ISMSC 2007 - Università degli Studi di Pavia

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PSA 55 Molecular Recognition of Carbohydrates: New Synthetic Tripodal Receptors Featuring Pyrrolic Binding Groups. Cristina Nativi, a,b Martina Cacciarini, a Oscar Francesconi, a Alberto Vacca, c Gloriano Moneti, d Andrea Ienco, e and Stefano Roelens. f a Dipartimento di Chimica Organica, b Centro Risonanze Magnetiche (CERM), c Dipartimento di Chimica, d Centro Interdipartimentale di Spettrometria di Massa (CISM), Universita` di Firenze, e Istituto di Chimica dei Composti OrganoMetallici (ICCOM), f Istituto di Metodologie Chimiche (IMC), Consiglio Nazionale delle Ricerche (CNR), Polo Scientifico e Tecnologico, I-50019 Sesto Fiorentino, Firenze, Italy. Carbohydrates are involved in many key processes in biological systems, like metabolism and transport, cell-to-cell adhesion, immune response, cell infection by pathogens and enzyme regulation. [1] All these processes are based on molecular recognition of carbohydrates, mainly exploiting H-bonding interactions. To understand the chemical basis of these phenomena, synthetic receptors mimicking the interaction between natural receptors and carbohydrates were widely employed. [2] However, the design of effective receptors for selective recognition of carbohydrates is yet an open challenge, for the achievement of which the comprehension of structural and functional requirements for recognition is a crucial issue. Among the multitude of artificial receptors reported in the chemical literature, benzene based tripodal structures have been often employed giving interesting results. Effective recognition requires the establishment of multiple binding interactions. In order to achieve the formation of an array of H bonds between the host and the saccharidic guest, we have designed a receptor architecture that O HO HO OH OR OH HN OH NH HN NH O HN H N HN H N HN HO HO HNOH NH HN OR combines both aminic and pyrrolic functional groups into an acyclic tripodal benzene-based scaffold. Indeed, aminic groups have been shown to be coordinatively complementary to hydroxyl groups, [3] while pyrroles are well-established H-bonding donors. [4] Their combination into a carefully designed architecture is thus believed to be effective for the recognition of carbohydrates. In this communication we wish to describe the synthesis and the binding properties of newly designed tripodal receptors, showing affinities for biologically relevant monosaccharides among the largest reported in literature for neutral synthetic H-bonding receptors. [1] B. Ernst, W. Hart, P. Sinay, Carbohydrates in Chemistry and Biology; Wiley-VCH: Weinheim, Germany, 2000. [2] A. P. Davis, T. D. James, In Functional Synthetic Receptors; T. Schrader, , A. Hamilton, D., Eds.; Wiley-VCH: Weinheim, Germany, 2005; pp 45-109. [3] S. Hanessian, M. Simard, S. Roelens, J. Am. Chem. Soc. 1995, 117, 7630 – 7645. [4] J. L. Sessler, P. A. Gale, W. S. Cho, Anion Receptor Chemistry, RSC Publishing, UK, 2006. Synthesis of Peptoid-containing Macrocycles by Multiple Ugi-type Multicomponent Reactions Daniel G. Rivera and Ludger A. Wessjohann* Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120, Halle/Saale, Germany. Fax: +49 345 5582 1309; Tel: +49 345 5582 1301; E-mail: wessjohann@ipb-halle.de PSA 56 A versatile strategy towards peptoid-containing macrocycles, termed multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs), has been recently developed. [1] In this approach, the building blocks are allowed to undergo a cyclooligomerization process based on multiple Ugi four-component reactions (Ugi-4CR) to afford macrocycles including varied peptoid moieties. [1] Macrocycles of different sizes, shapes, and presenting varied functional appendages have been produced in one pot by implementing the different combinations of bifunctional building blocks. [1,2] The rapid generation of skeletal and appendage diversity is a key feature of this approach, which enables the creation of parallel and combinatorial libraries of macrocycles with very low synthetic cost. [2] An extension of the MiB methodology to the third dimension allowed to obtain peptoidcontaining cryptands, cryptophanes, and steroid-based cages. [2a,3] This procedure comprises the performance of threefold Ugi-4CR-based macrocyclizations to assemble the macrobicyclic frameworks in one pot. The peptide-like skeletons and the variable functional appendages make these compounds amenable for applications in catalysis, coordination and supramolecular chemistry. [1] a) L. A. Wessjohann, B. Voigt, D. G. Rivera, Angew. Chem. Int. Ed., 2005, 44, 4785-4790; b) L. A. Wessjohann, E. Ruijter, Mol. Diversity, 2005, 9, 159-169. [2] a) D. G. Rivera, O. E. Vercillo, L. A. Wessjohann, Synlett, 2007, 308-312; b) L. A. Wessjohann, D. G. Rivera, F. Coll, J. Org. Chem., 2006, 71, 7521-7526. [3] D. G. Rivera, L. A. Wessjohann, J. Am. Chem. Soc. 2006, 128, 7122-7123.
