Sulfur–Oxygen Chalcogen Bonding Mediates AdoMet Recognition in the Lysine Methyltransferase SET7/9

Fick, Robert J.; Kroner, Grace; Nepal, Binod; Magnani, Roberta; Horowitz, Scott; Houtz, Robert L.; Scheiner, Steve; Trievel, Raymond C.

doi:10.1021/acschembio.5b00852

Cited by 95 publications

(101 citation statements)

References 34 publications

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“…Moreover, the potential extendibility of the S⋅⋅⋅O ChB synthon motif beyond small molecule crystals into biological structures is substantiated by a recent report by Trievel et al., which shows the role of S⋅⋅⋅O ChB in mediating the S‐adenosylmethionine (AdoMet) recognition in the methyltransferase active site …”

Section: Resultsmentioning

confidence: 89%

Non‐Classical Synthons: Supramolecular Recognition by S⋅⋅⋅O Chalcogen Bonding in Molecular Complexes of Riluzole

Thomas

Kumar

Alhameedi

et al. 2019

Chemistry A European J

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Classical examples of supramolecular recognition units or synthons are the ones formed by hydrogen bonds. Here, we report the ubiquity of a S⋅⋅⋅O chalcogen bonded synthon observed in a series of supramolecular complexes of the amyotrophic lateral sclerosis drug riluzole. Although the potential of higher chalcogens such as Se and Te to form robust and directional chalcogen bonded motifs is known, intermolecular sulfur chalcogen bonding is considered to be weak owing to the lower polarizability of S atoms. Here, the robustness and electronic nature of a S⋅⋅⋅O chalcogen bonding non‐classical synthon, and the origin of its exceptional directionality have been explored. Bond orders of the drug–coformer chalcogen bonding are found to be as high as one third of a single bond, and they are largely ionic in nature. The contribution of the S⋅⋅⋅O chalcogen bonded motifs to the lattice energies of a series of crystals from the Cambridge Structural Database has been analyzed, showing they can be indeed significant, especially in molecules devoid of strong hydrogen bond donor groups.

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Section: Resultsmentioning

confidence: 89%

Non‐Classical Synthons: Supramolecular Recognition by S⋅⋅⋅O Chalcogen Bonding in Molecular Complexes of Riluzole

Thomas

Kumar

Alhameedi

et al. 2019

Chemistry A European J

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“…Halogen bonds (XBs) [10,24], namely interactions where an atom of a group 17 element is the electrophilic site, represent the best known subset of σ-hole interactions. Chalcogen bonds (CBs) have been studied in silico [25,26] and in the solid [27], liquid [28], and gas [29] phases. Pnictogen bonds (PBs) have received much attention in studies performed in silico [30] and in the solid [31]; and the aerogen bond (AB) is the most recently discovered subset of σ-hole interactions [32].…”

Section: Introductionmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

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Modeling indicates the presence of a region of low electronic density (a Bσ-hole^) on group 14 elements, and this offers an explanation for the ability of these elements to act as electrophilic sites and to form attractive interactions with nucleophiles. While many papers have described theoretical investigations of interactions involving carbon and silicon, such investigations of the heavier group 14 elements are relatively scarce. The purpose of this review is to rectify, to some extent, the current lack of experimental data on interactions formed by germanium and tin with nucleophiles. A survey of crystal structures in the Cambridge Structural Database is reported. This survey reveals that close contacts between Ge or Sn and lone-pair-possessing atoms are quite common, they can be either intra-or intermolecular contacts, and they are usually oriented along the extension of the covalent bond formed by the tetrel with the most electron-withdrawing substituent. Several examples are discussed in which germanium and tin atoms bear four carbon residues or in which halogen, oxygen, sulfur, or nitrogen substituents replace one, two, or three of those carbon residues. These close contacts are assumed to be the result of attractive interactions between the involved atoms and afford experimental evidence of the ability of germanium and tin to act as electrophilic sites, namely tetrel bond (TB) donors. This ability can govern the conformations and the packing of organic derivatives in the solid state. TBs can therefore be considered a promising and robust tool for crystal engineering.

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“…[49][50][51] Directional bondingb etween two divalentc halcogen centers was traced to an interaction between the occupied orbital( lone pair (LP) of electrons) at the electron-donating center and the vacant orbital( s-antibonding (s*) chalcogenÀX) at the accepting chalcogen center (YB donor). [49,[62][63][64][65] Chalcogen bondingi sg enerally accepted to be similar in nature to that of halogen bonding and is frequently described by using ESPs and the s-hole concept. [56,61] S···O, S···N, and S···S YBs involving methionine andc ysteine have been identified in proteins,a nd it has been suggested that they mayp romote protein folding and stability.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Covalence in Bifurcated Chalcogen Bonding

Bora

Novák

Novotný

et al. 2017

Chemistry A European J

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Supramolecular interactions are generally classified as noncovalent. However, recent studies have demonstrated that many of these interactions are stabilized by a significant covalent component. Herein, for systems of the general structure [MX ] :YX (M=Se or Pt; Y=S, Se, or Te; X=F, Cl, Br, I), featuring bifurcated chalcogen bonding, it is shown that, although electrostatic parameters are useful for estimating the long-range electrostatic component of the interaction, they fail to predict the correct order of binding energies in a series of compounds. Instead, the Lewis basicity of the individual substituents X on the chalcogen atom governs the trends in the binding energies through fine-tuning the covalent character of the chalcogen bond. The effects of substituents on the binding energy and supramolecular electron sharing are consistently identified by an arsenal of theoretical methods, ranging from approaches based on the quantum chemical topology to analytical tools based on the localized molecular orbitals. The chalcogen bonding investigated herein is driven by orbital interactions with significant electron sharing; this can be designated as supramolecular covalence.

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Sulfur–Oxygen Chalcogen Bonding Mediates AdoMet Recognition in the Lysine Methyltransferase SET7/9

Cited by 95 publications

References 34 publications

Non‐Classical Synthons: Supramolecular Recognition by S⋅⋅⋅O Chalcogen Bonding in Molecular Complexes of Riluzole

Non‐Classical Synthons: Supramolecular Recognition by S⋅⋅⋅O Chalcogen Bonding in Molecular Complexes of Riluzole

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Supramolecular Covalence in Bifurcated Chalcogen Bonding

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