Selenium is an essential microelement required for a number of biological functions. Selenium—and more specifically the amino acid selenocysteine—is present in at least 25 human selenoproteins involved in a wide variety of essential biological functions, ranging from the regulation of reactive oxygen species (ROS) concentration to the biosynthesis of hormones. These processes also play a central role in preventing and modulating the clinical outcome of several diseases, including cancer, diabetes, Alzheimer’s disease, mental disorders, cardiovascular disorders, fertility impairments, inflammation, and infections (including SARS-CoV-2). Over the past years, a number of studies focusing on the relationship between selenium and such pathologies have been reported. Generally, an adequate selenium nutritional state—and in some cases selenium supplementation—have been related to improved prognostic outcome and reduced risk of developing several diseases. On the other hand, supra-nutritional levels might have adverse effects. The results of recent studies focusing on these topics are summarized and discussed in this review, with particular emphasis on advances achieved in the last decade.
Diborylmethane can be homologated uni- and bidirectionally by using enantiomerically pure lithium-stabilized carbenoids to give 1,2- and 1,3-bis(boronic esters), respectively, in good yield and with excellent levels of enantio- and diastereoselectivity. The high sensitivity of the transformation to steric hindrance enables the exclusive operation of either manifold, effected through the judicious choice of the type of carbenoid, which can be a sparteine-ligated or a diamine-free lithiated benzoate/carbamate. The scope of the 1,2-bis(boronic esters) so generated is complementary to that encompassed by the asymmetric diboration of alkenes, in that primary–secondary and primary–tertiary 1,2-bis(boronic esters) can be prepared with equally high levels of selectivity and that functional groups, such as terminal alkynes and alkenes, are tolerated. Methods for forming C2-symmetric and non-symmetrical anti and syn 1,3-bis(boronic esters) are also described and represent a powerful route towards 1,3-functionalized synthetic intermediates.
The synthesis and the study of organoselenium compounds have received much attention over the past decades. Selenium‐containing organic molecules are widely used in organic synthesis, materials science, and medicinal chemistry. Selenium – and more specifically the amino acid selenocysteine, bearing a selenol (SeH) moiety – is present in at least 25 human protein families, whose biological functions have not been completely identified. Amongst the variety of organoselenium compounds, selenols are a versatile class of molecules easily undergoing a broad array of useful transformations. Because of the unique properties of the SeH group, selenol chemistry has important applications in chemical sciences, spanning from organic synthesis to materials chemistry and biology. This review summarises currently available methodologies for the synthesis of selenols and highlights applications of selenols in chemical sciences and biology. magnified image
6-O-L-Ascorbyl selenoesters, thioesters and telluroesters can be efficiently and directly prepared from L-ascorbic acid and suitable functionalised chalcogenoesters through lipase-catalysed transesterification reactions. Novel synthesised L-ascorbyl derivatives exhibited remarkable chain breaking and glutathione peroxidase-like activities.