PSA 57 Self-assembly of calixarene/CsI/diiodoperfluorocarbon supramolecular salts: structural studies and fluorous phase extraction Giuseppe Gattuso, a Andrea Pappalardo, a Melchiorre F. Parisi, a Pierangelo Metrangolo, b Giuseppe Resnati, b Tullio Pilati, c Sebastiano Pappalardo d a Dipartimento di Chimica Organica e Biologica, Università di Messina, salita Sperone 31, I-98166 Messina, Italy b DCMIC “G. Natta”, Politecnico di Milano, via L. Mancinelli 7, I-20131 Milano c CNR-ISTM, via C. Golgi 19, I-20133 Milano, Italy d Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, I-95125 Catania, Italy Inorganic, organic and perfluorinated compounds usually display a low affinity for each other. Recent studies have however demonstrated that formation of supramolecular aggregates driven by halogen bonding [1] between diiodoperfluorocarbons and iodide anions is possible, providing that ion-pairing effects (of the salt used) are outweighed by using an appropriate ionophore acting as a selective cation sequestering agent. [2] In this report we show that the self-assembly of hybrid supramolecular salts compounded of CsI, calixarenes, and diiodoperfluoroalkanes can be induced, both in the solid state and in solution, by harnessing a set of non-covalent forces. [3] In the solid state, the caesium ion is nested in the crown loop of the receptor, and shielded by a picolyl unit and a phenol ring involved in cation- interactions. The iodide anion, on the other hand, assembles into discrete aggregates held together by the concomitant action of hydrogen bonding (ethanol-iodide) and halogen bonding (diiodoperfluorocarbon-iodide). Single crystal X-ray analysis as well as 19 F NMR techniques show that the ‘naked’ iodide anion is a strong halogen bonding acceptor even in the presence of protic solvents. In keeping with these observations, we have used calixcrown 1 in conjunction with a number of (di)iodoperfluoroalkanes to force the selective uptake of caesium iodide from aqueous into fluorous phase. [1] P. Metrangolo, G. Resnati, Halogen bonding, Encyclopedia of Supramolecular Chemistry; Marcel Dekker, New York, 2004. [2] G. Gattuso, R. Liantonio, F. Meyer, P. Metrangolo, G. Resnati, A. Pappalardo, M. F. Parisi, T. Pilati and I. Pisagatti, Supramol. Chem., 2006, 18, 235–243. A. Casnati, R. Liantonio, P. Metrangolo, G. Resnati, R. Ungaro, and F. Ugozzoli, Angew. Chem. Int. Ed. 2006, 45, 1915– 1918. [3] G. Gattuso, A. Pappalardo, M. F. Parisi, I. Pisagatti, F. Crea, R. Liantonio, P. Metrangolo, W. Navarrini, G. Resnati, T. Pilati, S. Pappalardo, Tetrahedron, doi:10.1016/j.tet.2007.03.136. Properties of Deep-Cavity Cavitands Corinne L. D. Gibb, Srinivasan Kannupal, and Bruce C. Gibb* Department of Chemistry, University of New Orleans, New Orleans, LA, USA. PSA 58 We will discuss two aspects of our research into deep-cavity cavitands. In organic solvents, these bowl-shaped molecules readily form 1:1 complexes with suitable guest molecules (below left). We will report on the synthesis [1,2] and properties of cavitands possessing functionalized concavity that are capable of selectively reacting with complementary guests. We will also discuss water-soluble cavitands that form capsular complexes capable of entrapping one or more guests (2:1 complex shown below right).[3,4] We will report on some of the unusual properties of these complexes, and our recent efforts to understanding the thermodynamics driving their formation. [1] Kannupal, S.; Gibb, B. C., Org. Lett. 2007, 9, 745-748. [2] Laughrey, Z. R.; Gibb, B. C., J. Org. Chem 2006, 71, 1289-1294. [3] Gibb, C. L. D.; Gibb, B. C., Chem. Comm. 2007, Advanced Atricle (DOI: 10.1039/b618731e) [4] Gibb, C. L. D.; Gibb, B. C., J. Am. Chem. Soc. 2006, 128, 16498-16499.
