JOURNAL 819


Organic Communications
VOLUME & ISSUE
Year: 2017 Issue: 3 July-September
PAGES
p.216 - 227
STATISTICS
Viewed 2140 times.
AUTHORS
    Reşit Çakmak, Selami Ercan, Murat Sünkür, Hayrullah Yılmaz and Giray Topal
PDF OF ARTICLE

GRAPHICAL ABSTRACT


ABSTRACT


This study consists of two parts. In the first part of the study; a Pirkle-type chiral stationary phase was prepared by synthesizing an aromatic amine derivative of (R)-2-amino-1-butanol as a chiral selectorand binding to L- tyrosine -modified cyanogen bromide (CNBr)-activated Sepharose 4B and then, packed into the separation column. T he chromatographic performance of the separation column was evaluated w ith racemic mandelic acid and 2-phenylpropionic acid by using phosphate buffers at three different pHs as mobile phase. In the resolution processes, t he prepared solutions were loaded onto the separation column at two different concentrations and at three different pHs for each racemic organic acid, separately. Enantiomeric excess (ee % ) of the eluates was determined on CHIRALPAK AD-H chiral analytical column by HPLC. The maximum ee% for mandelic acid and 2-phenylpropionic acid was determined to be 60.84 and 27.4, respectively. Separation factors (k 1 ’, k 2 ’, α, and Rs) were calculated for each acid. The structures of the obtained compounds were characterized using the spectroscopic methods (NMR, and elemental analysis). In the second part of the study; enantioselective interactions between the prepared CSP and the analytes have been widely studied by docking, molecular dynamics simulation and quantum mechanical computation methods. The reason of column eluation of rac-2-phenylpropionic acid with lower enantiomeric yield was explained by these techniques.

KEYWORDS
  • Pirkle-type chiral stationary phase
  • enantioseparation
  • molecular dynamics
  • docking

SUPPORTING INFORMATION


Supporting Information
Download File 26-OC-1707-037-SI.pdf (676.91 KB)