14th International Symposium on Chirality
Final Programme ISCD 14
Symposium Site:
Faculty of Chemistry, University of Hamburg,
Martin-Luther-King-Platz 6, 20146 Hamburg
Sunday, September 8, 2002
10.00 am – 4.00 pm
Short Course 1:
Recent advances in analytical application of circular
dichroism (CD) and HPLC-CD
Instructors: Nina Berova, Albrecht Mannschreck
Short Course 2:
Enantioselective gas chromatography:
Applications in stereochemical analysis and
preparation of pure enantiomers
Instructors: Markus Juza, Wilfried A. König,
Graeme J. Nicholson, Volker Schurig
2.00 pm – 6.00 pm
Registration
6.00 pm
ISCD-14 Opening Ceremony (Lecture Hall A)
(Chair: D. Misiti, G. Blaschke, V. Schurig, W. A. König)
Presentation of the "Chirality Medal"
Chirality Medal Award Lecture:
Dieter Seebach, Organic Chemistry Laboratory, Swiss
Federal Institute of Technology (ETH), Zurich/Switzerland:
Synthesis, Structure and Biological Properties of β-Peptides
- A World Full of Chirality
8.00 pm – 10.00 pm
8
Welcome Party
(Complimentary to all symposium attendees)
14th International Symposium on Chirality
Monday, September 9, 2002
9.00 am
Welcome Addresses
Plenary Session 1
Origin of Homochirality
Chair: G. Blaschke, V. Schurig
9.15 am- 10.00 am
B. Feringa, University of Groningen/The Netherlands,
Control and Amplification of Chirality
10.00 am- 10.45 am
M. Lahav, I. Weissbuch, H. Zepik, E. Shavit, K. Kjaer, G.
Bolbach, L. Leiserowitz, The Weizmann Institute of Science,
Rehovot/Israel; Risø National Laboratory/Denmark;
Université Pierre et Marie Curie/France, Chiral Amplification
of Oligopeptides with 2-dimensional Crystalline Assemblies
at the Air/Water Interface
10.45 am – 11.15 am
Coffee Break
Chair: P. Margaretha
11.15 am – 12.00
J. R. Scheffer, University of British Columbia/Canada, In
the Footsteps of Pasteur: Asymmetric Induction in the
Photochemistry of Crystalline Ammonium Carboxylate Salts
12.00
R.M. Pagni, F. Goa, D. Boyles, R. Sullivan, R.
Compton, University of Tennessee/USA, The
Photochemistry of 2-Iodooctane in Solution and the Gas
Phase. The Search for a New Type of Asymmetric
Photochemistry
- 12.15 am
12.15 pm – 1.00 pm
1.00 pm – 2.00 pm
Lunch Break
Poster sessions A, B – Exhibition –
Vendor Seminars
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14th International Symposium on Chirality
Plenary Session 2
Part 1
Chiral Selectors, Enantiomer Separation I
Chair: E. Francotte
2.00 pm – 2.30 pm
D. Armstrong, Iowa State University/USA, Enantiomer
Separation of Biologically Active Coumarine Derivatives and
Related Compounds
2.30 pm – 3.00 pm
N. M. Maier, W. Lindner, University of Vienna/Austria, A
Combinatorial Approach to Enantioselective Receptors for βAmino Acid Derivatives
3.00 pm – 4.00 pm
Coffee Break – Poster sessions C, D, E- Exhibition
Parallel Sessions (Session 2, Part 2 and Session 3)
Session 2, Part 2
Chiral Selectors, Enantiomer Separation I
Chair: D. W. Armstrong, Y. Okamoto
4.00 pm – 4.15 pm
M. Driffield, D. M. Goodall, A. S. Klute, D. K. Smith,
