Sulfenic acid – derived glycoconjugated disulfides and sulfoxides: a biological evaluation on human red blood cells (original) (raw)
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Unsymmetrical Target Disulfides from Transient Sulfenic Acids
Phosphorus, Sulfur, and Silicon and the Related Elements, 2011
In accordance with our research interests devoted to the development of synthetic procedures that involve sulfenic acids as intermediates, their coupling with various thiols has been exploited as an easy and versatile methodology to obtain unsymmetrical disulfides. Even if the above-mentioned reaction is well known in the literature, to the best of our knowledge it has never been used before as a methodology to obtain unsymmetrical disulfides. The mild generation of mono-, di-and trisulfenic acids from different sulfoxide precursors, depending on the required reaction conditions, allows the presence of even base/acid-sensitive and thermolabile functional groups and the synthesis, in excellent yields, of various kind of unsymmetrical disulfides, some of which carrying naturally occurring residues.
Recent Advances and Perspectives in the Chemistry of Sulfenic Acids
Current Organic Chemistry, 2007
This review (56 references) provides a comprehensive survey of the literature on sulfenic acid chemistry from 1990 through June 2006, focusing the attention on salient aspects of their structures and involvement in organic processes. Even if the majority of known sulfenic acids cannot be isolated, some stable ones have been obtained, and their study helped dramatically the comprehension of chemical and physical properties of all sulfenic acids and indirectly of the role that Cys-SOHs play in protein biochemistry. Many papers have been published in the last fifteen years about the sulfenic acid intermediacy in organic chemistry. Once generated, they can be involved in intra-and intermolecular additions to unsaturated molecules. Few examples of sulfenic acid addition to double bonds have been recently described and most of them are intramolecular processes, whereas the addition of enantiopure sulfenic acids onto carbon-carbon triple bonds has been widely exploited in the synthesis of vinyl sulfoxides to be used in many stereoselective transformations. The thermic -elimination from sulfinyl precursors is a way to generate sulfenic acids but it has been also used for removing the sulfinyl moiety from organic molecules and forming double bonds with controlled stereochemistry. Some significant applications of extrusion processes are also described in the present review.
Efficient Synthesis of Unsymmetrical Disulfides through Sulfenic Acids
European Journal of Organic Chemistry, 2009
Keywords: Sulfur / Selenium / Sulfenic acids / Alkenes / Michael addition A general procedure for the synthesis of α-(phenylseleno)sulfinyl and -sulfonyl alkenes has been described. 1-(Phenylseleno)ethenyl sulfoxides were prepared by the syn-addition of in situ-generated sulfenic acids on to the triple bond of suitably substituted (phenylseleno)acetylenes. 1-(Phenylseleninyl)ethenyl sulfones were obtained by further oxidation of their sulfinyl analogues. The mild conditions of the sulfenic acid/(phenylseleno)alkyne syn-addition and its stereospecificity and regioselectivity allowed us to obtain elec-
Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products
2018
Sulfenic acids as small molecules are too unstable to be isolated and their transient nature offers the possibility to involve them in concerted processes that lead to the obtainment of functional groups such as sulfoxides, sulfones and disulfides. All these functions are present in a number of natural and synthetic drugs and can represent structural motives inducing biological relevant properties. In this small review the generation and reactions of sulfenic acid bearing naturally occurring residues are described. Carbohydrate and aminoacid-derived sulfenic acids have been used in concerted addition to triple bonds to obtain alliin derivatives and thiosugars in enantiomerically pure form. Glycoconjugates with sulfinyl, sulfonyl and disulfane functional groups and pyridine-derived disulfides have been obtained from bis and tris-sulfinyl precursors of sulfenic acids. Small families of such compounds have been subjected to preliminary biological tests. Starting from the evidence that ...
2,2-Bis(phenylsulfonyl)ethyl sulfides as efficient precursors of sulfenic acids
Arkivoc, 2009
The use of 2,2-bis(phenylsulfonyl)ethyl sulfides as efficient precursors of sulfenic acids is reported. These starting compounds, carrying both sulfone and sulfide residues, are obtained in one step from commercially available thiols and 1,1-bis(phenylsulfonyl)ethylene. Mild decomposition of the derived 2,2-bis(phenylsulfonyl)ethyl sulfoxides to sulfenic acids, in the presence of suitable acceptors, opens the way to the generation of a wide library of new sulfoxides not easily accessible through different synthetic pathways.
Tetrahedron, 2004
Tolueneand naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfoxide diastereoisomers, formed from the reaction of the (R)-1,3-benzodithiole-1-oxide metabolite with n-butyllithium and benzaldehyde, were separated and stereochemically assigned. Treatment, of enantiopure (1R,3R)-benzo-1,3-dithiole-1,3-dioxide, obtained by chemoenzymatic synthesis, with alkyllithium reagents, resulted in a novel ring-opening reaction which proceeded with inversion of configuration to yield a series of acyclic disulfoxides. q
2019
A large variety of organosulfur compounds have been shown to having diverse biological effects such as anti-oxidant effects, anti-inflammatory properties, inhibition of platelet aggregation, reduction of systolic blood pressure, and reduction of cholesterol. Among these, sulfoxides and sulfones show wide and significant applications as commodity chemical in various fields of chemistry. Therefore, synthesis of sulfoxides as well as sulfones has remained a point of attraction for synthetic organic chemists. Among array of methods used to synthesize the sulfoxides or sulfones, oxidation of sulfide is the most convenient way. This review precises chemoselective methods for the synthesis of the sulfoxides as well as sulfones focusing on oxidative protocols. This review will aid researchers to explore and utilise the mentioned protocols for different organic transformations.
Synthesis of sulfides under solvent- and catalyst-free conditions
Monatshefte für Chemie - Chemical Monthly, 2009
A simple, highly efficient, and green protocol has been developed for preparation of sulfides from alkyl or aryl thiols and benzyl-, allyl-, t-butyl, and adamantyl halides under solvent-and catalyst-free conditions.