Modeling the chromatographic enantioseparation of Aryl- and hetarylcarbinols on ULMO, a brush-type chiral stationary phase, by 3D-QSAR techniques

Chirality

Volumn 15, Issue 3, 2003, Pages 271-275

  Fabian, Walter M F ^a   Stampfer, Wolfgang ^a   Mazur, Monika ^b   Uray, Georg ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b JAN KOCHANOWSKI UNIVERSITY   (Poland)

Author keywords

Arylalcohols; CoMFA; Comparative molecular field analysis; Comparative molecular similarity indices analysis; CoMSIA; Enantioselectivity; EVA descriptor; MOPAC calculation; Separation factor

Indexed keywords

ALCOHOL DERIVATIVE; METHANOL DERIVATIVE;

ARTICLE; CALCULATION; CHIRALITY; CHROMATOGRAPHY; ENANTIOSELECTIVITY; MODEL; PRIORITY JOURNAL; PURIFICATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 0037285348     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10197     Document Type: Article

References (30)

1. Maier NM, Uray G. Diphenylethanediamine (DPEDA) derivatives as chiral selectors. V. Efficient normal-phase high-performance liquid chromatographic enantioseparation of underivatized chiral arylalcohols on four differently linked 3,5-dinitrobenzoyldiphenylethanediamine-derived chiral stationary phases. J Chromatogr A 1996;732: 215-230.
2. Uray G, Niederreiter KS, Maier NM, Spitaler MM. Diphenylethanediamine (DPEDA) as chiral selector. IX. Self recognition of chiral selectors - efficient HPLC separation of the enantiomers of 3,5-dinitrobenzoylated diphenylalkaneamides on the immobilized analogue. Chirality 1999;11:404-408.
3. Cramer RD III, Patterson DE, Bunce JD. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 1988;110:5959-5967.
4. Marshall GR, Cramer RD III. Three-dimensional structure-activity relationships. Trends Pharmacol Sci 1988;9:285-289.
5. Kubinyi H. Comparative molecular field analysis (CoMFA). In: Schleyer PvR, editor. Encyclopedia of computational chemistry. Chichester, UK: John Wiley & Sons; 1998. p 448-460.
6. Kim KH, Greco G, Novellino E. A critical review of recent CoMFA applications. In: Kubinyi H, Folkers G, Martin YC, editors. 3D QSAR in drug design: recent advances. Leiden: KLUWER/ESCOM; 1998. Vol. 3, p 257-315.
7. Norinder U. Recent progress in CoMFA methodology and related techniques. Perspect Drug Discov Des 1998;12/13/14:25-39.
8. Suzuki T, Timofei S, Iuoras BE, Uray G, Verdino P, Fabian WMF. Quantitative structure-enantioselective retention relationships for chromatographic separation of arylalkylcarbinols on Pirkle type chiral stationary phases. J Chromatogr A 2001;922:13-23.
9. ULMO. www.registech.com/chiral
10. Schefzick S, Lämmerhofer M, Lindner W, Lipkowitz KB, Jalaie M. Comparative molecular field analysis of quinine derivatives used as chiral selectors in liquid chromatography: 3D QSAR for the purposes of molecular design of chiral stationary phases. Chirality 2000;12:742-750.
11. 2-1,2,4-oxadiazolines on R,R-DACH-DNB chiral stationary phase. Chirality 1996;8:556-566.
12. Carotti A, Altomare C, Cellamare S, Monforte A-M, Bettoni G, Loiodice F, Tangari N, Tortorella V. LFER and CoMFA studies on optical resolution of α-alkyl α-aryloxy acetic acid methyl esters on DACH-DNB chiral stationary phase. J Comput-Aid Mol Des 1995;9:131-138.
13. Altomare C, Carotti A, Cellamare S, Fanelli F, Gasparrini F, Villani C, Carrupt PA, Testa B. Enantiomeric resolution of sulfoxides on a DACH-DNB chiral stationary phase: a quantitative structureenantioselective retention relationship (QSERR) study. Chirality 1993; 5:527-537.
14. Klebe G. Comparative molecular similarity indices analysis. CoMSIA. Perspect Drug Discov Des 1998;12/13/14:87-104.
15. Kubinyi H, Hamprecht FA, Mietzner T. Three-dimensional quantitative similarity-activity relationships (3D QSiAR) from SEAL similarity matrices. J Med Chem 1998;41:2553-2564.
16. Klebe G, Abraham U, Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 1994;37:4130-4146.
17. Turner DB, Willett P. The EVA spectral descriptor. Eur J Med Chem 2000;35:367-375.
18. Turner DB, Willett P, Ferguson AM, Heritage TW. Evaluation of a novel molecular vibration-based descriptor (EVA) for QSAR studies. 2. Model validation using a benchmark steroid dataset. J Comput-Aid Mol Des 1999;13:271-296.
19. Heritage TW, Ferguson AM, Turner DB, Willett P. EVA. A novel theoretical descriptor for QSAR studies. Perspect Drug Discov Des 1998;9/ 10/11:381-398.
20. Turner DB, Willett P, Ferguson AM, Heritage T. Evaluation of a novel infrared range vibration-based descriptor (EVA) for QSAR studies. 1. General application. J Comput-Aid Mol Des 1997;11:409-422.
21. Ferguson AM, Heritage T, Jonathon P, Pack SE, Phillips L, Rogan J, Snaith PJ. EVA: a new theoretically based molecular descriptor for use in QSAR/QSPR analysis. J Comput-Aid Mol Des 1997;11:143-152.
22. Ginn CMR, Turner DB, Willett P, Ferguson AM, Heritage TW. Similarity searching in files of three-dimensional chemical structures: evaluation of the EVA descriptor and combination of rankings using data fusion. J Chem Inf Comput Sci 1997;37:23-37.
23. Sybyl 6.8, Tripos Inc., St. Louis, MO, USA.
24. Stewart JJP. MOPAC: a semiempirical molecular orbital program. J Comput-Aid Mol Des 1990;4:1-105.
25. Baker J. An algorithm for the location of transition states. J Comput Chem 1986;7:385-395.
26. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc 1985; 107:3902-3909.
27. Wold S, Dunn WJ, Ruhe A, Wold H. The collinearity problem in linearregression - the partial least-squares (PLS) approach to generalized inverses. Siam J Sci Stat Comput 1984;5:735-743.
28. Cramer RD, Bunce JD, Patterson DE, Frank IE. Cross-validation, bootstrapping, and partial least-squares compared with multiple-regression in conventional QSAR studies. Quant Struct-Act Relat 1988;7:18-25.
29. Burk MJ, Hems W, Herzberg D, Malan C, Zanotti-Gerosa A. A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones. Org Lett 2000;2:4173-4176.
30. Doucet H, Fernandez E, Layzell TP, Brown JM. The scope of catalytic asymmetric hydroboration/oxidation with rhodium complexes of 1,1′-(2-diarylphosphino-1-naphthyl)isoquinolines. Chem Eur J 1999;5:1320-1330.