University of York/UK; Pfizer Global Research/UK, Novel
Chiral Stationary Phases for HPLC based on dendritic
Branching
4.15 pm – 4.30 pm
L. Thunberg, S. Allenmark, University of
Göteborg/Sweden, Studies of C2-Symmetric Chiral Selectors
and their Use in Design of Stationary Phases in Liquid
Chromatography
4.30 pm – 4.45 pm
R. Duval, CHIRALSEP S. A./France, Macrochiral Cavities
Crosslinked in a Three-Dimensional Polymeric Network as
New Selectors for Chiral Stationary Phases
4.45 pm – 5.00 pm
J. Oxelbark, University of Göteborg/Sweden, Benzoylated
Tartaric Acid Derivatives as Chiral Selectors. Effects from
Amide Hydrogen Bonding and Conformational Rigidity
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14th International Symposium on Chirality
Session 3
Enantioselective Synthesis I
Chair: Gy. Szöllösi, V. V. Borovkov
4.00 pm – 4.15 pm
M. J. Okasinski, M. F. Doherty, University of
California/USA; Air Products and Chemicals/USA,
Simultaneous Kinetic Resolution of Propylene Oxide and
Propylene Glycol in a Continuous Reactive Distillation
Column
4.15 pm – 4.30 pm
A. S. K. Hashmi, M. A. Grundl, F. Naumann, A. Rivas Nass,
J. W. Bats, University of Stuttgart/Germany, Synthesis and
Properties of Enantiomerically Pure Metallacycloalkanes
4.30 pm – 4.45 pm
A.V. Korostylev, K. N. Gavrilov, O. G. Bondarev, A. I.
Polosukhin, V. N. Tsarev, N. E. Kadilnikov, S. E. Lyubimov,
A. A. Shiryaev, S. V. Zheglov, H.-J. Gais, V. A. Davankov,
Ryazan State Pedagogic University, Ryazan/Russia, Institute
of Organoelement Compounds, Moscow/Russia, University
of Aachen/Germany, Novel P,N-Bidentate Phosphite Ligands
in Asymmetric Catalysis
Plenary Session 4
Topological Chirality, Supramolecular Systems
Chair: B. Chankvetadze, M. Lahav
5.00 pm – 5.45 pm
F. Vögtle, S. Buschbeck, J. Recker, A. Böhmer, O. Lukin, G.
Pawlitzki, University of Bonn/Germany, Topological
Chirality of Catenanes, Rotaxanes and Molecular Knots
5.45 pm – 6.00 pm
N. Solladié, M. Gross, Ch. Sooambar, V. Troiani, Université
Louis Pasteur et CNRS/France, Extended Multi-Porphyrinic
Architectures with Enantio-pure Linkers
6.00 pm – 6.15 pm
V.V. Borovkov, Y. Inoue, R. Kuroda, Osaka University and
ERATO JST/Japan, Phase Transition Control of
Supramolecular Chirality Induction in Bis(Zinc Porphyrin)
6.15 pm – 6.30 pm
S. Shinoda, T. Nishimura, H. Tsukube, Osaka City
University/Japan, Chirality Induction of Octadentate Sodium
Complex via Supramolecular Interaction with Chiral
Aggregate
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14th International Symposium on Chirality
Tuesday, September 10, 2002
Plenary Session 5
Part 1
Pharmaceutical Relevance of Chirality
Chair: I. Agranat, A. W. Frahm
8.30 am – 9.15 am
J. Caldwell, Imperial College/UK, Enhancing
Drug Therapy by Putting Chirality to Work
9.15 am – 10.00 am
H.-J. Federsel, Astra Zeneca/Sweden, Facing Chirality in
the 21st Century: Approaching the Challenges in the
Pharmaceutical Industry
10.00 am – 10.30 am
Coffee Break
Parallel Sessions (Session 5, Part 2, and Session 6)
