64304-94-5Relevant academic research and scientific papers
Biocatalytical Asymmetric Sulfoxidation by Identifying Cytochrome P450 from Parvibaculum Lavamentivorans DS-1
Wu, Kailin,Tang, Linchao,Cui, Haibo,Wan, Nanwei,Liu, Ziyan,Wang, Zhongqiang,Zhang, Shimin,Cui, Baodong,Han, Wenyong,Chen, Yongzheng
, p. 5410 - 5413 (2018/11/23)
Cytochrome P450 monooxygenases (P450s) catalyzed asymmetric sulfoxidation represents a green route for the synthesis of valuable enantiopure sulfoxides, which are potentially interesting synthons in synthetic and pharmaceutical chemistry. Here the potential P450 and redox partner genes from Parvibaculum lavamentivorans DS-1 are screened and co-expressed in Escherichia coli host to construct twenty recombinant P450 strains. By testing the whole-cell biooxidation of thioanisole, P450PL2 (CYP278A4) and P450PL7 (CYP108G3) are identified with excellent S enantioselectivity while P450PL1 (CYP111B1) and P450PL9 (CYP153A26) exhibit the complementary R enantioselectivity. Asymmetric sulfoxidation of sulfides 1 a–1 m is further investigated using the recombinant E. coli strain P450PL2-2 based on the optimal conditions, producing the corresponding enantioenriched sulfoxides with up to 82 % isolated yield and 99 % ee.
A chemo-enzymatic synthesis of chiral secondary alcohols bearing sulfur-containing functionality
Chen, Qihui,Wang, Ke,Yuan, Chengye
experimental part, 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.
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
