The nature of cation-pi binding: interactions between tetramethylammonium ion and benzene in aqueous solution

Gao, Jiali; Chou, Li-Hsien; Auerbach, Anthony

doi:10.1016/s0006-3495(93)81031-2

Cited by 55 publications

(36 citation statements)

References 25 publications

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“…Quaternary ammonium compounds also exhibit a preference for aromatic rings (Gao et al, 1993;Ripoll et al, 1993). The occurrence of aromatic phenyl interactions with the R-N+(CH3)3 group has also been noted in crystal structures of small molecules from the Cambridge Structural Database (Verdonk et al, 1993).…”

Section: Charge Interactionsmentioning

confidence: 83%

“…I I Mrabet et al (1992) showed that Lys -+ Arg mutations in thermostable xylose isomerase (IX) from Actinoplanes missouriensis imparted a significant stability under increasing heat conditions. Quaternary ammonium compounds also exhibit a preference for aromatic rings (Gao et al, 1993;Ripoll et al, 1993). The occur-rence of aromatic phenyl interactions with the R-N+(CH3)3 group has also been noted in crystal structures of small molecules from the Cambridge Structural Database (Verdonk et al, 1993).…”

Section: Charge Interactionsmentioning

confidence: 83%

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A preference-based free-energy parameterization of enzyme-inhibitor binding. Applications to HIV-1-protease inhibitor design

1995

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The interface between protein receptor-ligand complexes has been studied with respect to their binary interatomic interactions. Crystal structure data have been used to catalogue surfaces buried by atoms from each member of a bound complex and determine a statistical preference for pairs of amino-acid atoms. A simple free energy model of the receptor-ligand system is constructed from these atom-atom preferences and used to assess the energetic importance of interfacial interactions. The free energy approximation of binding strength in this model has a reliability of about * 1.5 kcal/mol, despite limited knowledge of the unbound states. The main utility of such a scheme lies in the identification of important stabilizing atomic interactions across the receptor-ligand interface. Thus, apart from an overall hydrophobic attraction (Young L, Jernigan RL, Covell DG, 1994, Protein Sci3:717-729), a rich variety of specific interactions is observed. An analysis of 10 HIV-1 protease inhibitor complexes is presented that reveals a common binding motif comprised of energetically important contacts with a rather limited set of atoms. Design improvements to existing HIV-1 protease inhibitors are explored based on a detailed analysis of this binding motif.

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Section: Charge Interactionsmentioning

confidence: 83%

Section: Charge Interactionsmentioning

confidence: 83%

A preference-based free-energy parameterization of enzyme-inhibitor binding. Applications to HIV-1-protease inhibitor design

1995

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“…Ibuprofen and omeprazole have aromatic rings, ether, amine and carboxylic groups, responsible for various interactions with the PFP groups (Dougherty, 2007;Martinez & Iverson, 2012). The retention mechanism in reverse-phase chromatography involves various interactions such as π-π interactions, hydrogen bondings, hydrophobic interactions and electrostatic interactions (Aboul-Enein & Ali, 2001b;Gao, Chou, & Auerbach, 1993;Imai, Inoue, Nakanishi, & Kitaura, 2009;Mohan, Vijayalakshmi, Koga, & Suresh, 2010;Ottiger, Pfaffen, Leist, & Leutwyler, 2009;Scrutton & Raine, 1996). This order of elution is very important to predict the mechanism of the separation of these drugs on the reported stationary phase.…”

Section: Mechanism Of Separationmentioning

confidence: 99%

Supramolecular separation mechanism of pentafluorophenyl column using ibuprofen and omeprazole as markers: LC‐MS and simulation study

Hussain

Alajmi

Ali

2018

Biomedical Chromatography

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The pentafluorophenyl (PFP) column is emerging as a new advancement in separation science to analyze a wide range of analytes and, thus, its separation mechanism at supramolecular level is significant. We developed a mechanism for the separation of ibuprofen and omeprazole using different combinations (ranging from 50:50 to 60:40) of water-acetonitrile containing 0.1% formic acid as the mobile phase. The column used was Waters Acquity UPLC HSS PFP (75 × 2.1 mm, 1.8 μm). The reverse order of elution was observed in different combinations of the mobile phases. The docking study indicated hydrogen bonding between ibuprofen and PFP stationary phase (binding energy was -11.30 kJ/mol). Separation at PFP stationary phase is controlled by hydrogen bonding along with π-π interactions. This stationary phase may be used to analyze both aromatic and aliphatic analytes. The developed mechanism will be useful to separate various analytes by considering the possible interactions, leading to saving of energy, time and money. In addition, this work will be highly useful in preparative chromatography where separation is the major problem at a large scale. Moreover, the developed LC-MS-QTOF method may be used to analyze ibuprofen and omeprazole in an unknown sample owing to the low value of detection limits.

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“…[94] A free energy barrier of about 3 kcal mol −1 was predicted between the contact pair and the solvent-separated species. Importantly, it was found that TMA has a greater affinity for benzene than for chloride ions, with a binding constant of 0.8 M −1.…”

Section: Applicationsmentioning

confidence: 99%

“…Importantly, it was found that TMA has a greater affinity for benzene than for chloride ions, with a binding constant of 0.8 M −1. [94] …”

Section: Applicationsmentioning

confidence: 99%

QM/MM through the 1990s: The First Twenty Years of Method Development and Applications

Liu

Wang

Chen

et al. 2014

Israel Journal of Chemistry

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The 2013 Nobel Prize in Chemistry was awarded to the authors of the first two publications utilizing the concept of combined quantum mechanical and molecular mechanical (QM/MM) methods. In celebrating this great event in computational chemistry, we review the early development of combined QM/MM techniques and the associated events that took place through the mid-1990s. We also offer some prospects for the future development of quantum mechanical techniques for macromolecular systems.

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The nature of cation-pi binding: interactions between tetramethylammonium ion and benzene in aqueous solution

Cited by 55 publications

References 25 publications

A preference-based free-energy parameterization of enzyme-inhibitor binding. Applications to HIV-1-protease inhibitor design

A preference-based free-energy parameterization of enzyme-inhibitor binding. Applications to HIV-1-protease inhibitor design

Supramolecular separation mechanism of pentafluorophenyl column using ibuprofen and omeprazole as markers: LC‐MS and simulation study

QM/MM through the 1990s: The First Twenty Years of Method Development and Applications

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