Session 5, Part 2
Pharmaceutical Relevance of Chirality
Chair: J. Caldwell, H.-J. Fedsersel
10.30 am – 10.45 am
H. Caner, I. Agranat, The Hebrew University of
Jerusalem/Israel, Aspects of Stereochemistry of the Gastric
Proton-Pump Inhibitor Esomeprazole
10.45 am – 11.00 am
P. Bisel, E. Breitling, A. W. Frahm, University of
Freiburg/Germany, The Stereoisomeric
2,3Butanoglutamic Acids: Conformationally restricted
Glutamate Analogues
11.00 am – 11.15 am
M. Juza, CarboGen Laboratories/Switzerland,
Enantioselective Chromatographic Separations in the
Pharmaceutical Industry - Problems, Solutions, and
Surprises
J. Gal, University of Colorado/USA,
Chirality as reflected in Philately
11.15 am – 11.30 am
11.30 am – 12.00
12
J. Gal, J. G. Gerber, S. G. Filler, University of
Colorado/USA and Harbor-UCLA Res. and Ed. Inst./USA,
Overview of Chirality in Azole Antifungal Drugs and New
Results on the Inhibition of CYP3A4 by Ketoconazole and
Itraconazole
14th International Symposium on Chirality
Session 6
Enantioselective Sensors
Chair: S. Allenmark, F. Toda
10.30 am – 10.45 am
R. Corradini, C. Paganuzzi, R. Marchelli, S. Pagliari, S.
Sforza, A. Dossena, G. Galaverna, A. Duchateau, Parco Area
delle Scienze/Italy and DSM Research/The Netherlands,
Design and Synthesis of Fluorescent β-Cyclodextrins for the
enantioselective Sensing of Amino Acids
10.45 am – 11.00 am
K. Hirose, T. Nakamura, R. Nishioka, T. Ueshige, Y. Tobe,
Osaka University/ Japan, Sumika Chemical Analysis Service/
Japan, Preparation and Evaluation of Novel Chiral
stationary Phases Covalently Bound with Chiral pseudo-18Crown-6-ethers
11.00 am – 11.30 am
E. Yashima, K. Maeda, O. Sato, M. Watanabe, Nagoya
University/Japan, Switching of a Macromolecular Helicity
for visual Distinction of Molecular Recognition Events
11.30 am – 12.00
J. W. Canary, New York University/USA, Molecule-Based
Sensing facilitated by Ligand Stereochemical Control and
Chiroptical Detection
12.00
- 2.00 pm
Lunch Break – Exhibition - Vendor Seminars
Plenary Session 7
Part 1
Enantiomer Resolution by Crystallization
Chair: B. Feringa, J. Scheffer
2.00 pm – 2.30 pm
F. Toda, Okayama University of Science/Japan, Chiral
Recognitions and Reactions in Inclusion Crystals
2.45 pm – 3.15 pm
R. Kuroda, T. Harada, The University of Tokyo and
ERATO JST/Japan, Chirality in the Solid State: Application
to Crystal Chirality of Inorganic Salts and Films of Proteins
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14th International Symposium on Chirality
3.15 pm – 3.45 pm
R. Tamura, D. Fujimoto, Z. Lepp, H. Takahashi, T. Ushio,
Kyoto University and Taiho Pharmac. Comp./ Japan,
Mechanism of Preferential Enrichment, an unusual
Enantiomeric
Resolution
Phenomenon
caused
by
Polymorphic Transition
3.45 pm – 4.15 pm
T. R. Vries, K. Pouwer, B. Kaptein, Syncom BV and
DSM/The Netherlands, Dutch Resolution
4.15 pm - 4.45 pm
Coffee Break
Parallel Sessions (Sessions 7, Part 2 and Session 8)
Session 7, Part 2
Enantiomer Resolution by Crystallization
Chair: A. Mannschreck
4.45 pm – 5.00 pm
J. W. Nieuwenhujzen, T. R. Vries, R. M. Kellog, K.
Pouwer, R.F.P. Grimbergen, C. Koopman, B. Kaptein, Q. B.
Broxterman, L. A. Hulshof, Syncom BV and DSM/The
Netherlands, Understanding Dutch Resolution: Nucleation
Inhibition ?
5.00 pm – 5.15 pm
R. Purrello, R. Lauceri, A. Raudino, L. Monsù Scolaro, N.
Micali, University of Catania, University of Messina, ISSN
CNR and ITS CNR/ Italy, From Achiral Porphyrins to
Imprinted Chiral Aggregates and further.
