pub145523 Article

cited authors

  • Wang, C; Armstrong, DW; Risley, DS

fiu authors

abstract

  • Boromycin is a macrodiolide that exists as a hydrophobic Böeseken complex formed from boric acid and a chiral polyhydroxy macrocyclic ligand. It was covalently bonded to silica gel through a urea linkage to an attached D-valine ester. When evaluated as a chiral stationary phase, it shows pronounced enantioselectivity toward primary amine-containing racemates, separating 98% of those tested. The selectivity is most pronounced in the presence of organic solvents and supercritical CO2 + methanol. The enantioselective binding site and mechanistic factors are examined. Analytes can be complexed as either the free base or their protonated analogues, with the free base being more strongly associated with the chiral selector. © 2007 American Chemical Society.

Digital Object Identifier (DOI)

end page

  • 8135

volume

  • 79

issue

  • 21