Molecular Recognition and Inclusion: Proceedings of the Ninth International Symposium on Molecular Recognition and Inclusion, held at Lyon, 7–12 September 1996

551 Pages·1998·25.31 MB·English

by  Raymond A. Dwek (auth.), A. W. Coleman (eds.)

MOLECULAR RECOGNITION AND INCLUSION
MOLECULAR RECOGNITION
AND INCLUSION
Proceedings ofthe Ninth International Symposium
on Molecular Recognition and Inclusion,
held at Lyon, 7-12 September 1996
Edited by
A. W. COLEMAN
Institut de Biologie et Chimie des Proteines,
CNRS,
Lyon, France
SPRINGER SCIENCE+BUSINESS MEDIA, B.V.
A c.I.P. Catalogue record for this book is available from the Library of Congress.
ISBN 978-94-010-6226-8 ISBN 978-94-011-5288-4 (eBook)
DOI 10.1007/978-94-011-5288-4
Printed on acid-free paper
AII Rights Reserved
© 1998 Springer Science+Business Media Dordrecht
Originally published by Kluwer Academic Publishers in 1998
Softcover reprint ofthe hardcover Ist edition 1998
No part of the material protected by this copyright notice may be reproduced or
utilized in any form or by any means. electronic or mechanical.
including photocopying. recording or by any information storage and
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TABLE OF CONTENTS
Introduction . ... . . .. . . . . . . . . . . . ... . . . . . . . . . .... . ... .. .......... .. ..... xv
Biological Importance of Glycosylation
R.A. Dwek ......... .. ....... . . . .... . . .. . . . . .. .... ....... . .. ........ .. . .
Hydration Interactions: Their Role in Recognition and Bioassembly Phenomena
F. Franks . . .. . . . . ... . . .... . . . .... .... ... . . . . ... . ..... .... . .. .. . . . . ... . 7
Tris(Macrocylcles) as Models for Transmembrane, Cation-Conducting Channels
G. W. Gokel, E. Abel, S.L. Dewall, J.P. Evans, T.J in, G.E.M. Maguire, E.S. Meadows,
O. Murillo, A. Nakano, M.R. Shah, I. Suzuki, G.P. Tochtrop and S. Watanabe 19
Construction of the Interfaces Possessing both Functionalities of Molecular
Recognition and Electron Transfer
T. Osa . . . ... . . ... . ......... . .. . ... . . . . . ... . .. . . . . .... . . ... . .. . . . .. . . . 29
Electrical Sieves for Molecule Recognition
C.L. Bowes, T. Jiang, A.J. Lough, G.A. Ozin, S. Petrov, A. Verma, G. Vovk,
D. Young and R.L. Bedard . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .3 .9 . . . . . . . . . . . . .
Supramolecular Complexation of Fullerenes and 1,2-Dicarbadodeca-Borane(12)
C.L. Raston . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59 . . . . . . . . . . . . . . . . .
Molecular Switches Based on Molecular Inclusion
D.N. Reinhoudt, A.M.A. van Wageningen and B.-H. Huisman ..... . . . .... . .. . . . . 67
Fluorescent Cyclodextrins as Chemosensors for Molecular Recognition
A. Ueno . ........ .. .. . .. .. ..... . . . . ... . . .. . . . . . . .... . . . .. . . .. .. . . . . . . 77
Tetrathiafulvalenes in Macrocyclic and Sypramolecular Chemistry: Self Assembly
with Tetrathiafulvalenes
J. Becher, Z. -H. Li, P. Blanchard, N. Svenstrup, J. Lau, M. Br¢ndsted Nielsen and
K.B. Simonsen . ....... . . . . ........ . .. . . . . . ... . . . . .. ... . .. . . ... . . . . . . . . 85
Anion Selective Recognition and Sensing by Novel Transition Metal Receptor
Systems
P.D. Beer . .. . . .. . . . .. . .. . . . . . . . ... . . . . . . . . . . . . . . . . . . . . . . . . . 97. . . . . . . . . .
