Enantioseparation of phenylglycinol in chiral-modified zeolite HY: a molecular simulation study.
A mechanism has been proposed for the separation of valinol enantiomers using a chiral-modified zeolite HY (i.e., zeolite HY containing (+)-(1R;2R)-hydrobenzoin) Molecular modeling of chiral-modified zeolite HY employed in enantioselective separation. Jirapongphan SS, Warzywoda J, Budil DE, Sacco A Jr. Chirality 2007; in press, which accurately predicted the experimentally measured enantioseparation. This methodology has been applied to predict the separation of an enantiomeric pair of phenylglycinol molecules (a precursor in the synthesis of HIV-1 protease inhibitors) using the modified zeolite HY as a CSP. Phenylglycinol and valinol molecules are similar in terms of the presence of polar (i.e., amine and hydroxyl) groups. These functional groups are important in the proposed chiral discrimination. Supercage-based docking simulations yielded an enantioselectivity of 1.3 with (+)-(S)-phenylglycinol molecule better retained in the zeolite. Also, the simulations predicted two binding modes that were the same as those in the valinol system. This suggests that specific structural features (i.e., number and type of polar groups), which generate the hypothesized binding modes, are required in an enantioseparation utilizing the chiral-modified zeolite HY.
Jirapongphan
Siricharn S
SS
Department of Chemical Engineering, Center for Advanced Microgravity Materials Processing, Northeastern University, Boston, Massachusetts 02115, USA.
Warzywoda
Juliusz
J
Budil
David E
DE
Sacco
Albert
A
D001573:Benzoin / Q000737:chemistry; D003198:Computer Simulation; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D012984:Software; D013237:Stereoisomerism; D013816:Thermodynamics; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry; D017641:Zeolites / Q000737:chemistry*
D004983:Ethanolamines; D017641:Zeolites; C040994:valinol; C005332:N-phenylethanolamine; D014633:Valine; D001573:Benzoin; D005998:Glycine