been prepared and compared according to their spectral properties and isomerization behavior. [6] Electron withdrawing groups, i.e. esters or amides, further increase the splitting of the nπ*-bands resulting in photostationary states that are highly enriched with one isomer ( 90%). [1] M. Irie, Chem. Rev. 2000, 100, [2] D. H. Waldeck, Chem. Rev. 1991, 91, [3] H. M. D. Bandara, S. C. Burdette, Chem. Soc. Rev. 2012, 41, [4] R. Klajn, Chem. Soc. Rev. 2014, 43, [5] D. Bléger, J. Schwarz, A. M. Brouwer, S. Hecht, J. Am. Chem. Soc. 2012, 134, [6] C. Knie, M. Utecht, F, Zhao, H. Kulla, S. Kovalenko, A. M. Brouwer, P. Saalfrank, S. Hecht, D. Bléger, Chem. Eur. J. 2014, 20,

6 Synthese neuartiger frustrierter Lewis-Paare mit Lewis-sauren Bismutzentren auf Basis eines Xanthen-Rückgrats Karolin Materne* and Christian Limberg Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, Berlin Frustrierte Lewis-Paare (frustrated Lewis pairs - FLPs) basieren auf einer Kombination von sterisch anspruchsvollen Lewis-Säuren und Lewis-Basen, welche nicht in der Lage sind eine Neutralisationsreaktion miteinander einzugehen, um klassische Lewis-Addukte zu bilden. Dennoch kann ihre kooperative Acidität/Basizität genutzt werden: so sind FLPs bekannt, welche kleine Moleküle wie H 2 oder CO 2 aktivieren und/oder transformieren können. [1],[2] Es gibt sowohl inter- als auch intramolekulare Systeme, welche häufig auf einer Kombination von Phosphor-Donoren und Bor-Akzeptoren basieren. [1] In diesem Zusammenhang schien es denkbar, dass auch Bismut(III)-Zentren als Lewis-acide Einheiten geeignet sind, und elektronenreiche d 8 -Übergangsmetallfragmente, welche über ein besetztes, Lewis-basisches d z 2-Orbital verfügen, als Lewis-Base. [3] Für ein solches System wählten wir ein Xanthenbasiertes Rückgrat, da der Bi M-Abstand für eine direkte Lewis-Säure/Base-Wechselwirkung zu groß sein dürfte, aber dennoch Wechselwirkungen eines Substrates S erlauben sollte. Ausgehend von XanI 2 erfolgte durch selektive Lithiierung und nachfolgende Umsetzung mit Ph 2BiCl zunächst die Anbindung der entsprechenden Bismut-Einheit am Xanthen-Rückgrat und damit die Darstellung von Xan(BiPh 2)I. Anschließend wird durch Verwendung geeigneter M 0 - Vorläufer (M = Ni, Pd) das Übergangsmetall in die zweite C I-Bindung insertiert. Dabei weist M eine quadratisch planare Koordinationsumgebung auf, wobei das d z 2-Orbital in Richtung des Lewis-sauren Bismutzentrums ausgerichtet ist, so dass ein FLP-artiges Arrangement entsteht, welches sich zur Aktivierung eines Substrates nutzen lassen sollte. Literatur [1] D. W. Stephan, G. Erker, Angew. Chem. Int. Ed. 2010, 49, 46. [2] G. Ménard, T. M. Gilbert, J. A. Hatnean, A. Kraft, I. Krossing, D. W. Stephan, Organometallics 2013, 32, [3] C. Tschersich, C. Limberg, S. Roggan, C. Herwig, N. Ernsting, S. Kovalenko, S. Mebs, Angew. Chem. Int. Ed. 2012, 51, 4989.

