Literature DB >> 11959939

Substituent effects on cation-pi interactions: a quantitative study.

Christopher A Hunter1, Caroline M R Low, Carmen Rotger, Jeremy G Vinter, Cristiano Zonta.   

Abstract

A synthetic supramolecular complex has been adapted to quantify cation-pi interactions in chloroform by using chemical double-mutant cycles. The interaction of a pyridinium cation with the pi-face of an aromatic ring is found to be very sensitive to the pi-electron density. Electron-donating substituents lead to a strong attractive interaction (-8 kJ/mol(-1)), but electron-withdrawing groups lead to a repulsive interaction (+2 kJ/mol(-1)).

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Year:  2002        PMID： 11959939      PMCID： PMC122686          DOI： 10.1073/pnas.072647899

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  12 in total

1.  Synthetic receptors as models for alkali metal cation-pi binding sites in proteins.

Authors:  S L De Wall; E S Meadows; L J Barbour; G W Gokel
Journal:  Proc Natl Acad Sci U S A       Date:  2000-06-06       Impact factor: 11.205

2.  The Cationminus signpi Interaction.

Authors:  Jennifer C. Ma; Dennis A. Dougherty
Journal:  Chem Rev       Date:  1997-08-05       Impact factor: 60.622

3.  Substituent effects on edge-to-face aromatic interactions.

Authors:  Fiona J Carver; Christopher A Hunter; David J Livingstone; James F McCabe; Eileen M Seward
Journal:  Chemistry       Date:  2002-07-02       Impact factor: 5.236

4.  Cation-pi interactions in aromatics of biological and medicinal interest: electrostatic potential surfaces as a useful qualitative guide.

Authors:  S Mecozzi; A P West; D A Dougherty
Journal:  Proc Natl Acad Sci U S A       Date:  1996-10-01       Impact factor: 11.205

5.  A mechanism for ion selectivity in potassium channels: computational studies of cation-pi interactions.

Authors:  R A Kumpf; D A Dougherty
Journal:  Science       Date:  1993-09-24       Impact factor: 47.728

6.  Cation-pi interactions in structural biology.

Authors:  J P Gallivan; D A Dougherty
Journal:  Proc Natl Acad Sci U S A       Date:  1999-08-17       Impact factor: 11.205

7.  Contribution of cation-pi interactions to the stability of protein-DNA complexes.

Authors:  R Wintjens; J Liévin; M Rooman; E Buisine
Journal:  J Mol Biol       Date:  2000-09-15       Impact factor: 5.469

8.  A supramolecular system for quantifying aromatic stacking interactions.

Authors:  H Adams; C A Hunter; K R Lawson; J Perkins; S E Spey; C J Urch; J M Sanderson
Journal:  Chemistry       Date:  2001-11-19       Impact factor: 5.236

Review 9.  Cation-pi interactions in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp.

Authors:  D A Dougherty
Journal:  Science       Date:  1996-01-12       Impact factor: 47.728

10.  From ab initio quantum mechanics to molecular neurobiology: a cation-pi binding site in the nicotinic receptor.

Authors:  W Zhong; J P Gallivan; Y Zhang; L Li; H A Lester; D A Dougherty
Journal:  Proc Natl Acad Sci U S A       Date:  1998-10-13       Impact factor: 11.205
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  15 in total

Review 1.  Mutagenesis computer experiments in pentameric ligand-gated ion channels: the role of simulation tools with different resolution.

Authors:  Alessandro Crnjar; Federico Comitani; Claudio Melis; Carla Molteni
Journal:  Interface Focus       Date:  2019-04-19       Impact factor: 3.906

2.  Molecular dynamics of β-hairpin models of epigenetic recognition motifs.

Authors:  Xiange Zheng; Chuanjie Wu; Jay W Ponder; Garland R Marshall
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

3.  Genetically encoded fluorophenylalanines enable insights into the recognition of lysine trimethylation by an epigenetic reader.

Authors:  Yan-Jiun Lee; M J Schmidt; Jeffery M Tharp; Annemarie Weber; Amber L Koenig; Hong Zheng; Jianmin Gao; Marcey L Waters; Daniel Summerer; Wenshe R Liu
Journal:  Chem Commun (Camb)       Date:  2016-10-18       Impact factor: 6.222

4.  Limiting assumptions in molecular modeling: electrostatics.

Authors:  Garland R Marshall
Journal:  J Comput Aided Mol Des       Date:  2013-01-26       Impact factor: 3.686

5.  Probing the catalytic potential of the hamster arylamine N-acetyltransferase 2 catalytic triad by site-directed mutagenesis of the proximal conserved residue, Tyr190.

Authors:  Xin Zhou; Naixia Zhang; Li Liu; Kylie J Walters; Patrick E Hanna; Carston R Wagner
Journal:  FEBS J       Date:  2009-10-23       Impact factor: 5.542

6.  Substituent effects in cation/pi interactions and electrostatic potentials above the centers of substituted benzenes are due primarily to through-space effects of the substituents.

Authors:  Steven E Wheeler; K N Houk
Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419

7.  Recognition of trimethyllysine by a chromodomain is not driven by the hydrophobic effect.

Authors:  Robert M Hughes; Kimberly R Wiggins; Sepideh Khorasanizadeh; Marcey L Waters
Journal:  Proc Natl Acad Sci U S A       Date:  2007-06-20       Impact factor: 11.205

8.  Alkyltransferase-like protein (Atl1) distinguishes alkylated guanines for DNA repair using cation-π interactions.

Authors:  Oliver J Wilkinson; Vitaly Latypov; Julie L Tubbs; Christopher L Millington; Rihito Morita; Hannah Blackburn; Andrew Marriott; Gail McGown; Mary Thorncroft; Amanda J Watson; Bernard A Connolly; Jane A Grasby; Ryoji Masui; Christopher A Hunter; John A Tainer; Geoffrey P Margison; David M Williams
Journal:  Proc Natl Acad Sci U S A       Date:  2012-10-29       Impact factor: 11.205

Review 9.  The use of hammett constants to understand the non-covalent binding of aromatics.

Authors:  Michael Lewis; Christina Bagwill; Laura K E Hardebeck; Selina Wireduaah
Journal:  Comput Struct Biotechnol J       Date:  2012-03-06       Impact factor: 7.271

10.  Substituent effects in hydrogen bonding: DFT and QTAIM studies on acids and carboxylates complexes with formamide.

Authors:  Borys Ośmiałowski
Journal:  J Mol Model       Date:  2014-07-15       Impact factor: 1.810
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