Reviewing mobile phases used on Chiralcel OD through an application of data mining tools to CHIRBASE database

During the past decade, thousands of compounds have been resolved on Chiral cel OD (a cellulose-based chiral stationary phase) under diverse eluting co nditions. Many researches have documented the effects of mobile phase on en antioselectivity for a given family of samples but today no comprehensive s tudy aimed at identifying the-associations between the structural features present on solute and appropriate mobile phase conditions has yet been prop osed. In this review of mobile phases used on Chiralcel OD, we try to go fa r beyond a simple enumeration of eluting conditions and an effort is made t o explore the utility of data mining tools for assessing the knowledge cont ained in CHIRBASE database. We have extracted from CHIRBASE the chemical fe atures of 2363 chiral compounds separated on Chiralcel OD and their corresp onding mobile phases. This data set was submitted to data mining programs f or molecular pattern recognition and mobile phase predictions for new cases . Some substructural characteristics of solutes were related to the efficie nt use of some specific mobile phases. For example, the application of CH3C N/salt buffer at pH 6-7 was found convenient for reversed-phase separation of compounds bearing a tertiary amine functional group. Futhermore, a clust er analysis allowed the arrangement of the mobile phases according to simil arity found in molecular patterns of solutes. A decision tree, which may le ad to a more rational choice of the mobile phase under reversed-phase condi tions, is also proposed. (C) 2001 Elsevier Science B.V.All rights reserved.