Macrocyclic Sugar Thioureas: Cyclooligosaccharides Mimicking Cyclopeptides
J.M. Garcia Fernandez, C. Ortiz Mellet, J.L. Jimenez Blanco, J. Fuentes,
M. Martin-Pastor and J. Jimenez-Barbero . . ... . . ... . . . ... . ... . .. . . .. .. .... 103
vi
Molecular Clefts derived from Kagan's Ether. Synthesis and Solid State Inclusion
Complexes of a Chiral Molecular Tweezer
M. Harmata, M. Kahraman, S. Tygarajan, CL Barnes and C.l. Welch .... . ... . . 109
Molecular Tectonics: An Approach to Organic Networks
M. W. Hosseini .... .. ................. . . .......... . .................. . 117
New Macrocyclization Reaction based on Tris(2-aminoethyl)amine
1. lurczak, P. Lipkowski, D. T. Gryko and 1. Lipkowski . . . . . . . . . . . . . . . . .. . 1. 2.3 . . .
Signal Transmission by Artificial Receptors Embedded in Bilayer Membranes
1. -/. Kikuchi . .. .... .. . . ..... . .. ... . ... .. ..... . .. .. .... . ............ .. 129
Inclusion Compounds: Kinetics and Selectivity
L.R. Nassimbeni . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .1 3. 5. . . . . . . . . . . . . .
Kinetics of Intercalation in Lamellar Hosts using Time-Resolved X-Ray Diffraction
D. O'Hare, 1.S.O. Evans and S. Price . .... . ....................... . ...... . 153
Control of Permeation of Ions Across Vesicles and Chemical Differentiation of
Their Bilayer Membrane
P. Scrim in, F. Felluga, G. Ghirlanda, P. Tecilla, U. Tonellato and A. Veronese ... . 159
Molecular Recognition and Artificial Ion Channel with Amphiphilic Macrocycles
Y. Tanaka . . . ..... . ...... . .... . . . ... . .... . .. .. ... . .... .. ............. 167
Calix[4]-Bis-Crowns: From Nuclear Waste Treatment to Molecular Machines
Z. Asfari, B. Pulpoka, M. Saadioui, S. Wenger, M. Nierlich, P. Thuery, N. Reynier,
1. -F. Dozol and 1. Vicens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ... . .1 .7 .3 . . . . . . . .
Tripodal Coordination Complexes as Scaffolds for Molecular Recognition and
Catalysis
1. W. Canary, C.S. Allen, 1.M. Castagnetto, c.-L. Chuang, A.R. Lajmi, O. Dos Santos
and X. Xu ......... .. .......... . .... . ..... .. ..... . ...... . ... . ........ 179
Photochromic Molecular Recognition of Cyclodextrins Bearing Spiropyran Moiety
for Organic Guests
F. Hamada . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.8 .5 . . . . . . . . . . . . . . .
Interactions of Porphyrins with Cyclodextrins. Porphyrins as Probes for StUdying
Inclusion Phenomena
K. Kano, N. Tanaka and H. Minamizono . .. . .. ......... .. .. . . .. ..... . .... . . 191
Synthesis and Evaluation of New Ionoselective Materials
A. Favre-Reguillon, B. Dunjic, N. Dumont and M. Lemaire . . ... ... .... . .... . " 197
vii
Concave Reagents and Caralysts: From Lamps to Selectivity
U. Luning . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. . 2. 0.3 . . . . . . . . . . . . . .
Order-Disorder Phenomena in Inclusion Compounds: A Solid State NMR Study
S. Ternieden, J. Schmider and K. Muller . ... .... .. ... ... . . . . .... .. .. . .. . . . . 209
One Class of Azocalixarene, Different Types of Assemblies in Solid State
N. Ehlinger and M. Perrin . . . . .. ... . .. . . . . .. . . .. .... . ... . .. . . . . . ...... . . 215
The Simple Synthesis of Chiral Diazocoronands Derived from D-Mannitol and
L-Tartaric Acid
D. T. Gryko, P. Piqtek and J. Jurczak . . . .. .. .. ...... . . . ..... .. . . .... . . .. . .. 221
Biomimetic Oxidation of Aromatic Aldehydes Catalyzed by a
Bis(Coenzyme)-Cyclophane
P. Mattei and F. Diederich .... . .. . ...... . ....... . .. .. .. .. . ......... . . . . 227
Some New Calix[4]Arene-Based Complexing Agents
J. -B. Regnouf-de-Vains ....... . .... .... ..... . .... . ..... .... . . ....... . .. 233
Development of Ruthenium Probes Designed to Bind Enantio- and
Stereospecifically to DNA
R.S. Vagg, K.A. Vickery and P.A. Williams . . . . ... . ..... . .......... ...... . . . 239
