Graduate School of Chemistry and Biochemistry. 5 th April 2005

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1 Universität Bielefeld Graduate School of Chemistry and Biochemistry 7 th Workshop University of Bielefeld aculty of Chemistry 5 th April 2005 Programme The workshop will begin on Tuesday, April 5 th at 09:00 h. All lectures will take place in lecture hall H2. The evening dinner will be at Internationales Begegnungszentrum (IBZ). University of Bielefeld: Directions: Organization: Prof. Dr. Thomas Koop, University of Bielefeld, aculty of Chemistry, Universitätsstr. 25, D Bielefeld Tel.: We look forward to meeting you. inancial support by the Westfälisch-Lippische Universitätsgesellschaft is gratefully acknowledged.

2 Directions: Campus Map: IBZ Lecture Hall H2 Tram Station

3 7 th Workshop Lectures Session I 09:00 09:05 Prof. Dr. Thomas Koop Welcome and Opening Remarks Chairperson: Thomas Koop 09:05 10:00 Prof. Dr. Rolf W. Saalfrank riedrich-alexander-universität Erlangen-ürnberg Metalla-topomers of supramolecular host-guest compounds Main Lecture M1 10:00 10:20 Soumyajit Roy, AC I L2 Giant polyoxomolybdates: Syntheses, structure and stability studies 10:20 10:40 Janine eldmann, PC I L3 Charakterisierung von durch CVD hergestellten Zn x Co 3-x O 4 -Schichten 10:40 11:10 Coffee Break Session II Chairperson: Soumyajit Roy 11:10 11:30 ina Stemmer, BC II und Universität Hamburg L4 Amyloid precursor protein processing and binding partners 11:30 11:50 Imme Domke, AC II L5 Electrochemical Investigations of Various Diazaborole Systems 11:50 12:10 Stefan Eißler, OC III L6 Synthese von epi-d-ent-cryptophycin-52 12:10 12:30 Sonja Krahn, DC I L7 Untersuchung zum intuitiven naturwissenschaftlichen Wissen 2-6Jähriger 12:30 12:50 Daniel oveski, AC III L8 C--Aktivierung und Derivatisierung fluorierter Olefine und Pyridine am Rhodium 12:50 14:15 Lunch Break

4 7 th Workshop Lectures Session III 14:15 15:10 Dr. Rolf Postina Johannes Gutenberg-Universität Mainz Chairperson: Simon Mügge Main Lecture M9 The α-secretase ADAM10, a promising target in the treatment of Alzheimer disease: Identification and functional characterization 15:10 15:30 Henning Sielemann, AC III L10 Methyl- or Ethyl- makes the difference: Solid-state structures of 9,10-Dialkyl-9,10-dihydro-9,10-digallaanthracens 15:30 15:50 Thomas Haase, PC I L11 Investigations in Chemical Vapor Deposition Systems of Silver 15:50 16:10 Philipp Bayer, AC II L12 Invers-polarisierte Arsaalkene als Quelle hochreaktiver Arsinidene 16:10 16:40 Coffee Break Session IV 16:40 17:35 Doz. Dr. Régis Réau CRS-Université de Rennes Chairperson: Patrice okou Main Lecture M13 Organophosphorus π-conjugated systems: rom model molecules to functional materials 17:35 17:55 Sven Weigelt, OC III L14 Synthesis of Efrapeptin Analogues for Conformational Studies 17:55 18:15 Jens Krümberg, AC II L15 Kupferkomplexe von invers polarisierten Phosphaalkenen 18:45 Dinner at Internationales Begegnungszentrum (IBZ)

