One or More CC Bond(s) by Elimination of S, Se, Te, N, P, As, Sb, Bi, Si, Ge, B, or Metal Functions

Eustache, J.; Bisseret, P.; Weghe, Pierre van de

doi:10.1016/b0-08-044655-8/00014-3

Cited by 3 publications

(2 citation statements)

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“…The study on the chemical transformation of single organosulfide would shed some light on the key reaction principles and the factors governing the transformation in complex food matrix. Sulfoxides are known to undergo β-elimination reaction upon heating and this property has been applied in organic synthesis of olefins sulfenic acids as by-products ( 74 ). In principle, ASCOs can form sulfenic acid through thermal elimination perhaps at higher temperature cooking in food matrix.…”

Section: Transformations Of Dietary Organosulfides Under Different Prmentioning

confidence: 99%

Chemical and Biochemical Mechanisms Underlying the Cardioprotective Roles of Dietary Organopolysulfides

et al. 2015

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Foods that are rich in organosulfides are highly regarded for their broad range of functions in disease prevention and health promotion since ancient time yet modern scientific study, particularly clinical studies could not agree with traditional wisdom. One of the complexities is due to the labile nature of organosulfides, which are often transformed to different structures depending on the processing conditions. The recent evidence on polysulfides as H2S donors may open up a new avenue for establishing structure and health promotion activity relationship. To put this development into perspective, we carried out a review on the recent progress on the chemistry and biochemistry of organopolysulfides with emphasis on their cardioprotective property. First, we briefly surveyed the foods that are rich in polysulfides and their structural diversity. This is followed by in-depth discussion on the chemical transformations of polysulfides under various processing conditions. We further reviewed the potential action mechanisms of polysulfides in cardioprotection through: (a) hydrogen sulfide releasing activity; (b) radical scavenging activity; and (c) activity in enzyme inhibition and intervention of gene regulation pathways. Based on the literature trend, we can conclude that the emerging concept of organopolysulfides as naturally occurring H2S donors is intriguing and warrants further research to establish the structure and activity relationship of the organopolysulfides as H2S donors.

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Section: Transformations Of Dietary Organosulfides Under Different Prmentioning

confidence: 99%

Chemical and Biochemical Mechanisms Underlying the Cardioprotective Roles of Dietary Organopolysulfides

et al. 2015

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“…The latter outcome is surprising, and we note that stable secondary benzylic sulfoxides are known in the literature, but the addition of the ester group appears to accelerate the elimination reaction. 13 This data demonstrated that benzylic sulfoxides should be avoided in the IML designs, but that aliphatic sulfoxides are promising.…”

Section: Resultsmentioning

confidence: 92%

Design of CID-cleavable protein cross-linkers: identical mass modifications for simpler sequence analysis

et al. 2015

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The cross-linking Mass Spectrometry (XL-MS) technique has enormous potential for studying the interactions between proteins, and it can provide detailed structural information about the interaction interfaces in large protein complexes. Such information has been difficult to obtain by conventional structural methods. One of the primary impediments to the wider use of the XL-MS technique is the extreme challenge in sequencing cross-linked peptides because of their complex fragmentation patterns in MS. A recent innovation is the development of MS-cleavable cross-linkers, which allows direct sequencing of component peptides for facile identification. Sulfoxides are an intriguing class of thermally-cleavable compounds that have been shown to fragment selectively during low-energy collisional induced dissociation (CID) analysis. Current CID-cleavable cross-linkers create fragmentation patterns in MS2 of multiple peaks for each cross-linked peptide. Reducing the complexity of the fragmentation pattern in MS2 facilitates subsequent MS3 sequencing of the cross-linked peptides. The first authentic identical mass linker (IML) has now been designed, prepared, and evaluated. Multistage tandem mass spectrometry (MSn) analysis has demonstrated that the IML cross-linked peptides indeed yield one peak per peptide constituent in MS2 as predicted, thus allowing effective and sensitive MS3 analysis for unambiguous identification. Selective fragmentation for IML cross-linked peptides from the 19S proteasome complex was observed, providing a proof-of-concept demonstration for XL-MS studies on protein complexes.

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