Affinity for Both 5-HTta- and Dt-Receptors and Anxiolytic Activity of
N-(Arylpiperazinylalkyl)-Phthalimides
S.A. Andronati, T.A. Voronina, v.M. Sava, G.M. Molodavkin, S. Yu. Makan and
S. G. Soboleva . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. .. .2 .4 .5 . . . . . . . . . . . .
Physico Chemical Studies of the Adsorption Process Between Animated Silica
Wafers and Oligonucleotides
V. Balladur, B. Mandrand and A. Theretz . . . . .... . . .. ... . . . ..... . . . . . ... . . . 251
How Can X-Ray Structures Be Helpful for Design of Ionophores for Ion-Selective
Membrane Electrodes?
J.F. Biernat and E. Luboch . . .. . ..... .. . ... .. . . . . ..... .... . ........... . . 255
The Synthesis and Conformational Analyses of Some Dibenzo[3n+2]Crown-n
Ethers
N. Bozkurtoglu and 9. Erk .. . ....... . .. . . .. . . . . .... . . ... ........ . .... . .. 259
Calix[4]Resorcinarene Derivatives as Ionophores for Cations Studied in
Polymeric (PVC) Membrane
Z. Brz6zka, E. Liszewska, M. Pietraszkiewitcz and R. G!jSiorowski . . . .. ... ...... 263
Synthesis of Isoflavone Derivatives of Crown Ethers
M. Bulut, B. YIlmaz and 9. Erk .. ... . . . .. .. . .. . . .... ... ..... . ...... .. .. . . 267
Vlll
The Synthesis of Some Coumestan and Related Chromogenic Derivatives of
Crown Ethers, Part II
M. Bulut and 9. Erk ................................................... 271
The Association Constants of Macrocyclic Ether-Cation Interactions in Dioxane /
Water Mixtures, Part II
o. 9akJr, B. Prek and r Erk ..... ... . . .......... . . . . . . . . . . . . . . . ... . 2. 75. . .
Binuclear Copper (II) Complexes of Cyclo-Bis Intercaland Receptors. Effect of the
Ligand on the Crystal Structure and Complexation Properties
M. Cesario, J. Guilhem, e. Pascard, M.-P. Teulade-Fichou, M. Dhaenens,
J. -Po Vigneron and 1. -M. Lehn . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. 7. 9. . . . . . . . .
Specific Interaction of ~-Casomorphin (Human) with Cu(II) Ion
E. Chruscinska, G. Micera, D. Sanna and W. Ambroziak . . . . . . . . . . . . . . ... . 2. 83. . .
The Structure and Properties of the New Ligand for the 5-HT1A Receptors
Yu.M. Chumakov, G. Bocelli, A. Cantoni, M. Gdaniec, V.M. Sava and
S. G. Soboleva .... . .................................................. 291
Phase Transitions of Cyclophosphazene Adducts Directly Followed by
Solid-State NMR
A. Comotti, R. Simonutti, M. e. Gallazzi and P. Sozzani ... .. ..... . ............ 297
Molecular Recognition in Solid Inclusion Compounds of Novel Roof-Shaped
Diol Hosts
I. Csoregh and E. Weber ................................. . ............. 301
Success Rate in a Chiral Separation: Towards a Better Separation Machinery
M. Czugler, E. Weber and P.P. Korkas ...................... . ............. 305
NMR Study of Per(3,6-Anhydro) IX Cyclodextrin as a Potential Agent for the
Biological Decontamination of Lead as Evidenced by NMR Spectroscopy
J.e. Debouzy, F. Fauvelle, A. Gadelle, B. Perly and e. Baudin ................. 309
Thioureido p-Cyclodextrins as Molecular Carriers for the Anticancer Drug
Taxotere®
J. De/aye, e. Ortiz Mellet, 1.M. Garcia Fernandez and S. Maciejewski . .......... 313
Continuity and Discontinuity in the Thermodynamic Properties of Solid
p-Cyclodextrin Versus Hydration. A Comparative Study
e. De Brauer, M. Diot, P. Germain and 1.M. Letoffe ......................... 317
Phosphorylated Cavitands: Encapsulation of Hard Cationic Guests
P. Delanghe, 1.-e. Mulatier and J.-P. Dutasta ..... .. ....................... 321
ix
The Cation Complexation Properties of Per-3,6-Anhydro-a and p-Cyclodextrins
Studied by Thin Layer Chromatography and IH NMR
F. Fauvelle, A. Gadelle, J.C Debouzy and B. Perly .. .. . .. ... .. . ... . . .. . .. . .. 325
Caesium-Selective Imprinted Phenolic Resins
A. Favre-Reguillon, B. Dunjic, N. Dumont and M. Lemaire . .. . .. . ........ . .... 329
Supramolecular Synthesis with Carboxyl-Substituted Secondary Dialkylarnmonium
Salts and Macrocyclic Polyethers
M.C T. Fyfe, J.F. Stoddart, A.N. Collins..t;md DJ. Williams . .................. . 333
Cation Binding of Benzo Crown Ethers in Acetonitrile Using Fluorescence
)pectroscopy, Part II
l. Got;men and 9. £rk . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. . 3.3 7. . . . . . . . . . . .
