Exploring enantioselective molecular recognition mechanisms with chemoinformatic techniques

被引:47
作者
Del Rio, Alberto [1 ]
机构
[1] Univ Modena & Reggio Emilia, Dipartimento Sci Farmaceut, I-41100 Modena, Italy
关键词
Chemoinformatics; Chiral discrimination; Chirality descriptors; Chiral separation; CoMFA; Computational chemistry; CoMSIA; Data mining; Enantioselective chromatography; Enantioselective recognition mechanisms; LFER; LSER; QSER; QSERR; QSRR; CHIRAL STATIONARY-PHASE; PERFORMANCE LIQUID-CHROMATOGRAPHY; HUMAN SERUM-ALBUMIN; SOLVATION ENERGY RELATIONSHIPS; STRUCTURE-RETENTION RELATIONSHIPS; MOVING-BED CHROMATOGRAPHY; DATA MINING TOOLS; QUANTITATIVE STRUCTURE; FIELD ANALYSIS; VARIABLE SELECTION;
D O I
10.1002/jssc.200800693
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
A comprehensive review of chemoinformatic techniques and studies applied to the field of enantioselective molecular recognition is presented. Several approaches such as enantiophores/pharmacophore modelling, QSPRs, CoMFA and other insightful data mining procedures are discussed. The review focuses on the central role of chemoinformatic approaches on the establishment of connections between available experimental data, mainly HPLC separation data, and these algorithms that describe properties of chiral molecules. The general overview of the aforementioned calculations account for a use of these techniques as a valuable strategy to achieve reliable prediction systems, infer the mechanisms of chiral recognition, generate insight for the conception of new chiral receptors and corroborate and assist experimental techniques such as chiral LC. Moreover, it is pointed out that computer methods in this field promise a wide range of applications for both academia and industry, ranging from enantioselective reactions, drug discovery and analysis of high-throughput screenings, to analytical and semi-preparative separations or large-scale production of enantiopure compounds.
引用
收藏
页码:1566 / 1584
页数:19
相关论文
共 177 条
[71]   Analysis and optimization of structure-based virtual screening protocols (1): exploration of ligand conformational sampling techniques [J].
Good, AC ;
Cheney, DL .
JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2003, 22 (01) :23-30
[72]  
GUNER FO, 1999, PHARMACOPHORE PERCEP
[73]   Enantiomer Separation of Imidazo-Quinazoline-Dione Derivatives on Quinine Carbamate-Based Chiral Stationary Phase in Normal Phase Mode [J].
Gyimesi-Forras, Kristina ;
Maier, Norbert M. ;
Kokosi, Jozsef ;
Gergely, Andras ;
Lindner, Wolfgang .
CHIRALITY, 2009, 21 (01) :199-207
[74]   Quantitative structure-(chromatographic) retention relationships [J].
Heberger, Karoly .
JOURNAL OF CHROMATOGRAPHY A, 2007, 1158 (1-2) :273-305
[75]   Construction of 3D-QSAR models using the 4D-QSAR analysis formalism [J].
Hopfinger, AJ ;
Wang, S ;
Tokarski, JS ;
Jin, BQ ;
Albuquerque, M ;
Madhav, PJ ;
Duraiswami, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) :10509-10524
[76]   Retention and chiral recognition mechanism of organo-phosphorus compounds in high-performance liquid chromatography [J].
Huang, JM ;
Chen, H ;
Gao, RY ;
Wang, QS ;
Chen, RY .
SCIENCE IN CHINA SERIES B-CHEMISTRY, 2001, 44 (02) :147-153
[77]   Probability rule for chiral recognition [J].
Kafri, R ;
Lancet, D .
CHIRALITY, 2004, 16 (06) :369-378
[78]   Linear free energy relationship as a tool for characterization of three teicoplanin-based chiral stationary phases under various mobile phase compositions [J].
Kalikova, Kveta ;
Lokajova, Jana ;
Tesarova, Eva .
JOURNAL OF SEPARATION SCIENCE, 2006, 29 (10) :1476-1485
[79]   MECHANISM OF RETENTION OF BENZODIAZEPINES IN AFFINITY, REVERSED-PHASE AND ADSORPTION HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY IN VIEW OF QUANTITATIVE STRUCTURE-RETENTION RELATIONSHIPS [J].
KALISZAN, R ;
KALISZAN, A ;
NOCTOR, TAG ;
PURCELL, WP ;
WAINER, IW .
JOURNAL OF CHROMATOGRAPHY, 1992, 609 (1-2) :69-81
[80]   Retention data from affinity high-performance liquid chromatography in view of chemometrics [J].
Kaliszan, R .
JOURNAL OF CHROMATOGRAPHY B, 1998, 715 (01) :229-244