5 Metalla-topomers of supramolecular host-guest compounds R. W. Saalfrank, I. Bernt, B. Demleitner, H. Glaser, S. Kareth, J. Köhler, V. Seitz and E. Uller Institut für Organische Chemie der Universität Erlangen ürnberg, Henkestraße 42, D Erlangen; AX: M1 The impact of the discovery of crown ethers (mono-, bi-, tricyclic) on the development of different disciplines in chemistry is manifold. Main feature of some of these compounds is that they show properties of biomolecules. We developed a general method for the synthesis of the corresponding metalla-topomers 1-6, using programmed precursors. [1] The products are formed via spontaneous self assembly in a one pot reaction in high yield. Preliminary results of the electronic and magnetic properties of 1-6 are presented. [1] R. W. Saalfrank, A. Stark, K. Peters, H. G. von Schnering, Angew. Chem. Int. Ed. Engl. 1988, 27, 851; R. W. Saalfrank, A. Stark, M. Bremer, H.-U. Hummel, Angew. Chem. Int. Ed. Engl. 1990, 29, 311; R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, Angew. Chem. Int. Ed. Engl. 1994, 33, 1621; R. W. Saalfrank, R. Burak, S. Reihs,. Löw,. Hampel, H.-D. Stachel, J. Lentmaier, K. Peters, E.-M. Peters, H. G. von Schnering, Angew. Chem. Int. Ed. Engl. 1995, 34, or recent reviews see: S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853; J. L. Atwood, L. R. MacGillivray, Angew. Chem. Int. Ed. Engl. 1999, 38, 1018; D. L. Caulder, K.. Raymond, J. Chem. Soc. Dalton Trans, 1999, 1185; Ligand and Metal Control of Self-Assembly in Supramolecular Chemistry, R. W. Saalfrank, B. Demleitner, in Perspectives in Supramolecular Chemistry, Vol. 5 Transition Metals in Supramolecular Chemistry (Ed.: J. P. Sauvage), Wiley-VCH, Weinheim, 1999, pp. 1; Synergistic Effect of Serendipity and Rational Design in Supramolecular Chemistry, E. Uller, B. Demleitner, I. Bernt, R. W. Saalfrank, in Structure and Bonding Vol. 96 (Ed.: M. ujita), Springer, Berlin, 2000, pp. 149.

6 Giant polyoxomolybdates: Syntheses, structure and stability studies L2 Achim Müller*, Soumyajit Roy, Hartmut Bögge, Alice Merca and Marc Schmidtmann Department of Inorganic Chemistry I, University of Bielefeld, D-33615, Bielefeld, Germany. * In this presentation the story of investigation of one of the existing ring-shaped polyoxomolybdates [1] that led to the formation of extended structures [2] and alluded to their potential host-functionalities [3] will be discussed. The structure of water inside the related spherical capsules; [4] the stability of some selected spherical polyoxomolybdates in aqueous solution together with the sites vulnerable to 'attack' by degrading agents and hence responsible for their decomposition will be further proposed (see also igure 1). The presentation will conclude with a perspective for some open questions regarding the generation of these giant polyoxomolybdates from an ionic soup. [5] igure 1. An O 372 framework of an [Mo 132 ] cluster type. The [Mo 132 ] type spherical clusters' decomposition is detected by the change in their Raman spectra induced by the change of the normal coordinates of O 372 framework shown here. [1] A. Müller, S. Roy, Coord. Chem. Rev., 2003, 245, 153. [2] A. Müller, S. Roy, M. Schmidtmann, H. Bögge, Chem. Commun., 2002, [3] a) A. Müller, E. Krickemeyer, H. Bögge, M. Schmidtmann, S. Roy, A. Berkle, Angew. Chem. Int. Ed. 2002, 41, 3604; b) A. Müller, S. K. Das, S. Talismanov, S. Roy, E. Beckmann, H. Bögge, M. Schmidtmann, A. Merca, A. Berkle, L. Allouche, Y. Zhou and L. Zhang, Angew. Chem. Int. Ed. 2003, 42, [4] A. Müller, H. Bögge, E. Diemann, Inorg. Chem. Commun., 2003, 6, 52. [5] A. Müller, S. Roy, Angew. Chem. Int. Ed. (Review to be submitted).

