Biotransformations on organic selenides and tellurides: synthetic applications

Comasseto, J. V.; Gariani, Rogério A.

doi:10.1016/j.tet.2009.06.121

Cited by 40 publications

(12 citation statements)

References 41 publications

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“…Thus, the use of chiral organochalcogen compounds represents a great opportunity for increasing the range of synthetic intermediates and bioactive compounds . Among the methods used to obtain chiral chalcogen containing secondary alcohols, biocatalytic methods have exhibited a high effectivity …”

Section: Introductionmentioning

confidence: 99%

“…18 Among the methods used to obtain chiral chalcogen containing secondary alcohols, biocatalytic methods have exhibited a high effectivity. 19 Considering the importance of organochalcogen compounds and secondary alcohol derivatives, and due to the possibility of exploring 77 Se and 125 Te NMR spectroscopy to study chirality, we report a method for NMR chiral discrimination and NMR assignment of the absolute configuration of chalcogen containing secondary alcohols. Our strategy involves the use of the 1,1′-bi-2-naphthol and 4-(dimethylamino) pyridine (BINOL/DMAP) ternary complex as a CSA and Naproxen as a CDA.…”

Section: Introductionmentioning

confidence: 99%

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NMR chiral discrimination of chalcogen containing secondary alcohols

et al. 2018

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Here, we report the general strategies by which NMR spectroscopy can be used to determine the enantiopurity and absolute configuration of chalcogen containing secondary alcohols, including the evaluation of the use of chiral solvating and chiral derivatizing agents. The BINOL/DMAP ternary complex demonstrated a simple and fast protocol for determining enantiopurity. The drug Naproxen afforded a stable, nonhygroscopic, and readily available chiral derivatizing agent (CDA) for NMR chiral discrimination of chalcogen containing secondary alcohols. The chiral recognition by CDA and chiral solvating agent (CSA) was assessed using 1H, 77Se‐{1H}, and 125Te‐{1H} NMR spectroscopy. A simple model for the assignment of the absolute configuration from NMR data is presented.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

NMR chiral discrimination of chalcogen containing secondary alcohols

et al. 2018

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“…Some of these synthesis are enantioselective thanks to the recent efforts of our group to prepare enantiomerically pure tellurium compounds by means of biocatalytic methods. 50 As can be observed, the tellurium based methodologies present superior results, especially when the Z stereoselectivity of the hydrotelluration is considered. The preparation of Z-organometallics by the classical methods is not a trivial process, 15 contrary to the straightforward way to access such species employing tellurium methodologies.…”

Section: Application Of the Te / Metal Exchange Reaction In The Synthmentioning

confidence: 94%

Reactive organometallics from organotellurides: application in organic synthesis

Princival

Santos

Comasseto

2010

J. Braz. Chem. Soc.

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Neste artigo é revisada a preparação de organometálicos reativos a partir de teluretos orgânicos. É comentado o uso dos organometálicos preparados dessa maneira na síntese de substâncias bioativas.In this paper the preparation of reactive organometallics starting from organotellurides is reviewed. The application of the reactive organometallics prepared in this way in the synthesis of bioactive compounds is commented.

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“…Despite the growing use of organotellurium compounds in chemistry and biochemistry and the consequent increase in the risk of occupational and environmental exposure to these substances, data about their toxicity are scarce in the literature. In fact, these compounds have been shown to be promising and useful alternatives for numerous synthetic operations in organic synthesis (Petragnani 1994; Comasseto and Gariani 2009). Previous studies demonstrated that organotellurium compounds are potentially toxic and lethal to rodents at low doses (Meotti et al 2003; Savegnago et al 2006) Indeed, tellurides can cause cytotoxicity (Sailer et al 2004), hepatotoxicity (Meotti et al 2003), neurotoxicity (Nogueira et al 2001; Nogueira et al 2002), teratogenicity (Stangherlin et al 2005) and genotoxicity (Santos et al 2009a, b).…”

Section: Introductionmentioning

confidence: 99%

Sub-acute administration of (S)-dimethyl 2-(3-(phenyltellanyl) propanamido) succinate induces toxicity and oxidative stress in mice: unexpected effects of N-acetylcysteine

et al. 2013

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The organic tellurium compound (S)-dimethyl 2-(3-(phenyltellanyl) propanamide) succinate (TeAsp) exhibits thiol-peroxidase activity that could potentially offer protection against oxidative stress. However, data from the literature show that tellurium is a toxic agent to rodents. In order to mitigate such toxicity, N-acetylcysteine (NAC) was administered in parallel with TeAsp during 10 days. Mice were separated into four groups receiving daily injections of (A) vehicle (PBS 2.5 ml/kg, i.p. and DMSO 1 ml/kg, s.c.), (B) NAC (100 mg/kg, i.p. and DMSO s.c.), (C) PBS i.p. and TeAsp (92.5 μmol/kg, s.c), or (D) NAC plus TeAsp. TeAsp treatment started on the fourth day. Vehicle or NAC-treated animals showed an increase in body weight whereas TeAsp caused a significant reduction. Contrary to expected, NAC co-administration potentiated the toxic effect of TeAsp, causing a decrease in body weight. Vehicle, NAC or TeAsp did not affect the exploratory and motor activity in the open-field test at the end of the treatment, while the combination of NAC and TeAsp produced a significant decrease in these parameters. No DNA damage or alterations in cell viability were observed in leukocytes of treated animals. Treatments produced no or minor effects on the activities of antioxidant enzymes catalase, glutathione peroxidase and glutathione reductase, whereas the activity of the thioredoxin reductase was decreased in the brain and increased the liver of the animals in the groups receiving TeAsp or TeAsp plus NAC. In conclusion, the toxicity of TeAsp was potentiated by NAC and oxidative stress appears to play a central role in this process.Electronic supplementary materialThe online version of this article (doi:10.1186/2193-1801-2-182) contains supplementary material, which is available to authorized users.

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Biotransformations on organic selenides and tellurides: synthetic applications

Cited by 40 publications

References 41 publications

NMR chiral discrimination of chalcogen containing secondary alcohols

NMR chiral discrimination of chalcogen containing secondary alcohols

Reactive organometallics from organotellurides: application in organic synthesis

Sub-acute administration of (S)-dimethyl 2-(3-(phenyltellanyl) propanamido) succinate induces toxicity and oxidative stress in mice: unexpected effects of N-acetylcysteine

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