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nd International Symposium on Macro
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Eric Anslyn University of Texas at
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1 Map of Salice Terme 7 5 6 3 9 2 8
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Symposium Program All sessions will
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11:40 - 12:00 Oral Presentation: V.
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PSA 22 Anion Receptors Based On The
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PSA 72 Molecular Tectonics: STM Stu
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PSB 11 Dual binding properties of p
Page 17 and 18: PSB 57 Removal Of Heavy Metal Ions
Page 19 and 20: 40 years of polyazamacrocycles. A p
Page 21 and 22: PL 5 Anion-Templated Assembly of In
Page 23 and 24: Exercising Demons: Synthetic Molecu
Page 25 and 26: Synthetic Strategies and Structural
Page 27 and 28: Anion binding as a conformational a
Page 29 and 30: Supramolecular control of a metal c
Page 31 and 32: OP 3 Control of molecular architect
Page 33 and 34: Catalyst discovery using dynamic co
Page 35 and 36: Cucurbit[n]uril Molecular Container
Page 37 and 38: OP 15 From non-mesomorphic nature t
Page 39 and 40: OP 19 Pyrrolic Tripodal Receptors f
Page 41 and 42: PSA 1 Efficient synthesis of pseudo
Page 43 and 44: Tetra-Cationic phthalocyanines Yasi
Page 45 and 46: PSA 9 Cell penetrating borosilica n
Page 47 and 48: PSA 13 Halide anion interactions wi
Page 49 and 50: Sensing with cavitands: Moving from
Page 51 and 52: Lead(II) complexation by calix[4]-h
Page 53 and 54: Functional [2×2] Grids Xiao-Yu Cao
Page 55 and 56: Neutral supramolecular systems inco
Page 57 and 58: PSA 33 Ratiometric Ion Sensors by R
Page 59 and 60: A photocontrollable receptor for Cu
Page 61 and 62: New emitters for mass spectrometric
Page 63 and 64: PSA 45 A fast-moving electrochemica
Page 65 and 66: Macrocyclic Porphyrin-Bidentate Che
Page 67: PSA 53 Electronic spectroscopy of e
Page 71 and 72: PSA 61 Piperazine Containing Polyam
Page 73 and 74: PSA 65 Synthesis of Self-Assembly S
Page 75 and 76: PSA 69 Assembly of Metallomacrocycl
Page 77 and 78: Supra-Biomolecular Tandem Assays -
Page 79 and 80: PSA 77 Synthesis and molecular reco
Page 81 and 82: PSA 81 Reaction of phthalic aldehyd
Page 83 and 84: Binding of perrhenate and pertechne
Page 85 and 86: PSA 89 Supramolecular assemblies of
Page 87 and 88: Polytopic Ligands for the Recovery
Page 89 and 90: PSB 1 Rosette Nanotubes as Scaffold
Page 91 and 92: PSB 5 Towards the development of ne
Page 93 and 94: PSB 9 A Quantitative [2]Rotaxane Sy
Page 95 and 96: Metal Complexes of the Polyether Io
Page 97 and 98: PSB 17 Metal controlled anion inter
Page 99 and 100: Crown Ether-tert-Ammonium Salt Comp
Page 101 and 102: PSB 25 A Minimalist Design for Self
Page 103 and 104: PSB 29 Control of Translation of th
Page 105 and 106: PSB 33 Multinuclear NMR, ESI MS and
Page 107 and 108: PSB 37 New Anthracene-based cycloph
Page 109 and 110: PSB 41 1,3,5-Tris(2-aminophenyl)ben
Page 111 and 112: Simple Isophthalamide Derivatives A
Page 113 and 114: PSB 49 On Sokolov’s approach to a
Page 115 and 116: PSB 53 New chromogenic sensors usin
Page 117 and 118: PSB 57 Removal of heavy metal ions
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PSB 61 Molecular Recognition of Ele
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PSB 65 Switching of Self to non-Sel
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Investigation of -cyclodextrin bind
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Novel ditopic probes for different
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PSB 77 Synthesis, supramolecular ar
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PSB 81 Tripodal polyamines as anion
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PSB 85 Templated Synthesis of Large
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PSB 89 Direct C-C coupling of 1,2,4
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PSB 93 The study of cytotoxicity ef
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PSB 97 Development of innovative so
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Campbell B. PSA 39 Campbell F. PSB
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Jensen L.G. PSA 82 Jeppesen J.O. IL
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Peters A.J. PSB 39 Peters A.J. PSB
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Sponsors of ISMSC 2007 The contribu
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