7 Charakterisierung von durch CVD hergestellten Zn x Co 3-x O 4 -Schichten Janine eldmann, aoufal Bahlawane, Katharina Kohse-Höinghaus Universität Bielefeld, Universitätsstr. 25, Bielefeld, Deutschland L3 Mischoxide sind für den Einsatz als katalytische Materialien bei der Totaloxidation von Kohlenwasserstoffen von besonderem Interesse. Sie eignen sich potenziell zum Ersatz üblicher Edelmetallkatalysatoren, weshalb Mischoxidschichten, speziell mit Spinellstruktur, schon eingehend untersucht wurden. Über die katalytische Wirksamkeit von mittels CVD abgeschiedenen Co 3 O 4 -Schichten wurde bereits berichtet [1]. Aus der Literatur [2] geht hervor, dass die katalytische Wirksamkeit von Co 3 O 4 -Schichten bei Pulverbeschichtungen durch die Dotierung mit Zink zu ZnCo 2 O 4 erhöht werden konnte. Deshalb wurden nun dünne Zn x Co 3-x O 4 -ilme aus Co(acac) 2 und Zn(acac) 2 abgeschieden, um den Einfluss von Zink im Gitter besser zu verstehen. Zunächst wurden die Abscheidungsparameter kontrolliert variiert und die abgeschiedenen ilme anhand von XRD, EDX und Raman-Spektroskopie charakterisiert. Dabei zeigte sich, dass Precursortemperatur, Druck und Verweilzeit in diesem CVD-Prozess entscheidend sind, während die Abscheidungstemperatur keinen Einfluss auf die ilmzusammensetzung und die ilmstruktur hatte. Der Anteil an eingelagertem Zink konnte bis zu einem Wert von x = 2 variiert werden, ohne die Spinellstruktur zu verlieren. Auch die Mikrospannung und die Kristallitgröße wurden hierbei nicht signifikant verändert. Die Redox-Eigenschaften der abgeschiedenen ilme wurden mit Hilfe von H 2 -TPR (temperature programmed reduction), und die katalytische Aktivität der Schichten anhand einer katalysierten Verbrennung von Propan untersucht. [1]. Bahlawane, E. ischer Rivera, K. Kohse-Höinghaus, A. Brechling, U. Kleineberg, Appl. Catal. B: Environmental, 53 (2004), [2] G. I. Golodets, Heterogenous Catalytic Reactions Involving Molecular Oxygen, Elsevier Verlag, Amsterdam- Oxford-ew York (1983), S. 441ff.

8 Amyloid precursor protein processing and binding partners ina Stemmer Universität Hamburg, Zentrum für Molekulare eurobiologie, Institut für Biosynthese neuraler Strukturen, alkenried 94, Hamburg L4 Alzheimer s Disease (AD) is a neurodegenerative disorder characterized by the progressive and irreversible loss of neurons. Amyloid precursor protein (APP) is a type I transmembrane protein, which is cleaved by secretases. One of these secretase pathways leads to Ab production and can therefore cause plaque formation, one hallmark of AD. To inhibit this special cleavage, that leads to increased Ab amounts, it is necessary to identifiy molecules binding to the cleavage sites. ollowing the theory of complementary hydropathy we try to find possible new binding partners to the gamma-cleavage site of APP, evaluate the interaction by binding assays and characterize the binding.

9 Electrochemical Investigations of Various Diazaborole Systems Imme Domke Inorganic Chemistry II, University of Bielefeld L5 The reactivity of 1,3,2-diazaboroles towards a broad range of nucleophiles is investigated carefully and described detailed in the literature. [1] Equally the behaviour of these compounds with chemical reductiants was of interest to achieve an diazaborolide anion, which has never been observed as yet. [1] ow, the electrochemistry of 1,3,2-diazaboroles and the corresponding saturated diazaborolidines has been investigated to shed some light into the redox behaviour of such heterocycles. In addition to that, a number of diborole systems are synthesized. B e B B B This spacer molecules are studied electrochemically to get some impression on the communication between the two diazaborole-units. [1] Review: l: Weber, Coord. Chem. Rev. 2001, 215,

10 ovel routes towards the synthesis of cryptophycin analogs S. Eißler, A. Stoncius, C. A. Mast,. Sewald University of Bielefeld, Department of Chemistry; Universitaetsstr. 25, Bielefeld, Germany L6 The cryptophycins (isolated from cyanobacteria ostoc sp.) form a group of tumour-selective cytotoxic cyclic depsipeptides. The enormous activity of cryptophycin 1 against a series of multidrug resistant tumors [1] raised the significant interest in the synthesis of cryptophycins and their analogs over the past decade [2]. We have applied a new convergent synthetic approach towards the total synthesis of cryptophycin analogs. The chirality elements of epoxide fragment A were introduced relying on a single enantioselective catalytic reaction. The other chiral centres are created in a substrate controlled diastereoselective manner [3]. In my work I synthesised the enatiomer of unit A using the unit A synthesis developed by A. Stoncius and C. A. Mast and used it for the synthesis of epi-d-ent-cryptophycin-52: unit D O O O O O unit A unit C H H O O unit B Cl OMe [1] a) Shih C., Teicher B. A., Curr. Pharm. Des., 2001, 7, , b) Wagner M. M., Paul D. C., Shih C., Jordan M. A., Wilson L., Williams D. C., Cancer Chemother. Pharmacol., 1999, 43, [2] Tius M. A., Tetrahedron, 2002, 58, [3] Stoncius A., Mast C. A., Sewald., Tetrahedron: Asymmetry, 2000, 11,