Self-Replication
of Chiral Memory from Scratch
Session 8
Calculation Methods, Modeling
Chair: F. Gasparrini
4.45 pm – 5.00 pm
P. J. Stephens, F. J. Devlin, J. R. Cheesman, M. J. Frisch,
University of Southern California and Gaussian Inc./USA,
Determination of absolute Configuration using ab initio
Calculations of Optical Rotation
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14th International Symposium on Chirality
5.00 pm – 5.15 pm
H. Dodziuk, W. Koźminski, G. Dolgonos, Polish Academy
of Sciences/Poland, Cooperativity of 1 : 2 complex
formation of camphor enantiomers with α-Cyclodextrin. An
unusual "isotope effect".
5.15 pm – 6.00 pm
Exhibition
7.00 pm – 11.30 pm
Symposium Bankett on Riverboat "MS Hamburg"
(embarking St. Pauli Landungsbrücken 6 - 9)
Wednesday, September 11, 2002
Plenary Session 9
Part 1
Chirality in Biological Systems
Chair. W. Francke
8.30 am – 9.15 am
G. Fráter, Givaudan Dubendorf/Switzerland,
Importance of Chirality in Fragrance Chemistry
9.15 am –10.00 am
W. Kitching, The University of Queensland/Australia, Insect
Chemistry and Chirality
10.00 am – 10.30 am
The
Coffee Break
Parallel Sessions (Sessions 9, Part 2 and Session 10)
Session 9, Part 2
Chirality in Biological Systems
Chair: G. Fráter, W. Kitching
10.30 am – 11.00 am
H. Oikawa, T. Sassa, Hokkaido University and Yamagata
University/Japan, Biosynthesis of Diterpene Aphidicolin:
Study on a Key Enzyme for Construction of the Aphidicolane
Skeleton
11.00 am – 11.15 am
T.G. Köllner, C. Schnee, J. Gershenzon, J. Degenhardt,
Max-Planck-Institute for Chemical Ecology/Germany, The
Stereospecificity of two Maize Sesquiterpene Synthases is
dependent on Four Amino Acids in the Active Center
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14th International Symposium on Chirality
11.15 am – 11.30 am
H. J. Bouwmeester, I. G. Altug, C. O. Schmidt, M. Beale,
W. A. König, Plant Research International/The Netherlands,
Long Ashton Res. Station /UK and University of
Hamburg/Germany, Enantioselectivity of Plant Enzymes. The
Characterization of a (+)- and a (-)-Germacrene D Synthase
cDNA from Solidago Canadensis
11.30 am – 11. 45 am
S.
Schulz,
C.
Arsene,
Techn.
Univers.
of
Braunschweig/Germany, Determination of the Absolute
Configuration of Long-Chain Acetogenins by Degradation or
Chiral Derivatization
Session 10
Enantioselective Synthesis II
Chair: F. Henin, Th. Wenzel
10.30 am – 11.00 am
O. McConnell, A. Bach, V. Marathias, J. Mattes, D. Herold,
E. Kerns, L. Di, M. Y. Zhang, K. Fan, M. Kagan, C. Kraml,
K. Keating B. Marquez, D. Ho, Wyeth Res. and Princeton
University/USA, Chiral Separation and Determination of
Absolute Stereochemistry of Chiral Molecules in Drug
Discovery
11.00 am – 11.15 am
C. Wolf, P. A. Hawes, Georgetown University/USA, A High
Throughput Screening Protocol for Fast Evaluation of
enantioselective Catalysts
11.15 am – 11.30 am
Y. Takeuchi, Z. Liu, Toyama Med. and Pharmac. University/
Japan, Development of Chiral N-Fluorosultam fluorinating
Agents and their Application in Medicinal Chemistry
11.30 am – 11.45 am
Z. Czarnocki, A. Siwicka, Warsaw University/Poland,
Stereoselective Synthesis of some Tetrahydroisoquinoline and
β-Carboline Derivatives
11.45 am – 1.00 pm
1.00 pm - 2.00 pm
Lunch Break
Poster sessions F, G -Exhibition
Vendor Seminars
16
14th International Symposium on Chirality
Plenary Session 11
Chiral Selectors, Enantiomer Separation II
Chair: V. Davankov, W. Lindner
2.00 pm – 2.45 pm
E.R.