7 Synthesis of a Chiral, Polydentate Ligand System setting out from L-Cysteine and investigation of its Nickel complexes Dana S. Warner *, Stefan Mebs, Beatrice Braun, Christian Limberg Humboldt-Universität zu Berlin, Institute for Chemistry, Brook-Taylor-Str. 2, Berlin, Deutschland. Cysteinate is one of the most abundant amino acid ligands found within the active sites of metalloproteins. For example the nickel ions in acetyl coenzyme A synthase (ACS) or in the [NiFe] hydrogenase are exclusively coordinated by cysteinate units. [1] In attempts to prepare structural or functional model compounds for the active center of the ACS, polydentate thiolates have been employed to mimic cysteinate ligand environments. [2,3] In our work, we set out from protected natural L-cysteine to synthesize a 2,5-diketopiperazine. [4] Reduction with NaBH 4/TiCl 4 leads to N,N'-dimethyl-(2R,5R)-bis-(sulfanylmethyl) piperazine, LH 2, the thiol functions of which electronically resemble cysteine. Hence, LH 2 represents a novel, chiral ligand precursor to mimic Ni(Cys) n sites. [5] Deprotonation of LH 2 with NaOMe followed by treatment with NiBr 2(dme) led to the isolation of a diastereomerically pure nickel complex [LNi] 2. In [LNi] 2 each Ni center is coordinated by two thiolate and one amino donor functions, and these entities dimerise to give [LNi] 2. Cyclic voltammetry indicated the possibility of Ni II Ni III oxidation for this complex. [5] [LNi] 2 may be regarded as a structural model for the A cluster within the ACS, which also contains two Ni centers bridged by cysteinate functions, as some of the metric data compare well. By the conversion of [LNi] 2 with nucleophiles like KSEt or KCN, the Ni-(µ 2-S)-Ni bridges are cleaved to afford planar mononuclear products, which represent interesting precursor compounds to set out from for biomimetic or bioinspired studies. [1] C. Darnault, A. Volbeda, E. J. Kim, P. Legrand, X. Vernède, P. a Lindahl, J. C. Fontecilla- Camps, Nat. Struct. Biol. 2003, 10, [2] R.C. Linck, C. W. Spahn, T. B. Rauchfuss, S. R. Wilson, J. Am. Chem. Soc. 2003, [3] R. Krishnan, C.G. Riordan, J. Am. Chem. Soc. 2004, [4] D. Iannotta, N. Castellucci, M. Monari, C. Tomasini, Tetrahedron Lett. 2010, 51, [5] D. Warner, S. Mebs, C. Limberg, Z. Anorg. Allg. Chem. 2013,

8 Recent progress in the application of the method of increments to weakly interacting systems Marcel John, Humboldt-Universität zu Berlin, Institut für Chemie, Berlin, Germany; Joachim Friedrich, Technische Universität Chemnitz, Institut für Chemie, Chemnitz, Germany; Elena Voloshina, Humboldt-Universität zu Berlin, Institut für Chemie, Berlin, Germany; Joachim Sauer, Humboldt-Universität zu Berlin, Institut für Chemie, Berlin Although DFT methods are widely used because they are able to describe quantitatively different systems at low computational cost, they fail in the case of van der Waals interactions. Approximation-based approaches like the dispersion correction [1] tackled this problem, but the lack of systematic improvability of the DFT methods remains. From the point of theory the wavefunction-based methods, especially CCSD(T), are more suitable for studying weakly interacting systems, but their unfavorable scaling with respect to the increasing system size limits their application to moderate-sized systems. This problem can be circumvented by exploiting the fact that electronic correlation is an intrinsically short-ranged phenomenon which leads to the group of the so-called local correlation methods. One of these is the method of increments [2-4] which is a type of manybody expansion of the correlation energy. This method is used to calculate the energies of clusters and periodic systems on the MP2 and CCSD(T) level of theory. Therefore different approaches of the incremental scheme were implemented as a automatized program to compare accuracy, efficiency and hardware requirements among each other and to the calculation of the entire system. [1] S. Grimme, J. Antony, S. Ehrlich, H. Krieg, The Journal of Chemical Physics 2010, 132, [2] H. Stoll, Phys. Rev. B 1992, 46, [3] J. Friedrich, J. Chem. Theory Comput. 2012, 8, [4] E. Voloshina, D. Usvyat, M. Schütz, Y. Dedkov, B. Paulus, Phys. Chem. Chem. Phys. 2011, 13,