11 Untersuchung zum intuitiven naturwissenschaftlichen Wissen 2-6Jähriger Sonja Krahn, Gisela Lück Universität Bielefeld, akultät für Chemie - Didaktik der Chemie I Postfach , Bielefeld L7 Kinder im Alter von 5-6 Jahren zeigen laut bisheriger Untersuchungen ein großes Interesse an Versuchen zur Physik/Chemie ihre hohe Erinnerungsfähigkeit an die Experimente und deren Deutung zeigt, dass die theoretischen Hintergründe auf einfachem iveau erfasst werden (Lück 2000). Unbestritten ist auch, dass schon sehr junge Kinder (im Alter von wenigen Monaten) über intuitives Wissen zu physikalischen Vorgängen und Eigenschaften verfügen (vgl. Spelke 1992). Studien zur intuitiven Psychologie und Biologie wurden in den letzten 20 Jahren überwiegend mit Kindern ab dem Vorschulalter durchgeführt (z. B. Inagaki & Hatano 1996). Dagegen liegen bislang kaum Untersuchungen zu Wissen über chemische Phänomene, insbesondere dieser Altersgruppe vor. Es gibt zwar Untersuchungen zum Verständnis von Zustandsänderungen und Lösungen (z. B. Osborne & Cosgrove 1983, Slone & Bockhurst 1992), aber diese und andere Untersuchungen berücksichtigen im Wesentlichen erst Kinder ab 5 Jahren. Da bei älteren Kindern die formale Instruktion eine Quelle für die Ausprägung von so genannten misconceptions sein kann, haben wir Untersuchungen mit jüngeren Kindern durchgeführt, um Erfahrungen zu den Anfängen des intuitiven Wissens über chemische Phänomenen zu sammeln. Dazu wurde eine Studie auf der Basis problemzentrierter Interviews mit über 100 Kindern im Alter von 2-7 Jahren durchgeführt. Auch entwicklungsverzögerte Kinder wurden mit einbezogen. Es wurde evaluiert ob und ab welchem Alter Kinder in der Lage sind, warmes von kaltem Wasser durch bloße Wahrnehmung der Wasserdampfbildung zu unterscheiden. Zusätzlich wurde die Einschätzung verschiedener Materialien hinsichtlich ihrer Saugfähigkeit untersucht. Im Vortrag soll die Studie von ihren Anfängen bis zu den Ergebnissen vorgestellt, Perspektiven für weitere Arbeiten aufgezeigt und Konsequenzen für die chemiedidaktische Praxis dargestellt werden. Inagaki, K.; Hatano, G. (1996): Young childrens Recognition of commonalities between animals and plants. In: Child development 67, pp Lück, G. (2000): aturwissenschaften im frühen Kindesalter Untersuchung zur Primärbegegnung von Kindern im Vorschulalter mit Phänomenen der unbelebten atur. aturwissenschaften und Technik Didaktik im Gespräch (33), LIT Verlag, Münster Slone, M.; Bockhurst,.D. (1992): Children s understanding of sugar water solutions. In: International journal of science education 14 (2), pp Spelke, E. S.; Breinlinger, K.; Macomber, J.; Jacobson, K. (1992): Origins of knowledge. In: Psychological Review 99 (4), pp Osborne, R. J. and Cosgrove, M.M (1983): Children s concepts of the changes of state of water. In: Journal of research in science teaching 20 (9), pp

