Enantiophore modeling in 3D-QSAR. A data mining application on Whelk-O1 chiral stationary phase

Chirality
Alberto Del RioC Roussel

Abstract

A combination of the enantiophore concept described in a previous study and a quantitative structure enantioselective relationship (QSER) based on partial least squares (PLS) analysis is presented. In the present study, a comprehensive approach for describing the enantioselective binding properties of the Whelk-O1 chiral HPLC receptor is achieved using molecular descriptors calculated by the GRID program. The GRID descriptors allow us to describe the molecules in terms of their ability to form favorable interactions with independent chemical groups (probes) that can be related to receptor sites. For each molecule, we compute 120 enantiophore descriptors representing the energy contributions from all possible pairwise combinations of probes. The overall procedure was simplified by considering only the most energetically favorable locations and converting selected grid-point energies into alignment-independent descriptors. By using a training set of 143 diverse chiral compounds, an optimal PLS model requiring seven components was chosen by using the cross-validation method resulting in a correlation coefficient R2= 0.88 and a cross validated correlation coefficient Q2= 0.85. An interpretation of the model is proposed based upon a...Continue Reading

References

Oct 23, 1998·Journal of Molecular Graphics & Modelling·J V de Julián-OrtizJ Gálvez
Aug 24, 2000·Accounts of Chemical Research·K B Lipkowitz
Aug 24, 2000·Journal of Medicinal Chemistry·M A KastenholzT Fox
Oct 6, 2000·Journal of Medicinal Chemistry·R BenigniM R Varì
Feb 24, 2001·Journal of Chromatography. a·K B Lipkowitz
May 22, 2002·Protein Science : a Publication of the Protein Society·Vidyasankar Sundaresan, Ravinder Abrol
Jan 28, 2003·Journal of Chemical Information and Computer Sciences·Alexander Golbraikh, Alexander Tropsha
May 28, 2003·Journal of Chemical Information and Computer Sciences·Simona Funar-TimofeiWalter M F Fabian
Aug 21, 2003·Journal of Computer-aided Molecular Design·Joachim PaierWalter M F Fabian
Sep 19, 2003·Journal of Computer-aided Molecular Design·Alexander GolbraikhAlexander Tropsha
Jun 25, 2004·Journal of Chromatography. a·Christian RousselNicolas Vanthuyne

❮ Previous
Next ❯

Citations

May 27, 2014·Journal of Chromatography. a·Adrian Sievers-EnglerMichael Lämmerhofer
Apr 17, 2007·Journal of Chromatography. a·Chunfeng Zhao, N M Cann
Oct 1, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Robert P SheridanChristopher J Welch

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.