Document Detail


Enantioseparation of phenylglycinol in chiral-modified zeolite HY: a molecular simulation study.
MedLine Citation:
PMID:  17437262     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Siricharn S Jirapongphan; Juliusz Warzywoda; David E Budil; Albert Sacco
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Chirality     Volume:  19     ISSN:  0899-0042     ISO Abbreviation:  Chirality     Publication Date:  2007 Jun 
Date Detail:
Created Date:  2007-04-30     Completed Date:  2007-09-05     Revised Date:  2013-06-04    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  United States    
Other Details:
Languages:  eng     Pagination:  514-7     Citation Subset:  IM    
Affiliation:
Department of Chemical Engineering, Center for Advanced Microgravity Materials Processing, Northeastern University, Boston, Massachusetts 02115, USA.
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MeSH Terms
Descriptor/Qualifier:
Benzoin / chemistry
Computer Simulation
Glycine / analogs & derivatives*,  chemistry
Molecular Conformation
Software
Stereoisomerism
Thermodynamics
Valine / analogs & derivatives*,  chemistry
Zeolites / chemistry*
Chemical
Reg. No./Substance:
119-53-9/Benzoin; 1318-02-1/Zeolites; 473-75-6/valinol; 56-40-6/Glycine; 630DL2N96B/N-phenylethanolamine; 7004-03-7/Valine

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