:rystal Engineering with Novel Arninoborates. Hydrogen-Bonded Cyclic Motifs
Containing Tetrahedral Boron and Nitrogen
Z. Goldschmidt, S. Levinger, I. Ben-Arie, S. Alfi and S. Cohen . ..... . .......... . 341
Novel Bis(Phenoxyalkyl)Sulfane Podands - Synthesis and Complex Formation
with Thiophilic Metals Ions
B. Habermann, T. Krilger, H. Stephan, K. Hollmann and K. Gloe . . . . . . . . . . . 3. 4. 5. .
Design of Coordination Arrays as Potential Molecular Memory Units and Switches
G.S. Hanan, U.S. Schubert, D. Volkmer, J.-M. Lehn, J. Hassmann, CY. Hahn,
O. Waldmann, P. Milller, G. Baum and D. Fenske .. .... .... ............... . . 349
Synthesis of a Functionalized Chiral Molecular Tweezer
M. Harmata and S. Tyagarajan . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3. 5.3 . . . . . . . . . . .
Optimal Polymer Architecture for Adsorption at the Solid-Liquid Interface:
Dendrimers Versus Linear Polymers
A. Hopkinson .. .. . .... . .. . . .. . .... . .. ... ........ .. . . .. . .. . ......... .. 357
Organizations of Two-Dimensional DNA-Mimetics at the Air-Water Interface
K. [jiro, F. Nakamura and M. Shimomura . .. . . ........ . . .. . .. . . . . . . . . . .. ... 361
Metal-Induced "Aggregation-Deaggregation" and "Colour Change" in FulJerene
Derivatives
A. Ikeda and S. Shinkai .. ... . ........ . . . . . .... . .. . . . .. .. . . . .. . . .... .... 365
Allosteric Regulation in the Catalytic Activity of Cyclodextrin Dimer as an
Artificial Hydrolase
H. Ikeda, S. Nishikawa, A. Ueno and F. Toda ... ... ... ... . . .. ......... ...... 369
x
Confonnational Studies on Athryl(Alkylamino)-p-Cyclodextrin Complexes and
Their Abilities as DNA Intercalators
T. Ikeda. A. Nakazato. M. Mori. A. Veno. F. Toda and H.-i. Schneider . . . . ...... . 373
Host-Guest Complexation of Phosphorus Contained Calixarenes with Aromatic
Molecules in RP HPLC Conditions. The Stability Constants Detennination
0.1. Kalchenko. i. Lipkowski. R. Nowakowski. V.I. Kalchenko. M.A. Vysotsky and
L.N. Markovsky . . ... . . . ....... .. .... . . . ... ... .. ... ................... 377
Synthesis of Cyclodextrins Derivatives Carrying Bio-Recognisable Saccharide
Antennae
R. Kassab and H. Parrot-Lopez . ............... . .. . ........... . ... . ... . .. 381
X-Ray and Atomic Force Microscopy Structures of Short Chain Amphiphilic
Cyclodextrins
/. Nicolis. A. W. Coleman. M. Selkti. M. Munoz. A. Kasselouri. S. Alexandre.
