A computational study of cation–π interactions in polycyclic systems: exploring the dependence on the curvature and electronic factors

Priyakumar, U. Deva; Punnagai, M.; Mohan, Gunjan; Sastry, G. Narahari

doi:10.1016/j.tet.2004.01.086

Cited by 90 publications

(57 citation statements)

References 64 publications

(10 reference statements)

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“…The molecule T3 has C 3 symmetry, the central connecting moiety is bowl-shaped. Its bowl depth (BD) is 1.532 Å which agrees with the experimental value 1.486 Å [26]. The C=C connected to the center is twisted about 19.6°and 4.3°from the adjacent surface of sumanene 3O and the peripheric phenyl plane, respectively.…”

Section: Geometry Optimization and Electronic Structuresupporting

confidence: 85%

A comparative study of the two-photon absorption properties of a new three-branched molecule—sumanene 3O derivative and relative molecules

et al. 2006

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Section: Geometry Optimization and Electronic Structuresupporting

confidence: 85%

A comparative study of the two-photon absorption properties of a new three-branched molecule—sumanene 3O derivative and relative molecules

et al. 2006

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“…The side chain imidazole of His is an aromatic ring. Histidine can take part in the cation-π interactions as the aromatic motif with metallic cations or organic cations (protonated amino acids, Lys + and Arg + ) [7,9-11]. On the other hand, the protonated His + is an organic cation, which can join the cation-π interactions as an organic cation with other aromatic amino acids (Phe, Tyr, and Trp) [12-16].…”

Section: Introductionmentioning

confidence: 99%

“…The unique behaviors of histidine have been discussed in literatures from different aspects [7,32]. However, the quantitative interaction energies of five interaction types and the factors affecting the interaction energies still need more investigations.…”

Section: Introductionmentioning

confidence: 99%

The multiple roles of histidine in protein interactions

Liao

et al. 2013

Chemistry Central Journal

380

282

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BackgroundAmong the 20 natural amino acids histidine is the most active and versatile member that plays the multiple roles in protein interactions, often the key residue in enzyme catalytic reactions. A theoretical and comprehensive study on the structural features and interaction properties of histidine is certainly helpful.ResultsFour interaction types of histidine are quantitatively calculated, including: (1) Cation-π interactions, in which the histidine acts as the aromatic π-motif in neutral form (His), or plays the cation role in protonated form (His+); (2) π-π stacking interactions between histidine and other aromatic amino acids; (3) Hydrogen-π interactions between histidine and other aromatic amino acids; (4) Coordinate interactions between histidine and metallic cations. The energies of π-π stacking interactions and hydrogen-π interactions are calculated using CCSD/6-31+G(d,p). The energies of cation-π interactions and coordinate interactions are calculated using B3LYP/6-31+G(d,p) method and adjusted by empirical method for dispersion energy. ConclusionsThe coordinate interactions between histidine and metallic cations are the strongest one acting in broad range, followed by the cation-π, hydrogen-π, and π-π stacking interactions. When the histidine is in neutral form, the cation-π interactions are attractive; when it is protonated (His+), the interactions turn to repulsive. The two protonation forms (and pKa values) of histidine are reversibly switched by the attractive and repulsive cation-π interactions. In proteins the π-π stacking interaction between neutral histidine and aromatic amino acids (Phe, Tyr, Trp) are in the range from -3.0 to -4.0 kcal/mol, significantly larger than the van der Waals energies.

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“…Understandably, the binding energy of metal complexes decreases with increase in the size of the metal ion, in accordance with earlier results. 16,21 Placement of the metal ions at the centroid of the dehydroannulenes did not lead to stationary points …”

Section: Resultsmentioning

confidence: 97%

Metal ion binding with dehydroannulenes — Plausible two-dimensional molecular sieves

2007

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A computational study of cation–π interactions in polycyclic systems: exploring the dependence on the curvature and electronic factors

Cited by 90 publications

References 64 publications

A comparative study of the two-photon absorption properties of a new three-branched molecule—sumanene 3O derivative and relative molecules

A comparative study of the two-photon absorption properties of a new three-branched molecule—sumanene 3O derivative and relative molecules

The multiple roles of histidine in protein interactions

Metal ion binding with dehydroannulenes — Plausible two-dimensional molecular sieves

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