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Enantioseparation of phenylglycinol in chiral‐modified zeolite HY: A molecular simulation study
Author(s) -
Jirapongphan Siricharn S.,
Warzywoda Juliusz,
Budil David E.,
Sacco Albert
Publication year - 2007
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20407
Subject(s) - chemistry , chirality (physics) , zeolite , enantiomer , enantioselective synthesis , molecule , amine gas treating , computational chemistry , molecular dynamics , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , physics , chiral symmetry breaking , nambu–jona lasinio model , quark , quantum mechanics
A mechanism has been proposed for the separation of valinol enantiomers using a chiral‐modified zeolite HY (i.e., zeolite HY containing (+)‐(1 R ;2 R )‐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. Chirality, 2007. © 2007 Wiley‐Liss, Inc.