i.-M. Valleton. P. Charpin and C. de Rango .................. . . . ... . . . . . ... 385
Study of Inclusion of Cobalt(II) in Per-6-0-(Ter-Butyl Dimethylsilyl) ~-CD Using
Pyrene as a Fluorescence Probe
A. KilSselouri. P. Prognon. A. W. Coleman and G. Mahuzier ... . ..... . . . . . . . ... 391
~-Cyclodextrin Complexes of Polymers Containing Aromatic Groups
L. Leclercq. M. Bria. M. Morcellet and B. Martel. . . . . . . . . . . . . . . . . . ... . 39. 5. . . . .
Inclusion of Neutral Guests in a Self-Assembling Superstructure
S.B. Lee and 1.-1. Hong .... .... . . .. ............ . ...... . ............... . 399
Recognition and Transport of Nucleoside Monophosphates with Synthetic
Receptors
S.B. Lee. Y.-G. lung. w.-S. Yeo and l.-/. Hong . ... .. .................. .. .. .. 403
Structure and Dynamics of Guest Molecules in Cyclophosphazene Inclusion
Compounds
A. Liebelt. i. Schuhmacher and K. Muller. . . . . . . . . . . . . . . . . . . . . .. .. . .4 .0 .7 . . . . .
Towards Rotaxane-Based Metal-Ion Sensors
O.A. Matthews. J.F. Stoddart and N.D. Tinker 411
Microcalorimetric Studies of Ligand-Induced Vancomycin Dimerisation and
Molecular Recognition
D. McPhail and A. Cooper ..... . .... ... ... .. ....... . . . . . ........ . . . . . .. 415
Self-Assembled Hydrogen Bonded Dimers of Calix[4]Arenes
O. Mogck. V. Bohmer. M. Pons. E.F. Paulus and W. Vogt .... ..... ............ 419
xi
Crystal Growth of Macrocycles in Gel
L. Motta Viola, N. Ehlinger and L. Grosvalet . . . . . . . . . . . . . . . . . . . . . .. . 4.2 3. . . . . .
Chiral Calixarenes Functionalized with Camphorsulfonyl Groups. Synthesis,
Structure and Inclusion Properties
L. Motta Viola, f.-B. Regnouf de Vains, C. Bavoux and M. Perrin . ........ .... .. 427
Synthesis of Water Soluble Resorcinarenes Application in
Nanofiltration-Complexation
L. Nicod, E. Gaubert, H. Bamier and M; Lemaire ...... . ...... . .... . . .. ..... 431
Crystal Engineering in Solid-State Metal Salt Complexes of Cyclodextrins
I. Nicolis, M. Eddouadi, A. W. Coleman, M. Selkti, F. Villain and C. de Rango . .... 435
Glycolipid Hydrolase Models. D, L-Stereorecognition of Amino Acids
Y. Ohkatsu and M. Ozawa ... . ........... ... ...... . ...... . . ...... .... . .. 439
Anthracene-Crown Ethers: Synthesis and Complexation of Selected Cations
R. Ostazewski . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. .4 .4 .3 . . . . . . . . . . . . .
Cyclo Bis-Intercaland Receptors: Structure of Two Interactive Inclusion Complexes.
Stability of the Hydration Network Facing Two Different Substrates
T. Paris, f .-P. Vigneron, f.-M. Lehn, M. Cesario, L. Tchertanov and f. Guilhem 447
Zeolites as Catalysts: Porosity or Acidity? Alkylation of Benzene
G. Perez, 0. Ursini and E. Lilla ......................................... 451
Quantification of Specific Immunological Reactions by Atomic Force Microscopy
A. Perrin and A. Theretz . .. . .... .. ..... . ....... . ..... . .. . .......... .... 455
Transport Studies of Inorganic and Organic Cations Across Liquid Membranes
Containing Mannich-Base Calix[4]Resorcinarenes
O. Pietraszkiewicz, M. Komial and O. Pietraszkiewicz ... .... ......... . ...... 459
Chiral Recognition Studies of Amino Acids by Chiral Calix[4]Resorcinarenes in
Langmuir Films
M. Pietraszkiewicz, P. Prus and W. Fabianowski ... . . .. ..... . . . . .... ........ 463
Preorganized Macrocyclic Dicarboxylic Receptors. Synthesis, Inclusion Behaviour
and Structural Study
R. Pollex, E. Weber and M. Czugler ........... . ................... ... . . . . 467
New Endo-Functional Cryptophanes as Selective Complexants
c.E.O. Roesky, M. Czugler, E. Weber, T. Kruger, H. Stephan and K. Gloe ........ 471