12 C--Aktivierung und Derivatisierung fluorierter Olefine und Pyridine am Rhodium Thomas Braun, Daniel oveski Universität Bielefeld L8 Eine interessante Möglichkeit zur Derivatisierung perfluorierter Verbindungen besteht in deren C-- Aktivierung und einer anschließenden unktionalisierung der gebildeten fluorierten Liganden in der Koordinationssphäre eines Übergangsmetalls. [1,2] Wir konnten zeigen, dass sich Hexafluorpropen und Pentafluorpyridin mit Hilfe von Rhodiumhydrido-Komplexen aktivieren lassen. [3,4] Die Reaktivität der erhaltenen Verbindungen [Rh{C=C(C 3 )}(PEt 3 ) 3 ] und [Rh(4-C 5 4 )(PEt 3 ) 3 ] wird maßgeblich durch den fluorierten anionischen Liganden bestimmt. So reagiert der erhaltene Pyridyl-Komplex [Rh(4-C 5 4 )(PEt 3 ) 3 ] u. a. mit CO und anschließend mit MeI zu einer außergewöhnlich stabilen Acyl-Verbindung, welche sich mit weiterem CO zu einem bisher nicht zugänglichen Keton umsetzen lässt (s. Schema). [3,4] Die Umsetzung des Propen-Derivates [Rh{C=C(C 3 )}(PEt 3 ) 3 ] mit H 2 führt über einen Dihydrido-Komplex als Zwischenstufe zur Bildung von 1,1,1-Trifluorpropan und der Rhodiumfluoro-Verbindung [Rh(PEt 3 ) 3 ] (s. Schema). [3,5] H 3 C O Et 3 P Rh PEt 3 PEt 3 a) CO, -PEt 3 b) CH 3 I Et 3 P Rh PEt 3 H 3 C O I T, CO + [RhI(CO)(PEt 3 ) 2 ] Et 3 P C 3 Rh PEt 3 PEt 3 H 2 Et 3 P H Rh H C 3 PEt 3 PEt 3 2 H2 - H CH 3 CH 2 C 3 + [Rh(PEt 3 ) 3 ] [1] M. I. Sladek, T. Braun, B. eumann, H.-G. Stammler, J. Chem. Soc., Dalton Trans. 2002, 297. [2] T. Braun, R.. Perutz, Chem. Commun. 2002, [3] T. Braun, D. oveski, B. eumann, H.-G. Stammler, Angew. Chem. 2002, 15, 2870; D. oveski, T. Braun, M. Schulte, B. eumann, H.-G. Stammler, Dalton Trans. 2003, [4] D. oveski, T. Braun, B. eumann, A. Stammler, H.-G. Stammler, Dalton Trans. 2004, [5] D. oveski, T. Braun, S. Krückemeier, J. luorine Chem., 2004, 125, 959.

