32854-09-4Relevant articles and documents
Biosynthetic selenoproteins with genetically-encoded photocaged selenocysteines
Rakauskaite, Rasa,Urbanavi?iute, Giedre,Ruk?enaite, Audrone,Liutkevi?iute, Zita,Ju?kenas, Robertas,Masevi?ius, Viktoras,Klima?auskas, Saulius
, p. 8245 - 8248 (2015)
Selenocysteine is a valuable component of both natural selenoproteins and designer biocatalysts; however the availability of such proteins is hampered by technical limitations. Here we report the first general strategy for the production of selenoproteins via genetically-encoded incorporation of a synthetic photocaged selenocysteine residue in yeast cells, and provide examples of light-controlled protein dimerization and targeted covalent labeling in vitro.
Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
Alves, Diego,Sacramento, Manoela Do,Santi, Claudio,Schwab, Ricardo S.,Teixeira, Wystan K. O.,Yano De Albuquerque, Danilo
supporting information, (2022/01/12)
A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity
Schlatzer, Thomas,Schr?der, Hilmar,Trobe, Melanie,Lembacher-Fadum, Christian,Stangl, Simon,Schl?gl, Christoph,Weber, Hansj?rg,Breinbauer, Rolf
supporting information, p. 331 - 336 (2019/11/16)
The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).