66536-73-0Relevant academic research and scientific papers
A chemo-enzymatic synthesis of chiral secondary alcohols bearing sulfur-containing functionality
Chen, Qihui,Wang, Ke,Yuan, Chengye
scheme or table, p. 972 - 975 (2010/08/21)
A facile method for the preparation of chiral secondary alcohols bearing a sulfur-containing functionality using a chemo-enzymatic approach is described, with the aid of baker's yeast and Candida Antarctica lipase B. A complete set of four stereoisomers o
Formation of single diastereomers of β-hydroxy-sulfoxides by biotransformation of β-ketosulfides using Helminthosporium species NRRL 4671
Holland, Herbert L.,Ihasz, Nancy,Lounsbery, Brendan J.
, p. 640 - 642 (2007/10/03)
Single biotransformations of 1-(phenylthio)-2-propanone and 1-(p-methoxyphenylthio)-2-propanone by the fungus Helminthosporium species NRRL 4671 resulted in both sulfur oxidation to the sulfoxide and carbonyl reduction to the alcohol. The corresponding (SS,SC)-1-sulfinyl-2-propanols were obtained as single diastereomers following simple crystallization.
Electrochemical enzymatic deoxygenation of chiral sulfoxides utilizing DMSO reductase
Abo, Mitsuru,Dejima, Makiko,Asano, Fumioki,Okubo, Akira,Yamazaki, Sunao
, p. 823 - 828 (2007/10/03)
Preparation of enantiomerically enriched sulfoxides by an electrochemical enzymatic system utilizing DMSO reductase was studied. This system consists of a glassy carbon electrode as the working electrode, methyl viologen as the mediator and DMSO reductase
Chemistry of oxaziridines. 17. N-(phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine: A highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides
Davis, Franklin A.,Thimma Reddy,Han, Wei,Carroll, Patrick J.
, p. 1428 - 1437 (2007/10/02)
The synthesis, structure, and enantioselective oxidations of a new chiral N-sulfonyloxaziridine 12c [3,3-dichloro-1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2, 3'-oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)- or (-)-camphor in 50% overall yield. Steric effects are primarily responsible for the molecular recognition and are predictable using a simple active-site model where the nonbonded interactions between the RL and RS groups of the sulfide (RL-S-RS) and the active-site surface are minimized in a planar transition-state structure. The fact that alkyl aryl sulfides give high ee's in nonpolar solvents suggests that there is also a stereoelectronic component to the molecular recognition. High ee's (>90%) are anticipated for those sulfides where the difference in size of the groups directly bonded to the sulfur atom is large, i.e., aryl, tert-butyl vs CH2R (R = H, alkyl, benzyl, etc). The X-ray structure and studies with the dihydro, difluoro, and dibromo oxaziridines 12a, 12b, and 12d reveal that the exceptional enantioselectivities displayed by 12c are a consequence of a molecular cleft or groove, defined by the oxaziridine chlorine atoms and phenylsulfonyl group, on the active-site surface.
Switching of the Direction of Enzyme-Mediated Oxidation and Reduction of Sulfur-Substituted 2-Propanols and 2-Propanones
Ohta, Hiromichi,Kato, Yasuo,Tsuchihashi, Gen-ichi
, p. 2735 - 2739 (2007/10/02)
Incubation of 1-(phenylsulfenyl)-2-propanone with Corynebacterium equi IFO 3730 grown on hexadecane at pH 6.5 afforded the corresponding 1-substituted S propanols. 1-(Phenylsulfinyl)-2-propanone was also reduced by the microorganism, the product being aff
pH DEPENDENT OXIDATION-REDUCTION OF 1-BENZENESULFENYL-2-PROPANONE AND ITS OXIDES BY A MICROORGANISM
Ohta, Hiromichi,Kato, Yasuo,Tsuchihashi, Gen-ichi
, p. 581 - 584 (2007/10/02)
Incubation of 1-benzenesulfenyl-2-propanone with Corynebacterium equi IFO 3730 in a weakly acidic medium afforded (S)-1-benzenesulfenyl-2-propanol.On the contrary, when the cultivation was carried out at pH 8 with the same bacterium, only the (S)-alcohol