9 The Influence of Water on the Oxidation of Methanol at the Ceria (111) Surface Thomas Kropp,* Joachim Paier, and Joachim Sauer Humboldt-Universität zu Berlin, Unter den Linden 6, D Berlin The oxidative dehydrogenation (ODH) of methanol has become an important model reaction to study C H bond activation (see ref 1 and references therein), and the reducible cerium oxide proves to be an active catalyst for this reaction due to its low oxygen defect formation energy. 2 The ODH of methanol to formaldehyde at the thermodynamically most stable ceria (111) surface has been frequently studied (see, e.g., refs 3 and 4), and recently accurate energy barriers have been calculated for this reaction, 5 which proceeds according to a Mars van Krevelen mechanism involving the following elementary steps: the dissociative adsorption of methanol, the rate-determining hydrogen transfer, the desorption of water and formaldehyde, and a fast reoxidation step. Surface oxygen vacancies were found to be the preferred active sites with an intrinsic barrier of 139 kj/mol (HSE+D). 5 This theoretical value agrees well with the experimental results obtained by Freund and coworkers via temperature-programmed desorption experiments. 6 Water adsorption at the ceria (111) surface has also been abundantly studied (see, e.g., refs 7 and 8), but the effect of water on the ODH of methanol has yet to be addressed. Studying the co-adsorption of water and methanol represents the next step in understanding the methanol oxidation under realistic conditions. s [1] Ganduglia-Pirovano, M. V.; Popa, C.; Sauer, J.; Abbott, H. L.; Uhl, A.; Baron, M.; Stacchiola, D.; Bondarchuk, O.; Shaikhutdinov, S.; Freund, H.-J. J. Am. Chem. Soc. 2010, 132, [2] Gorte, R. AlChE J. 2010, 56, [3] Ferrizz, R. M.; Wong, G. S.; Egami, T.; Vohs, J. M. Langmuir 2001, 17, [4] Albrecht, P. M.; Mullins, D. R. Langmuir 2013, 29, [5] Kropp, T.; Paier, J. J. Phys. Chem. C 2014, 118, [6] Abbott, H. L.; Uhl, A.; Baron, M.; Lei, Y.; Meyer, R. J.; Stacchiola, D. J.; Bondarchuk, O.; Shaikhutdinov, S.; Freund, H. J. J. Catal. 2010, 272, 82. [7] Henderson, M. A.; Perkins, C. L.; Engelhard, M. H.; Thevuthasan, S.; Peden, C. H. F. Surf. Sci. 2003, 526, 1. [8] Fernández-Torre, D.; Kosmider, K.; Carrasco, J.; Ganduglia-Pirovano, M. V.; Pérez, R. J. Phys. Chem. C 2012, 116,

