Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures

Salonen, Laura M.; Ellermann, Manuel; Diederich, François

doi:10.1002/anie.201007560

Cited by 1,356 publications

(1,103 citation statements)

References 688 publications

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“…Cysteine thiols that do not form disulfide bonds often contribute to protein structure stability by forming conventional hydrogen bonds. If the cysteine is in a hydrophobic environment, it is often engaged in electrostatic interactions with aromatic residues (73,74). The covalent addition of nitric oxide to the thiol group changes the geometry of the thiol-aromatic interaction.…”

Section: Discussionmentioning

confidence: 99%

Post-translational S-Nitrosylation Is an Endogenous Factor Fine Tuning the Properties of Human S100A1 Protein

Živković

Zaręba-Kozioł

Zhukova

et al. 2012

Journal of Biological Chemistry

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Background: S100A1 protein is a proposed target of molecule-guided therapy for heart failure. Results: S-Nitrosylation of S100A1 is present in cells, increases Ca 2ϩ binding, and tunes the overall protein conformation. Conclusion: Thiol-aromatic molecular switch is responsible for NO-related modification of S100A1 properties. Significance: Post-translational S-nitrosylation may provide functional diversity and specificity to S100A1 and other S100 protein family members.

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Section: Discussionmentioning

confidence: 99%

Post-translational S-Nitrosylation Is an Endogenous Factor Fine Tuning the Properties of Human S100A1 Protein

Živković

Zaręba-Kozioł

Zhukova

et al. 2012

Journal of Biological Chemistry

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“…Their striking manifestations include the properties of liquids, molecular recognition 4 or the structure and function of biomacromolecules, to name just a few 2,5 . In general, experiments make it possible to obtain information on the strength of noncovalent interactions e.g.…”

Section: Introductionmentioning

confidence: 99%

Quantum Monte Carlo for noncovalent interactions: an efficient protocol attaining benchmark accuracy

Dubecký

Derian

Jurečka

et al. 2014

Phys. Chem. Chem. Phys.

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Reliable theoretical predictions of noncovalent interaction energies, which are important e.g. in drug-design and hydrogenstorage applications, belong to longstanding challenges of contemporary quantum chemistry. In this respect, the fixed-node diffusion Monte Carlo (FN-DMC) is a promising alternative to the commonly used "gold standard" coupled-cluster CCSD(T)/CBS method for its benchmark accuracy and favourable scaling, in contrast to other correlated wave function approaches. This work is focused on the analysis of protocols and possible tradeoffs for FN-DMC estimations of noncovalent interaction energies and proposes an efficient yet accurate computational protocol using simplified explicit correlation terms with a favorable O(N 3 ) scaling. It achieves an excellent agreement (mean unsigned error ∼0.2 kcal/mol) with respect to the CCSD(T)/CBS data on a number of complexes, including benzene/hydrogen, T-shape benzene dimer, stacked adenine-thymine and a set of small noncovalent complexes A24. The high accuracy and reduced computational costs predestinate the reported protocol for practical interaction energy calculations of large noncovalent complexes, where the CCSD(T)/CBS is prohibitively expensive.

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“…Of high interest are noncovalent host-guest interactions which are mainly dominated by London forces [1][2][3][4][5][6] . The latter are considered as weak molecular interactions and increase with the size of the interacting moieties.…”

mentioning

confidence: 99%

Strongly underestimated dispersion energy in cryptophanes and their complexes

2014

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Cryptophanes, composed of two bowl-shaped cyclotriveratrylene subunits linked by three aliphatic linker groups, are prototypal organic host molecules which bind reversibly neutral small guest compounds via London forces. The binding constants for these complexes are usually measured in tetrachloroethane and are in the range of 10 2 -10 3 M À 1 . Here we show that tetrachloroethane is-in contrast to the scientific consensus-enclosed by the cryptophane-E cavity. By means of NMR spectroscopy we show that the binding constant for CHCl 3 @cryptophane-E is in larger solvents two orders of magnitudes higher than the one measured before. Ab initio calculations reveal that attractive dispersion energy is responsible for high binding constants and for the formation of imploded cryptophanes which seem to be more stable than cryptophanes with empty cavities.

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Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures

Cited by 1,356 publications

References 688 publications

Post-translational S-Nitrosylation Is an Endogenous Factor Fine Tuning the Properties of Human S100A1 Protein

Post-translational S-Nitrosylation Is an Endogenous Factor Fine Tuning the Properties of Human S100A1 Protein

Quantum Monte Carlo for noncovalent interactions: an efficient protocol attaining benchmark accuracy

Strongly underestimated dispersion energy in cryptophanes and their complexes

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