Francotte,
Novartis
Pharma/Switzerland,
Enantioselective Liquid Chromatography:
A Mature
Separation Technology?
2.45 pm – 3.15 pm
Y. Okamoto, C. Yamamoto, T. Kubota, Nagoya
University/Japan, Polysaccharide Derivatives as Potential
Chiral Stationary Phases for HPLC
3.15 pm – 3.45 pm
B. Chankvetadze, University of Münster/ Germany,
Enantioseparations
in
Capillary
Electromigration
Techniques
3.45 pm – 4.00 pm
C. Suteu, G. Cox, Chiral Technologies/France and USA,
Polysaccharides-based
Stationary
Phases
for
Chromatography. From Analytical to Manufacture of Chiral
Drugs
4.00 pm – 4.30 pm
Coffee Break
Plenary Session 12
Chiroptical Phenomena I
Chair: J. Gawronski, K. Nakanishi
4.30 pm – 5.00 pm
N. Berova, X. Huang, G. Pescitteli, N. Fujioka, G. Proni, K.
Nakanishi,
Columbuia
University/USA,
Dimeric
Metalloporphyrin Hosts for Chiral Recognition monitored by
Circular Dichroism
5.00 pm – 5.30 pm
A. Mannschreck, R. Kiesswetter, University of
Regensburg/Germany, Polarimetric or Circular Dichroic
Detection during Enantioselective Liquid Chromatography
5.30 pm – 5.45 pm
S. Abbate, E. Castiglioni, R. Gangemi, F. Lebon, G. Longhi,
University of Brescia and ECS/Italy, Vibrational Circular
Dichroism Spectroscopy in the Near-Infrared: Experiments
and Theory
5.45 pm - 7.00 pm
Poster sessions H, I, J
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14th International Symposium on Chirality
Thursday, September 12, 2002
Plenary Session 13
Discrimination of Enantiomers by NMR and Mass
Spectrometry
Chair: A. Solladie-Cavallo, Ch. Wolf
8.30 am – 9.00 am
Th. Wenzel, Bates College/USA, Lanthanide-Chiral
Solvating Agent Couples as Chiral NMR Shift Reagents
9.00 am – 9.30 am
H. Ohrui, K. Imaizumi, K. Akasaka, Tohoku University /
Japan, Further Study on Discrimination of Remote Chirality
9.30 am – 9.45 am
H. Navrátilová, M. Potáček, Masaryk University / Czech
Republic
Trans-4-(4-fluorophenyl)-3-substituted 1-Methylpiperidines:
Chiral Recognition and Transformations
9.45 am – 10.00 am
M. Shizuma, Y. Takai, M. Sawada, Osaka Municipal Techn.
Res. Inst./Japan, Evaluation of optical Purity of chiral
Amines by FAB Mass Spectrometry
10.00 am – 10.15 am
S. Miyano, F. Narumi, N. Matsumura, N. Morohashi, N. Iki,
Ishinomaki Senshu University/Japan, Inherently chiral
1,2-Thiacalix[4]crown-4 derivatives and their Chiral
Discrimination Ability
10.15 am – 10.45 am
Coffee Break
Parallel Sessions (Session 14 and Session 15)
