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Hig-performance stationary phases for the separation of chiral compounds and carbohydrates by designed grafting of monosized polymer supports

Hig-performance stationary phases for the separation of chiral compounds and carbohydrates by designed grafting of monosized polymer supports

Michael Buchmeiser (ORCID: )
  • Grant DOI 10.55776/P12963
  • Funding program Principal Investigator Projects
  • Status ended
  • Start August 1, 1998
  • End September 30, 2001
  • Funding amount € 213,148
  • Project website

Disciplines

Chemistry (100%)

Keywords

    ROMP, ROMP-POLYMERS, HPLC, CARBOHYDRATES, CHIRAL COMPOUNDS, STATIONARY PHASES

Final report

The main objective of this project was the synthesis and evaluation of new high-performance materials for liquid chromatography for the separation of biologically and pharmacologically relevant compounds. For this purpose, new synthetic methods, i. e. new polymerization techniques have been applied. Based on preliminary experiments and data from a previous project, the necessary key-synthetic steps had soon been realized. These basically consist of particular polymerization techniques that allow the exact and highly reproducible attachment of functionalized polymer chains onto a carrier (support). These polymer chains themselves function as carriers for various functional groups (small moieties of molecules) that are necessary in order to achieve separation. Metathesis Polymerization was used throughout. Applying this conceptually and synthetically absolutely novel approach of transition metal-based synthesis, a large variety of new stationary phases for high-performance liquid chromatography (HPLC) have been synthesized. In terms if support, a large number of PS-DVB- or silica-based chiral stationary phases was realized. These were used for in the separation of enantiomers (separation of chiral compounds that are related to each other by a mirror plane). For these purposes, both amino acid- and cyclodextrin- based stationary phases were used. Based on the same concept, new stationary phases for anion-chromatography have been realized. In this context, materials have been synthesized for the first time that consist of poly(metallocenium)-cations. The corresponding materials have been used successfully in the anion exchange chromatography of oligonucleotides. (oligonucleotides are the building blocks of DNA). A breakthrough was achieved in the area of new sorbents for metal extraction. Thus, sorbents have been realized that may be used in an "on-line" extraction and quantification process of rare- earth elements from complex matrices such as rocks. These materials may also be used in the enrichment of trace amounts of radioactive lanthanides as well as in wastewater clean-up. Finally, the concept of transition metal-catalyzed synthesis was applied to a the generation of a new class of polymeric supports, usually referred to "monolithic media". Besides of generating a new matrix, the traditional problems of functionalization as well as reproducibility in the synthesis of these materials have been solved. "Monoliths" prepared by the new approach turned out to be excellent separation media in BioScience and for Genomics. Thus, proteins, DNA fragments as well as oligonucleotides may be separated on these media within seconds. The great potential of these materials and this chemistry, respectively, turned out to be that promising that these materials are now used in current projects as carriers (supports) for catalyst immobilization.

Research institution(s)
  • Universität Innsbruck - 100%
Project participants
  • Herwig Schottenberger, Universität Innsbruck , associated research partner
  • Christian Gottfried Huber, Universität des Saarlandes , associated research partner

Research Output

  • 1010 Citations
  • 16 Publications
Publications
  • 2006
    Title Metathesis Polymerization To and From Surfaces
    DOI 10.1007/12_067
    Type Book Chapter
    Author Buchmeiser M
    Publisher Springer Nature
    Pages 137-171
  • 2001
    Title Metathesis-Based Monoliths: Influence of Polymerization Conditions on the Separation of Biomolecules
    DOI 10.1021/ac010452+
    Type Journal Article
    Author Mayr B
    Journal Analytical Chemistry
    Pages 4071-4078
  • 2001
    Title Chiral ß-cyclodextrin-based polymer supports prepared via ring-opening metathesis graft-polymerization
    DOI 10.1016/s0021-9673(00)01008-6
    Type Journal Article
    Author Mayr B
    Journal Journal of Chromatography A
    Pages 47-56
  • 2001
    Title New synthetic ways for the preparation of high-performance liquid chromatography supports
    DOI 10.1016/s0021-9673(00)00129-1
    Type Journal Article
    Author Buchmeiser M
    Journal Journal of Chromatography A
    Pages 233-266
  • 2001
    Title Influences of surface chemistry on the separation behavior of stationary phases for reversed-phase and ion-exchange chromatography: a comparison of coated and grafted supports prepared by ring-opening metathesis polymerization
    DOI 10.1016/s0021-9673(00)01024-4
    Type Journal Article
    Author Mayr B
    Journal Journal of Chromatography A
    Pages 73-80
  • 2001
    Title Bis(pyrimidine)-based palladium catalysts: synthesis, X-ray structure and applications in Heck–, Suzuki–, Sonogashira–Hagihara couplings and amination reactions
    DOI 10.1016/s0022-328x(01)01083-x
    Type Journal Article
    Author Buchmeiser M
    Journal Journal of Organometallic Chemistry
    Pages 39-46
  • 2001
    Title Alkyne Metathesis Graft Polymerization: Synthesis of Poly(ferricinium)-Based Silica Supports for Anion-Exchange Chromatography of Oligonucleotides
    DOI 10.1021/ma0019858
    Type Journal Article
    Author Eder K
    Journal Macromolecules
    Pages 4334-4341
  • 2000
    Title A New Class of Continuous Polymer Supports Prepared by Ring-Opening Metathesis Polymerization: A Straightforward Route to Functionalized Monoliths
    DOI 10.1021/ma000322n
    Type Journal Article
    Author Sinner F
    Journal Macromolecules
    Pages 5777-5786
  • 2000
    Title 57Fe-Mössbauer spectroscopic study of monomeric and polymeric ferrocenyl- and octamethylferrocenyl-substituted ethynes
    DOI 10.1016/s0022-328x(00)00280-1
    Type Journal Article
    Author Schottenberger H
    Journal Journal of Organometallic Chemistry
    Pages 1-8
  • 1999
    Title ROMP-Based, Highly Hydrophilic Poly(7-oxanorborn-2-ene-5,6-dicarboxylic acid)-Coated Silica for Analytical and Preparative Scale High-Performance Ion Chromatography
    DOI 10.1021/cm980772i
    Type Journal Article
    Author Buchmeiser M
    Journal Chemistry of Materials
    Pages 1533-1540
  • 1999
    Title X-ray structural investigations and conformational particularities of ethyne-derived organometallics based on ferrocene and fluorene
    DOI 10.1016/s0022-328x(99)00167-9
    Type Journal Article
    Author Schottenberger H
    Journal Journal of Organometallic Chemistry
    Pages 301-309
  • 1999
    Title Ring-Opening Metathesis Polymerization for the Preparation of Surface-Grafted Polymer Supports
    DOI 10.1021/ma9913966
    Type Journal Article
    Author Buchmeiser M
    Journal Macromolecules
    Pages 32-39
  • 1999
    Title Poly(7-oxanorborn-2-ene-5,6-dicarboxylate)-coated silica prepared by ring-opening metathesis polymerization for the selective enrichment of radioactive lanthanides
    DOI 10.1016/s0021-9673(99)00399-4
    Type Journal Article
    Author Seeber G
    Journal Journal of Chromatography A
    Pages 193-202
  • 1998
    Title On-Line Cation Exchange for Suppression of Adduct Formation in Negative-Ion Electrospray Mass Spectrometry of Nucleic Acids
    DOI 10.1021/ac980791b
    Type Journal Article
    Author Huber C
    Journal Analytical Chemistry
    Pages 5288-5295

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