Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans Article

Sun, P, Wang, C, Breitbach, ZS et al. (2009). Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans . 81(24), 10215-10226. 10.1021/ac902257a



cited authors

  • Sun, P; Wang, C; Breitbach, ZS; Zhang, Y; Armstrong, DW

fiu authors

abstract

  • An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic-and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromaticfunctionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high "loadability" and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents. © 2009 American Chemical Society.

publication date

  • December 15, 2009

Digital Object Identifier (DOI)

start page

  • 10215

end page

  • 10226

volume

  • 81

issue

  • 24