Session 14
Chiral Selectors, Enantiomer Separation III
Chair: L. Blomberg, H. Hühnerfuss
10.45 am – 11.00 am
C. Minguillón, P. Franco, J. Blanc, W. R. Oberleitner, N. M.
Maier, W. Lindner, University of Barcelona/Spain and
University of Vienna/Austria, Centrifugal Partition
Chromatography (CPC) in the preparative Separation of
Enantiomers using Cinchona Alkaloid Derivatives as Chiral
Selectors
18
14th International Symposium on Chirality
11.00 am – 11.15 am
J. Theobald, Novasep/France, Chiral Chromatographic
Separation: An Actual Challenging Tool for the
Pharmaceutical Industry
11.15 pm – 11.30 am
M. Johannsen, S. Peper, M. Lübbert, Techn. Univ.
Hamburg-Harburg/Germany, The successful Use of
Simulated Moving Bed Chromatography with Supercritical
Fluids for the Separation of Enantiomers
11.30 am – 11.45 am
D. M.Wallworth, T. E. Beesley, Advanced Separation
Technologies/UK, Analytical and Preparative Chiral
Separations of Natural and Synthetic Amino Acids
11.45 am – 12.00
U. J. Meierhenrich, M.-J. Nguyen, B. Barbier, A. Brack, W.
H.-P. Thiemann, Bremen University/Germany and Centre de
Biophysique Moléculaire/France, Resolution of Saturated
Aliphatic Hydrocarbon Enantiomers on permethylated βCyclodextrin
Session 15
Chiroptical Phenomena II
Chair: N. Berova, M. Hollosi
10.45 am – 11.00 am
E. Butkus, J. Malinauskiene, E. Orentas, S. Stoncius, A.
Pilinskas, Vilnius University/Lithuania, Chromophore
Interaction in Chiral Bicyclic Structures evidenced by
Circular Dichroism Spectroscopy
11.00 am – 11.15 am
P.L. Polavarapu, F. Wang, Vanderbilt University/USA,
Techniques for Determination of Absolute Configurations
and Predominant Conformations of chiral Molecules in
Solution Phase
11.15 pm – 11.30 am
J. Frelek, R. Lysek, K. Borsuk, A. Klimek, M. Chmielewski,
Polish Academy of Sciences/Poland, Chiroptical Properties
of polycyclic β-Lactam Derivatives
11.30 am – 11.45 am
L.A. Nafie, R. K. Dukor, T. B. Freedman, X. Cao, C. Guo,
D. A. Dunmire, R. Shah, Syracuse University, BioTools, R.
W. Johnson Pharmac. Res./USA, Vibrational Chirality:
Absolute Configuration, Conformational Analysis and
Enantiomeric Excess Monitoring with VCD
19
14th International Symposium on Chirality
11.45 am – 12.00
K. Nakanishi, Y. Fujomoto, N. Fishkin, G. Pescitteli, J.
Decatur, N. Berova, Columbia University/USA, Mode of
Entry of 11-cis-Retinal into Rhodopsin and its Conformation
in the Pigment
12.00
J. Gawronski, Adam Mickiewicz
University/Poland, Novel Concept Chromophores: Absolute
Configuration and Conformation by Circular Dichroism
Spectroscopy
- 12.15 pm
12.15 pm – 1.30 pm
Lunch Break
Plenary Session 16 Relevance of Chirality in Environmental Analysis
Chair: H. Aboul-Enein, W. A. König.
1.30 pm – 2.00 pm
H. Hühnerfuss, S. Biselli, S. During, R. Gatermann, M.
Hecker, R. Kallenborn, L. Karbe, W. A. König, G. G.
Rimkus, University of Hamburg/Germany, Biotic and
Abiotic Transformation of polycyclic Musks studied by
Enantioselective Chromatographic Analyses
2.00 pm – 2.30 pm
R. Kallenborn, U. Berger, A. Götsch, W. Vetter, Norwegian
Institute of Air Res./Norway and University of
Jena/Germany, Congener- and Enantiomer selective Liquid
Chromatographic
Separation
of
Atropisomeric
polybrominated Biphenyls(PBB)
2.30 pm – 3.00 pm
Coffee Break
Plenary Session 17
General Aspects in the Analysis of chiral Molecules
Chair: J. Gal, K. Saigo
3.00 pm – 3.30 pm
G. W. Yanik, PDR-Chiral/USA, Determining "ee" to high
Precision (0.1%) in Pharmaceuticals using UV, Polarimetry
and Deconvolution Software
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14th International Symposium on Chirality
3.30 pm – 4.00 pm
I. M. Mutton, P. J. Borman, R. J. Boughflower, K. W.
Freebairn, G. D. Jonas, A. Patel, M. T. Sanders, D.
Thompson,
Strategic
Technologies
and
CASS
GlaxoSmithKline/UK, Comparative Performances of HPLC,
CE and SFC with a chemically Diverse Sample Set
4.00 pm
Invitation to ISCD 15, 2003
4.15 pm
Closure of ISCD 14
21