2976-99-0Relevant academic research and scientific papers
Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase
Rioz-Martinez, Ana,Kopacz, Malgorzata,De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Gotor, Vicente,Fraaije, Marco W.
experimental part, p. 1337 - 1341 (2011/04/23)
A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides. The Royal Society of Chemistry 2011.
Turning a riboflavin-binding protein into a self-sufficient monooxygenase by cofactor redesign
De Gonzalo, Gonzalo,Smit, Christian,Jin, Jianfeng,Minnaard, Adriaan J.,Fraaije, Marco W.
supporting information; experimental part, p. 11050 - 11052 (2011/12/01)
By cofactor redesign, self-sufficient monooxygenases could be prepared. Tight binding of N-alkylated flavins to riboflavin-binding protein results in the creation of artificial flavoenzymes capable of H2O 2-driven enantioselective sulfoxidations. By altering the flavin structure, opposite enantioselectivities could be achieved, in accordance with the binding mode predicted by in silico flavin-protein docking of the unnatural flavin cofactors. The study shows that cofactor redesign is a viable approach to create artificial flavoenzymes with unprecedented activities.
Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases
Rioz-Martinez, Ana,De Gonzalo, Gonzalo,Pazmino, Daniel E. Torres,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 6409 - 6416 (2011/02/24)
Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright
Borax-catalyzed and pH-Controlled selective oxidation of organic sulfides by H2O2: An environmentally clean protocol
Hussain, Sahid,Bharadwaj, Saitanya K.,Pandey, Ravindra,Chaudhuri, Mihir K.
experimental part, p. 3319 - 3322 (2011/03/17)
The selective oxidation of sulfides to sulfoxides and sulfones was achieved in high yields at: room temperature with borax as a recyclable catalyst and H2O2 as the terminal oxidant by varying the pH of the reaction medium. The borax/H2O2 system can chemoselectively oxidize alkyl and aryl sulfides in the presence of oxidation-prone functional, groups such as C=C, -CN, and -OH.
Discovery, characterisation, and utilisation of selenoxide-sulfonic acid salts: A new class of selenoxide-based oxidant and stable selenoxide equivalent
Procter, D. John,Thornton-Pett, Mark,Rayner, Christopher M.
, p. 1841 - 1854 (2007/10/03)
The preparation and characterisation of a novel class of salts of selenoxides with sulfonic acids are described. They are readily prepared by simple addition of the sulfonic acid to a solution of selenoxide, and removal of solvent. In most cases they are colourless crystalline solids and are considerably more stable than the parent selenoxides, allowing full characterisation and X-ray crystallographic analysis. They also efficiently oxidise sulfides to sulfoxides, with no overoxidation, and clean regeneration of selenide. Their structure has been confirmed by 1H NMR spectroscopy and X-ray crystallography.