13 The α-secretase ADAM10, a promissing target in the treatment of Alzheimer disease: Identification and functional characterization Rolf Postina Institut für Biochemie, Johannes Gutenberg-Universität Mainz M9 Aβ peptides (Aβ) play an early and central role in Alzheimer disease (AD), the most prevalent neurodegenerative disorder. These peptides are generated in the so-called amyloidogenic pathway by sequencial proteolysis of the amyloid precursor protein (APP), an ubiquitous cell surface type I membrane protein, by β- and γ-secretases. However, the vast majority of APP is constitutively processed within the competing non-amyloidogenic pathway by α- and γ-secretase activities. Here, the α-secretase releases a soluble -terminal APP fragment (APPsα) into the extracellular matrix, which has neurotrophic and neuroprotective properties. In addition, as the α-secretase precludes formation of pathogenic Aβ peptides, this enzymatic activity may represent a protective factor against AD. The molecular origin of the α-secretase activity was elucidated by a biochemical approach (Lammich et al., 1999). Purified ADAM10 (A Disintegrin And Metalloproteinase) was identified to cleave APP-derived peptides at the main α-secretase cleavage site between position 16 and 17 of the Aβ region. urthermore, we demonstrated that ADAM10 possesses α-secretase activity in cultured cells. During our cellular studies on ADAM10 we showed that ADAM10 is synthesized as a catalytically inactive zymogen, and that the proprotein convertases PC7 and furin act as ADAM10 activators by proteolytically removing of the inhibiting ADAM10 prodomain. Moreover, we demonstrated that the ADAM10 prodomain is of essential importance for functional expression of catalytically active ADAM10 (Anders et al., 2001). To prove whether ADAM10 possesses α-secretase activity in vivo, we generated and investigated transgenic mice overexpressing either ADAM10 or the catalytically inactive ADAM10 mutant E384A. Even a moderate neuronal overexpression of ADAM10 in mice transgenic for human APP[V717I] increased the production of secreted neurotrophic APPsα, reduced the formation of Aβ peptides and prevented their deposition in plaques. unctionally, impaired long-term potentiation and cognitive deficits were alleviated. Expression of mutant catalytically inactive ADAM10 led to an enhancement of the number and size of amyloid plaques in the brains of double-transgenic mice. Our results provided the first in vivo evidence for a proteinase of the ADAM family as an α-secretase of APP, thus supporting the hypothesis that a decrease in α-secretase activity contributes to the development of AD (Postina et al., 2004). Our current studies aim to identify cellular pathways leading to an induction of ADAM10 expression and activity. Anders A., Gilbert S., Garten W., Postina R. & ahrenholz. (2001) Regulation of the α-secretase ADAM10 by its prodomain and proprotein convertases. ASEB J. 15: Lammich S., Kojro E., Postina R., Gilbert S., Pfeiffer R., Jasionowski M., Haass C. & ahrenholz. (1999) Constitutive and regulated α-secretase cleavage of Alzheimer s amyloid precursor protein by a disintegrin metalloprotease. Proc. atl. Acad. Sci. USA 96: Postina R., Schroeder A., Dewachter I., Bohl J., Schmitt U., Kojro E., Prinzen C., Endres K., Hiemke C., Blessing M., lamez P., Dequenne A., Godaux E., van Leuven. & ahrenholz. (2004) A disintegrin-metalloproteinase prevents amyloid plaque formation and hippocampal defects in an Alzheimer disease mouse model. J. Clin. Invest. 113:

14 Methyl- or Ethyl- makes the difference: Solid-state structures of 9,10-Dialkyl-9,10-dihydro-9,10-digallaanthracenss Henning Sielemann Inorganic Chmeistry III, University of Bielefeld L10 The donor-free 9,10-dialkyl-9,10-dihydro-9,10-digallaanthracenes 1(alkyl: methyl) and 2 (alkyl: ethyl) were prepared by reaction of 1,2-di(chloromercurio)benzene with the corresponding trialkylgallium and isolated as colourless air- and moisture sensitive crystalline compounds. In the solid-state structure of 1 two slightly different monomers 1A and 1B are found, which form a dimer 1A 1B hold together by "medium" strong gallium arene π-interactions. urther weak π-interactions between 1A and 1A and 1B and 1B constitute a one-dimensional coordination polymer containing strands of the composition [ (1A 1B) (1B 1A) ] n. In contrast, compound 2 crystallizes in form of distinct molecular units without any further intermolecular π-interactions. The molecular units possess D 2d symmetry and are built by strong π-interactions between two digallaanthracene monomers. Two symmetrical aryl group bridges between two gallium atoms are observed for the first time in the subunits of 2. By addition of a Lewis-base (TH, Pyridine) to 2 a monomeric planar digallaanthracene framework is restored, as proven by an X-ray crystal structure analysis of 2 2 Py. The different structures of 1 and 2 are explained on the basis of steric effects.

15 Investigations in Chemical Vapor Deposition Systems of Silver Thomas Haase Physikalische Chemie 1, Universität Bielefeld, Universitätsstr. 25, Bielefeld L11 Silver is a promising candidate for the replacement of copper and aluminium as interconnect material because of its thermal and electrical properties. Chemical vapor deposition is a very good method to produce thin films and layers, however only few investigations have been reported regarding thin silver films. Suitable strategies require knowledge about the interplay of gas phase chemistry and surface chemistry. In this work, the gas phase of several newly synthesised silver(i) complexes has been analysed by temperature-programmed and in-situ mass spectrometry regarding on their volatility and thermal stability. The most promising precursors have been chosen for deposition experiments in a cold-wall reactor. Smooth and conductive silver films can be grown on glass substrates.

