Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen

Shaikh, Taimur A.; Bakus, Ronald C.; Parkin, Sean; Atwood, David A.

doi:10.1016/j.jorganchem.2005.12.034

Cited by 40 publications

(37 citation statements)

References 22 publications

(30 reference statements)

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“…Structurally, the bond lengths seen in 1 for As-S bonds are consistent with previously published compounds, for example 1,2-bis-dithiarsolan-2-ylmercapto-ethane [4]. The As-S bonds in 1 range from 2.23 Å to 2.29 Å .…”

Section: Discussionsupporting

confidence: 88%

“…This is well established for six-membered rings and can be seen in the two compounds reported here as well [5]. The present work will add to the understanding of group 15 dithiolate compounds with the structure and characterization of bis(2-(1,3,2-benzodithiarsol-2ylsulfanyl)-benzenesulfide) (1) and 2-chloro-benzo-1,3,2-dithiastibole (2) [4]. …”

Section: Introductionsupporting

confidence: 77%

“…Recent interest in arsenic thiolates as building blocks in self-assembled macrocycles [2,3] along with a lack of single crystal X-ray structural analysis of relatively simple arsenic thiolates has prompted our work on the synthesis and characterization of several arsenic dithiolates [4]. These are of the general formula RS 2 AsX where R is an organic group connecting the sulfurs and X = Cl or I.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of a rare arsenic trithiolate with an organic disulfide linkage and 2-chloro-benzo-1,3,2-dithiastibole

Shaikh

Parkin

Atwood

2006

Journal of Organometallic Chemistry

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Section: Discussionsupporting

confidence: 88%

Section: Introductionsupporting

confidence: 77%

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of a rare arsenic trithiolate with an organic disulfide linkage and 2-chloro-benzo-1,3,2-dithiastibole

Shaikh

Parkin

Atwood

2006

Journal of Organometallic Chemistry

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“…1. Refinement of structure with the As(III)-S distance to 2.25 Å restrained to 2.25 Ϯ 0.05 Å resulted in a mean As-S bond distance of 2.28 Å and S-As-S angles of 91°, 92°, and 88°, which are similar to small molecule As-S 3 complexes in the literature (6,36,37). The orientation of the leucine residues in the layer above (Leu 5) and below (Leu 12) the metal-binding site differ, as seen in Fig.…”

Section: Resultssupporting

confidence: 64%

“…However, no x-ray or NMR structures of ArsR, the repressor protein, or ArsD have been reported to date. Furthermore, AsS 3 structures have not been reported for any biologically relevant small-molecule thiolates, such as glutathione, and only a handful of related AsS 3 complexes with aromatic ligands or chelated alkyl dithiolate coordination are reported (6).…”

mentioning

confidence: 99%

Identifying important structural characteristics of arsenic resistance proteins by using designed three-stranded coiled coils

Touw

Nordman

Stuckey³

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

154

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Arsenic, a contaminant of water supplies worldwide, is one of the most toxic inorganic ions. Despite arsenic's health impact, there is relatively little structural detail known about its interactions with proteins. Bacteria such as Escherichia coli have evolved arsenic resistance using the Ars operon that is regulated by ArsR, a repressor protein that dissociates from DNA when As(III) binds. This protein undergoes a critical conformational change upon binding As(III) with three cysteine residues. Unfortunately, structures of ArsR with or without As(III) have not been reported. Alternatively, de novo designed peptides can bind As(III) in an endo configuration within a thiolate-rich environment consistent with that proposed for both ArsR and ArsD. We report the structure of the As(III) complex of Coil Ser L9C to a 1.8-Å resolution, providing x-ray characterization of As(III) in a Tris thiolate protein environment and allowing a structural basis by which to understand arsenated ArsR.arsenic-binding proteins ͉ coiled coil peptides ͉ crystallography ͉ heavy metal toxicity ͉ protein design A rsenic toxicity is a worldwide problem as a natural contaminant of water supplies. Despite the fact that it is a human toxin and carcinogen, few structural reports on its interaction with biological ligands have appeared. Escherichia coli and other bacteria have evolved a detoxification mechanism that employs the arsRDABC operon (1). Arsenic removal by these encoded proteins is initiated when As(III) binds to ArsR, resulting in the dissociation of the repressor protein from the promoter DNA. The structure of the ArsA component of the ATP-dependent extrusion pump ArsAB with antimonite bound in close proximity to the nucleotide-binding site was able to provide some insight into the active transport of As(III) out of the cell (2). Additionally, structural characterization of substrate and product complexes of the arsenate reductase ArsC, which reduces arsenate (AsO 4 3Ϫ ) to arsenite (AsO 2 Ϫ ), has helped elucidate this step of the arsenic detoxification pathway (3, 4). Recent studies of E. coli ArsD indicate that it is a metallochaperone, transporting As(III) to ArsA for extrusion (5). Extended x-ray absorption fine structure and mutagenesis studies have shown that ArsR coordinates As(III) with three cysteine thiolates at a distance of 2.25 Å, a coordination mode that ArsD is also proposed to employ (1, 5). However, no x-ray or NMR structures of ArsR, the repressor protein, or ArsD have been reported to date. Furthermore, AsS 3 structures have not been reported for any biologically relevant small-molecule thiolates, such as glutathione, and only a handful of related AsS 3 complexes with aromatic ligands or chelated alkyl dithiolate coordination are reported (6).We set out to model the putative As(III) coordination environments of ArsR and ArsD in a designed peptide system. Previously, we have shown that the three-stranded coiled coildesigned with the heptad repeat strategy, such as TRI L16C (sequences of all peptides are in Table 1...

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Mass Spectrometry and Gas‐phase Ion Chemistry of Metal–phenolate and Metal–phenol complexes

Palii

Indricean

Revenco

2014

Patai's Chemistry of Functional Groups

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The current chapter summarizes 276 references to offer an up‐to‐date survey of literature on the mass spectrometry and gas‐phase ion chemistry of phenolate‐ or phenol‐containing metal complexes and their chalcogenide thio‐ and seleno‐analogs. Analytical applications of MS techniques to the characterization of these metal–ligand systems are discussed. The latter include more than 400 species such as mixed‐ligand metal complexes, bifunctional compounds containing organometallic and classical Werner‐type coordination sites, nanoclusters, species with metal–metal bonds, mixed‐metal complexes, etc. Some of them are isomers. The reviewed data provides the reader with a solid foundation for selecting the adequate MS instrumentation in related future studies. Data on gas‐phase ion structure, energetics and reactivity are summarized as well. Circa 150 examples of ion/molecule reactions with the participation of metal‐containing ions and phenol or thiophenol derivatives are examined. Additionally, the review addresses the 3D structural features of several model complexes between metal ions and phenol‐ or thiophenol‐related species as determined from theoretical calculations and IRMPD spectroscopic measurements, as well as their use for elucidation of the nature of metal cation–π interaction or σ‐binding, which mimic the active centers of biomolecular systems.

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Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen

Cited by 40 publications

References 22 publications

Synthesis and characterization of a rare arsenic trithiolate with an organic disulfide linkage and 2-chloro-benzo-1,3,2-dithiastibole

Synthesis and characterization of a rare arsenic trithiolate with an organic disulfide linkage and 2-chloro-benzo-1,3,2-dithiastibole

Identifying important structural characteristics of arsenic resistance proteins by using designed three-stranded coiled coils

Mass Spectrometry and Gas‐phase Ion Chemistry of Metal–phenolate and Metal–phenol complexes

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