Arsenicin A, A Natural Polyarsenical: Synthesis and Crystal Structure
@article{Lu2010ArsenicinAA, title={Arsenicin A, A Natural Polyarsenical: Synthesis and Crystal Structure}, author={Di-Qiu Lu and Alan David Rae and Geoffrey Salem and Michelle L Weir and Anthony C. Willis and Stanley Bruce Wild}, journal={Organometallics}, year={2010}, volume={29}, pages={32-33} }
The synthesis of the natural polyarsenical Arsenicin A and its crystal structure are described. The molecule has the adamantane-type structure of arsenic trioxide in which three of the oxygen atoms have been replaced by methylene groups to generate four arsenic stereocenters of the same configuration in each enantiomer of the racemate.
21 Citations
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- Political Science
- 2015
The theoretical contribution was supported by the Australian
Research Council (ARC) and the Australian National
Computational Infrastructure. M.L.C. gratefully acknowledges
the award of an ARC…
Origin of the unusual ultraviolet absorption of Arsenicin A.
- ChemistryThe journal of physical chemistry. A
- 2011
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- Chemistry
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- ChemistryScientific Reports
- 2017
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An overview of the biological activities of arsenic compounds containing more than one arsenic atom in their molecular structure is presented. This contribution covers the literature of the last…
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- Chemistry, BiologyOrganic & biomolecular chemistry
- 2010
New and simple protocols are described for the conversion of the enzymatically-derived and enantiomerically pure cis-1,2-dihydrocatechol (X = I) and its 6-methylated derivative into either antipodal…
References
SHOWING 1-10 OF 11 REFERENCES
Computational NMR spectroscopy of organoarsenicals and the natural polyarsenic compound arsenicin A.
- ChemistryChemistry
- 2008
It is shown that non-relativistic methods successfully model the NMR spectra of (1)H and (13)C NMR chemical shifts and coupling constants of a series of organoarsenic compounds, and application of the same methods to arsenicin A allowed several viable alternative structures to be ruled out and confirmed the previously suggested adamantane-like structure of arsenic in A.
On the first polyarsenic organic compound from nature: arsenicin A from the New Caledonian marine sponge Echinochalina bargibanti.
- ChemistryChemistry
- 2006
In defining an adamantine-type polyarsenic structure for this compound, deceptively simple NMR spectra were complemented by extensive mass spectral analysis and a comparative ab initio simulation of IR spectra for the natural and the synthetic compounds was decisive.
The potential of arsenic trioxide in the treatment of malignant disease: past, present, and future.
- MedicineLeukemia research
- 2004
Lipid encapsulation of arsenic trioxide attenuates cytotoxicity and allows for controlled anticancer drug release.
- Biology, ChemistryJournal of the American Chemical Society
- 2006
The results demonstrate that cytotoxicity can be controlled via transitions of the inorganic drug between solid and solution phases and suggest a mechanism for further improvement of the risk/benefit ratio of As2O3 in treatment of a variety of cancers.
Mechanisms of action of arsenic trioxide.
- BiologyCancer research
- 2002
Substantial data show that arsenic trioxide produces remissions in patients with APL at least in part through a mechanism that results in the degradation of the aberrant PML-retinoic acid receptor alpha fusion protein.
Zur Kenntnis des Methan‐diarsenoxids. I
- Chemistry
- 1970
Sublimiertes Methan-diarsenoxid, das bei der Hydrolyse von Methan-bis-dichlorarsin entsteht, liegt in Benzol-Losungen in dimerem Zustand als (CH2As2O2)2 vor und zeigt formale Ahnlichkeit mit dem…
Darstellung und Reaktion des Chlormethyl-dichlorarsins
- Chemistry
- 1970
Chlormethyl-dichlorarsin, ClCH2AsCl2, wird dargestellt durch Alkylieren von AsCl3 mit Bis-chlormethyl-quecksilber und durch Kommutieren von Chlormethyl-diphenyl-arsin mit AsCl3 bei 270°C. Mit…
710 73 Å ; 14 095 reflections collected
5°; absorption corrected by integration via Gaussian method implemented in maXus (2000); refinement method full-matrix least squares on F 2