16 Invers-polarisierte Arsaalkene als Quelle hochreaktiver Arsinidene Philipp Bayer, Lothar Weber Anorganische Chemie II, akultät für Chemie L12 Aufgrund der geschwächten As=C-Doppelbindung in invers-polarisierten Arsaalkenen können diese Verbindungen leicht den Arsinidenbaustein R-As auf geeignete Moleküle übertragen. Phosphavinylidenkomplexe sind solche geeigneten Moleküle, da das Phosphoratom positiv polarisiert ist und somit der Addition des negativ-polarisierten Arsenatoms offen steht. Je nach Art des Substituenten am Arsenatom ergeben sich vielfältige Reaktionsprodukte, bei denen jedoch stets ein oder mehrere Arsinidenbausteine auf den Vinylidenkomplex übertragen werden. Als Beispiel einer solchen Reaktion sei die Umsetzung des errioarsaalkens 2 mit den Phosphavinylidenkomplexen 1a,b genannt [1]: OC M CO M= Mo: 1a M= W: 1b P C SiMe 3 SiMe 3 + OC e CO 2 As C Me 2 Me 2 OC M CO C P As e CO CO SiMe 3 SiMe3 3a,b [1] L. Weber, P. Bayer, H.-G. Stammler, B. eumann, Chem. Commun. 2005, 1595.

17 Organophosphorus π-conjugated systems: rom model molecules to functional materials Régis Réau Institut de Chimie de Rennes, UMR 6509, CRS-Université Rennes 1, rance M13 π-conjugated systems have attracted huge interest owing to their potential applications in electronic devices (e.g. light-emitting diodes, nonlinear optical materials ). Exploiting the unique properties of phospholes (low aromatic character, σ,π-conjugation), 1 we have developed a new family of π- conjugated oligomers and polymers 1 possessing low optical band gap. 2 The P-atom of phospholes exhibits a versatile reactivity allowing direct access to a range of new π-conjugated systems. These chemical modifications of the P-atom offer a way to diversify their electronic properties and are key issues for optoelectronic applications of phosphole-based materials (organophosphorus-containing OLED materials 3 and LO-phores 2 4 ). Lastly, chemistry of derivatives 3 exhibiting unusual σ- π conjugation will be described S P Bu 2 P S P Pd S S n P P S Bu S 3 1) M. HISSLER, P. W. DYER, R. REAU, COORD. CHEM. REV., 2003, 244, 1; 2) C. HAY, C. AVE, M. HISSLER, J. RAULT-BERTHELOT, R. RÉAU ORG. LETT., 2003, 19, 3467; 3) C. AVE, T-Y. CHO, M. HISSLER, C-W. CHE, T-Y. LUH, C.-C. WU, R. RÉAU J. AM. CHEM. SOC., 2003, 125, 9254; 4) C. AVE, M. HISSLER, K. SEECHAL, I. LEDOUX, J. ZYSS, R. REAU CHEM. COMMU, 2002, 1674; 5) C. AVE, M. HISSLER, T. KARPATI, J. RAULT- BERTHELOT, V. DEBORDE, L. TOUPET, L. YULASZI, R. REAU J. AM. CHEM. SOC., 2004, 136, 6058.