10 Expanding the Transfer-Chemistry Toolbox: Comparison between Thioester- and Sulfonate-based Templated Reactions Katharina Gröger, Prof. Oliver Seitz 1 1 Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor-Str. 2, D Berlin The interaction between peptides and cognate proteins has been used to trigger chemical reactions which may lead to ligation of two peptide fragments or to attachment of a reporter group to a protein of interest. Since the introduction of native chemical ligation in 1994, [1] it became one of the most established methods for the ligation of peptides and was further applied in templated reactions between peptides or oligonucleotides. [2,3] Another reaction which draws on the attack of a nucleophilic amino acid moiety is the ligand directed tosylate chemistry introduced by Hamachi et al. [4] This chemistry proved to be useful for oligonucleotide-based templated chemistry as well as protein-labelling. [5] Both, thioesters and sulfonates are attractive tools for conjugation chemistry in live cell environments. Here we compare thioester- with sulfonate-based chemistry in peptide-templated protein-pna conjugation reactions. Coiled-coil peptide pairs serve as guiding units that trigger highly target-specific proximity driven reactions between a donating PNA-peptide conjugate and an accepting peptide / protein. For the synthesis of the reactive thioesterlinked or sulfonate-linked PNA-peptide donor conjugates we employed azide-alkyne cycloadditions. Thioester-based PNA transfer reactions proceeded at higher rates than the sulfonate chemistry. Furthermore, the native chemical ligation-type chemistry was amenable to reactivity adjustments simply by varying the mercaptane leaving group (e.g. aliphatic versus aromatic thioesters). By contrast, reactivity tuning proved challenging in case the sulfonate chemistry was used. Drawbacks and advantages are discussed. s [1] Dawson, P.E., Muir, T., Clark-Lewis, I., Kent, S.B., Science 1994, 266, [2] Lee, D.H., Granja, J.R., Martinez, J.A., Severin, K., Ghadiri, M.R., Nature 1996, 382, [3] Grossmann, T.N., Seitz, O., J. Am. Chem. Soc. 2006, 128, [4] Tsukiji, A., Wang, H., Miyagawa, M., Tamura, T., Takaoka, Y., Hamachi, I., J. Am. Chem. Soc. 2009, 131, [5] Kleinbaum, D.J., Kool, E.T., Chem. Commun. 2010, 46,

11 Total Chemical Synthesis and Functional Characterization of Phosphorylated SH3 Protein Domains Robert Zitterbart and Oliver Seitz Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, Berlin Immobilization of receptors on array plates is highly desired, mainly to accomplish an evaluation of a huge variety of potential binders in a fast and parallel fashion. Till now, convenient and rapid methods are only available by immobilization of the ligands. In contrast the immobilization of a variety of proteins and protein-domains in parallel enables a completely new combinatorial paradigm. Herein we present a methodology, which accomplishes this long sought goal by using chemical total synthesis of protein domains to investigate the phosphoregulation of proteins. Phosphorylation is nature s way to regulate protein interactions. We wanted to get a new insight in this mechanism by using our new method as a proof of concept. The method relies on a) self-purifying solid-phase synthesis of peptide thioesters [1] and peptide hydrazides, b) hydrazone ligation for immobilization of cysteinyl-like peptides, c) native chemical ligation and concomitant hydrazone reduction to a stable peptide hydrazide linkage, d) radical-induced desulfurization [2] to afford proteins of native sequence and e) a surfacebased binding assay for functional characterization. The method was used to investigate the phosphoregulation of SH3 domains of man and yeast. We show that the tyrosine phosphorylation can induce both loss and, perhaps surprisingly, gain of ligand affinity of Abl and Arg SH3 domains. This challenges current believes in literature. [1] Mende, F., Beisswenger, M., Seitz, O., J. Am. Chem. Soc. 2010, 132, [2] Haase, C., Rohde, H. Seitz, O., Angew. Chem. Int. Ed. 2008, 47,

12 Controlling monomer sequence; synthesis of complex polymers using supramolecular interactions Meral Yalcin *, Falk Kubatzki* and Niels ten Brummelhuis Humboldt-Universität zu Berlin, Department of Chemistry, Brook-Taloyr-Str.2, D Berlin Nature provides innumerable examples of highly functional structures based on biopolymers such as protein, nucleic acids or carbohydrates. The complex monomer sequences of these polymers are linked to their function through hierarchical folding and self-assembly. A similar control over the monomer sequence in chain-growth polymerization would lead to further control of the polymer properties. [1] In our work we show different approaches to directly influence the monomer sequence in freeradical polymerization. Directional supramolecular interaction, i.e. hydrogen bonding, are used to bring the polymerizable units of monomers in close proximity to each other. Upon polymerization, these monomers are incorporated subsequently in one polymer chain. Furthermore, we investigate alternating cyclocopolymerization of bifunctional monomers and the polymerization of electron-rich and -deficient monomers. The motivation for our work is to create new approaches to synthesize polymers in which monomer sequences are incorporated in a well-defined order. This might proof beneficial for applications in the fields of catalysis or materials chemistry. [2] [1] N. Badi, J.-F. Lutz, Chem. Soc. Rev. 2009, 38, [2] F.H. Schacher, P.A. Rupar, I. Manners, Angew. Chem. Int. Ed. 2012, 51,

