Direct biocatalysed synthesis of first sulfur-, selenium- and tellurium- containing l-ascorbyl hybrid derivatives with radical trapping and GPx-like properties

Abstract

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.

Evaluation of Thio- and Seleno-Acetamides Bearing Benzenesulfonamide as Inhibitor of Carbonic Anhydrases from Different Pathogenic Bacteria

“…Finally, we further enlarge the scope of this procedure with variously substituted diselenides allowing the synthesis of organoselenides 8a-c from diselenides 6a-c and diselenides 6a,b,d,e gave N-(4-(benzylselanyl)phenyl)acetamides 9a-d, bearing two selenated moieties onto the same molecular skeleton ( Figure 2). Additionally, on the basis of our recent findings on the reactivity of selenols with elecrophiles [17][18][19][20], we also evaluated an alternative and milder approach to 2-seleno-acetamides 7-9. Thus, aryl-and alkyl-selenols 10a-d were efficiently deprotonated by using a Cs 2 CO 3 /TBAI system [21,22] and then treated with 2-chloroacetamides 2a-c to afford the corresponding selenium-containing acetamides 7-9 in good yield (Scheme 1).…”

gem-Heterosubstituted (stannyl)methylsilanes as synthetic equivalents of functionalized α-stannyl(methyl) anions

“…Organoselenides have been used as valuable synthetic intermediates, ligands, and catalysts. Furthermore, a growing number of selenium-containing small molecules has been recently demonstrated to possess an array of biological properties, including antioxidant, [23][24][25] anticancer, 26 and enzyme modulator activities. [27][28][29][30][31] The development of novel routes towards organoselenium derivatives is, therefore, highly desirable.…”

Ascorbyl‐6‐O‐oleate: A Bioconjugate Antioxidant Lipid

“…These considerations led us to explore the synthesis of innovative performing materials that combine specific properties of different moieties. For example we join the properties of vitamin C and sulphur, selenium or tellurium groups, [19] to the functional features imparted with the formation of supramolecular nanoassemblies.…”