18 Synthesis of Efrapeptin Analogues for Conformational Studies Sven Weigelt and orbert Sewald Department of Chemistry, Bielefeld University, Bielefeld, Germany L14 The efrapeptins are a class of sequence-homologous peptide antibiotics (efrapeptins C-G) that are produced by the fungus Tolypocladium niveum. [1] They are inhibitors of 1 -ATPase, [2] show insecticidal and antiproliferative properties [3] and are active also against the malaria pathogen Plasmodium falciparum. [2] The efrapeptins are rich in α,α-dialkylated amino acids like Aib and contain an unusual cationic head group derived from leucinol at the C-terminus, while the - terminus is acetylated. Ac-Pip-Aib-Pip-Aib-Aib-Leu-β-Ala-Gly-Aib-Aib-Pip-Aib-Gly-Leu-Aib H ig. 1. Efrapeptin C Efrapeptin C was synthesized chemically for the first time by applying a convenient method for the introduction of Aib residues. The incorporation of the Aib residues succeeds smoothly using the highly reactive α-azido isobutyryl chloride followed by reduction of the resulting azido peptidyl resin to the amino peptidyl resin. The full sequence was assembled by a combination of solutionphase and solid-phase peptide synthesis steps with segment condensations. [4] The approach allows for the synthesis of a series of analogues required for biological and conformational studies. [5] ot only the synthesis of efrapeptins, but also the three-dimensional structure of these Aib-rich peptides is of importance for structure-activity relationship studies. Information about intramolecular interactions and distances between amino acid side chains is provided by modern MR methods. However, insufficient OE data may be obtained in the case of Aib-rich peptides. or structure determination in solution, OE experiments providing information about the distances e.g. between Aib methyl groups, are of particular importance. However, problems often occur in assigning the methyl group signals of the Aib residues in Aib-rich peptides. Aib residues, which are 2 H-labelled at the methyl groups may be introduced into peptides at welldefined positions in the amino acid sequence to get more concise MR-spectra. 2 H-labelled α- azidoisobutyryl chloride is conveniently synthesized in a six step procedure starting from acetone cyanohydrin-d 6 and can be used as D 6 -Aib equivalent. The degree of deuteration can be calculated to exceed 90% according to MR and MS data. [6] [1] a) S. Gupta, S. B. Krasnoff, D. W. Roberts, J. A. A. Renwick, L. S. Brinen, J. Clardy, J. Am. Chem. Soc. 1991, 113, ; b) S. Gupta, S. B. Krasnoff, D. W. Roberts, J. A. A. Renwick, L. S. Brinen, J. Clardy, J. Org. Chem. 1992, 57, [2] G. agaraj, M. V. Uma, M. S. Shivayogi, H. Balaram, Antimicrob. Agents Chemother. 2001, 45, [3] A. E. Papathanassiu (Ergon Pharmaceuticals LLC), U. S. Patent 2003, [4] M. Jost, J.-C. Greie,. Stemmer, S. D. Wilking, K. Altendorf,. Sewald, Angew. Chem. 2002, 114, ; Angew. Chem. Int. Ed. Engl. 2002, 41, [5] M. Jost, Synthese von Efrapeptin C und Efrapeptin-Analoga, Dissertation, Bielefeld University, Bielefeld [6] S. Weigelt,. Sewald, Synlett 2004, 4,

19 Kupferkomplexe von invers polarisierten Phosphaalkenen Jens Krümberg AK Prof. Dr. L. Weber Universität Bielefeld, Universitätsstr.25, D Bielefeld L15 Die Überbrückung von späten Übergangsmetallen durch Phosphanid-Ionen ist literaturbekannt. Die Umsetzung von Trimethylsilyldialkyl- oder -diarylphosphanen mit Kupfer(I)halogeniden führt häufig zu Metallclustern, deren zentrales Motiv ein Ring aus alternierenden Phosphor- und Kupferatomen ist. Von invers polarisierten Phosphaalkenen lassen sich ebenfalls zum Phosphanid isoelektronische Grenzstrukturen formulieren (B und C). R Me 2 P Me 2 + R Me 2 - P Me 2 R Me 2 - P Me + 2 A B C Es sollte also möglich sein, mit invers polarisierten Phosphaalkenen mehrere Metallzentren zu überbrücken. Bei der Reaktion von -P=C(Me 2 ) 2 mit Kupfer(I)chlorid bildet sich ein sechsgliedriger Ring aus drei Kupfer- und drei Phosphoratomen mit der ormel [(-P=C(Me 2 ) 2 )Cu] 3 Cl 3 1 wobei die Phosphanideinheit des Phosphaalkens jeweils zwei Kupferatome überspannt [1]. Cl (Me 2 ) 2 C Cu P P Cu Cl C(Me 2 ) 2 Cl Cu P C(Me 2 ) 2 1 Bei der Umsetzung von Me 3 Si-P=C(Me 2 ) 2 mit Kupfer(I)chlorid gelangt man zu einem roten unlöslichen eststoff, der die Zusammensetzung [(P=C(Me 2 ) 2 )Cu 2 Cl 2 ] n hat. Auch hier kann man eine Phosphorverbrückung von Kupferzentren vermuten. [1] L. Weber, J. Krümberg, H.-G. Stammler, B. eumann, Z. Anorg. Allg. Chem. 2004, 630, 2478.

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