Prime

Type your tag names separated by a space and hit enter

Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds.

Abstract

Eight diproline chiral stationary phases with different end-capping groups were prepared and evaluated for the enantio-selective resolution of 41 racemic analytes. The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased significantly without it. In general, increasing steric bulkiness near the N-terminal of diproline increases the enantioselectivity. Electronic structures of the end-capping groups are also important. One stationary phase with an adamantanecarbonyl capping group was found to provide both higher average separation and resolution factors than our previous leader. Three other stationary phases with 2-methylpropanoyl, cyclopropanecarbonyl and cyclobutanecarbonyl end capping groups were found to provide comparable average separation factor but higher resolution factors than our previous leader.

Links

  • PMC Free PDF
  • PMC Free Full Text
  • Publisher Full Text
  • Authors

    , , ,

    Source

    Journal of chromatography. A 1218:32 2011 Aug 12 pg 5498-503

    MeSH

    Adsorption
    Chromatography, High Pressure Liquid
    Organic Chemicals
    Proline
    Stereoisomerism

    Pub Type(s)

    Journal Article
    Research Support, N.I.H., Extramural

    Language

    eng

    PubMed ID

    21741656