Jump to main content
Jump to site search
Publishing
Advanced

Issue 1, 2011
Previous Article Next Article

Separation of enantiomers on diastereomeric right- and left-handed helical poly(phenyl isocyanide)s bearing L-alanine pendants immobilized on silica gel by HPLC

Kazumi Tamura,a  Toshitaka Miyabe,a  Hiroki Iidaa  and  Eiji Yashima*a 
Author affiliations

* Corresponding authors

a Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Japan
E-mail: yashima@apchem.nagoya-u.ac.jp
Fax: +81-52-789-3185
Tel: +81-52-789-4495

Abstract

Diastereomeric left- and right-handed helical polyisocyanides composed of L-alanine-bound phenyl isocyanides were prepared. The helical polymers with a narrow molecular weight distribution were immobilized on a silica gel support via chemical bonding and their optical resolution abilities were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). The CSP prepared from the left-handed helical polyisocyanide resolved racemic cyclic ether and carbonyl compounds and cyclic dianilides and dibenzamides, whereas the right-handed helical polyisocyanide-based CSP showed a rather complementary chiral recognition ability and specifically resolved racemic metal acetylacetonate complexes, which were not separated on the former CSP at all. Additionally, the elution order of some enantiomers was reversed on the CSPs, thus indicating that the macromolecular helicity of the L-alanine-bound-polyisocyanides played a critical role in the enantioselectivity and elution order of the enantiomers.

Graphical abstract: Separation of enantiomers on diastereomeric right- and left-handed helical poly(phenyl isocyanide)s bearing l-alanine pendants immobilized on silica gel by HPLC

Back to tab navigation
Download options Please wait...

Publication details

The article was received on 24 May 2010, accepted on 26 Jul 2010 and first published on 23 Aug 2010


Article type: Paper
DOI: 10.1039/C0PY00164C
Citation: Polym. Chem., 2011,2, 91-98
  •   Request permissions

    Separation of enantiomers on diastereomeric right- and left-handed helical poly(phenyl isocyanide)s bearing L-alanine pendants immobilized on silica gel by HPLC

    K. Tamura, T. Miyabe, H. Iida and E. Yashima, Polym. Chem., 2011, 2, 91
    DOI: 10.1039/C0PY00164C

    If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using Copyright Clearance Center. Go to our Instructions for using Copyright Clearance Center page for details.

    Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.
    • For reproduction of material from PCCP:
      Reproduced from Ref. XX with permission from the PCCP Owner Societies.
    • For reproduction of material from PPS:
      Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.
    • For reproduction of material from all other RSC journals and books:
      Reproduced from Ref. XX with permission from The Royal Society of Chemistry.

    If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

    In all cases the Ref. XX is the XXth reference in the list of references.

    If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC
    • For reproduction of material from PCCP:
      [Original citation] - Reproduced by permission of the PCCP Owner Societies
    • For reproduction of material from PPS:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
    • For reproduction of material from all other RSC journals:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry

    If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements