Molecular modeling of chiral-modified zeolite HY employed in enantioselective separation

Siricharn S. Jirapongphan, Juliusz Warzywoda, David E. Budil, Albert Sacco

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Insight into enantioselective separation utilizing chiral-modified zeolite HY could be useful in designing a chiral stationary phase for resolving pharmaceutical compounds. A model was employed to better understand the enantioseparation of valinol in zeolite HY that contains (+)-(1R;2R)- hydrobenzoin as a chiral modifier. This model incorporates the zeolite support and accounts for the flexible change. Results from grand canonical Monte Carlo and molecular dynamics simulations indicate that the associated diastereomeric complex consists of a single (+)-(1R;2R)-hydrobenzoin and a single valinol molecules located in the zeolite HY supercage. Supercage-based docking simulation predicted an enantioselectivity of 2.6 compared with that of 1.4 measured experimentally. Also, the supercage-based docking simulation demonstrated a single binding motif in the S complex, and two binding motifs in the R complex. The multiple binding modes in the R complex resulted in its lower stability. This is hypothesized to be the origin of the weaker binding between (-)-(R)-valinol and the chiral modifier, and explains why (+)-(R)-valinol is retained more in the chiral-modified zeolite system studied.

Original languageEnglish
Pages (from-to)508-513
Number of pages6
JournalChirality
Volume19
Issue number6
DOIs
StatePublished - 2007

Keywords

  • Chiral discrimination
  • Chiral stationary phase
  • Enantioseparation
  • GCMC simulation
  • Molecular dynamics
  • Supercage-based docking
  • Zeolite HY

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