13 Entwicklung von Aufgaben zur Förderung von Kompetenzen naturwissenschaftlicher Erkenntnisgewinnung Ines Sonnenschein, Rüdiger Tiemann Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor-Straße 2, D Berlin Laborpraktika sind ein bedeutender Teil der naturwissenschaftlichen Ausbildung an deutschen Hochschulen. Jedoch tragen die Praktika in der Bachelorausbildung wenig zur Entwicklung kritischen Denkens und naturwissenschaftlicher Problemlösestrategien bei (vgl. Hofstein & Kind, 2012). Um Kompetenzen naturwissenschaftlich-experimenteller Erkenntnisgewinnung zu fördern, ist eine wirkungsvolle Unterstützung des Lernprozesses notwendig (Kirschner, Sweller, & Clark, 2006). Das Ziel dieses Teilprojekts ist es daher, Aufgaben, die einen Zugewinn fachlichen und strategischen Wissens ermöglichen, und auf diese Aufgaben abgestimmte instruktionale Unterstützungsmaßnahmen (sog. Prompts), zu entwickeln. Vermittelt über das Prompting soll der Wissenserwerb im Bereich experimenteller Erkenntnisgewinnung gefördert werden. Diese instruktionalen Maßnahmen zeigen sich insbesondere bei Lernenden mit hohem Vorwissen als wirkungsvoll (Künsting, Kempf, & Wirth, 2013), da man davon ausgeht, dass Studierende bereits das Wissen über experimentelle Erkenntnisgewinnungsstrategien besitzen, dies aber in realen Problemsituationen nicht oder nur unzureichend anwenden können (Bannert, 2007). Für die Studie wurden aus dem Fachbereich Analytik Experimentieraufgaben entwickelt, die die Erkenntnisgewinnungsphasen Fragestellung, Hypothese und Planung, Durchführung, und Analyse und Interpretation fokussieren. Abb. 1. Darstellung der Bearbeitung einer Experimentieraufgabe mit drei Aufgabenblocks und dazugehörenden Promptingphasen Die Entwicklung der Aufgaben erfolgte dabei nach inhaltlichen, technischen und formalen Kriterien, die basierend auf den curricularen Vorgaben sowie der aktuellen Literatur zu Prozessen naturwissenschaftlicher Erkenntnisgewinnung, zu Lerntheorie und Lernpsychologie entwickelt wurden. Das Poster stellt den Prozess der Aufgabenentwicklung und testung dar und behandelt im Besonderen die Maßnahmen der Prüfung der Qualität von Realexperimentieraufgaben. Referenzen Bannert, M. (2007). Metakognition beim Lernen mit Hypermedien. Münster, München [u.a.]: Waxmann. Hofstein, A., & Kind, P. M. (2012). Learning in and from science laboratories. In Second International Handbook of Science Education (pp ). Dordrecht: Springer. Kirschner, P. A., Sweller, J., & Clark, R. E. (2006). Why Minimal Guidance During Instruction Does Not Work: An Analysis of the Failure of Constructivist, Discovery, Problem-Based, Experiential, and Inquiry-Based Teaching. Educational Psychologist, 41(2), Künsting, J., Kempf, J., & Wirth, J. (2013). Enhancing scientific discovery learning through metacognitive support. Contemporary Educational Psychology, 38(4),

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