Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies
Yükleniyor...
Dosyalar
Tarih
2017-11
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
ACG Publications
Erişim Hakkı
info:eu-repo/semantics/openAccess
Attribution-ShareAlike 3.0 United States
Attribution-ShareAlike 3.0 United States
Özet
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 selector and binding to
L-tyrosine-modified cyanogen bromide (CNBr)-activated Sepharose 4B and then, packed into the separation
column. The chromatographic performance of the separation column was evaluated with racemic mandelic acid and
2-phenylpropionic acid by using phosphate buffers at three different pHs as mobile phase. In the resolution
processes, the 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 (k1
’
, k2
’
, 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.
Açıklama
Anahtar Kelimeler
Pirkle-Type Chiral Stationary Phase, Enantioseparation, Molecular Dynamics, Docking
Kaynak
WoS Q Değeri
N/A
Scopus Q Değeri
Q4
Cilt
10
Sayı
3
Künye
Çakmak, R., Ercan, S., Sünkür, M., Yılmaz, H., Topal, G. (2017). Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies. Organic Communications, 10 (3), pp. 216-227. https://dx.doi.org/10.25135/acg.oc.25.17.07.037
