• Bulletin of the Korean Chemical Society
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• 제29권10호
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• pp.1879-1880
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• 2008

• Bulletin of the Korean Chemical Society
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• 제30권11호
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• pp.2795-2798
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• 2009

• 대한화학회지
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• 제52권6호
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• pp.727-733
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• 2008

• Journal of Pharmaceutical Investigation
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• 제28권4호
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• pp.215-221
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• 1998

In order to elucidate the fraction of sulfoxidation in the over all in vivo metabolism of chlorpromazine (CPZ), the sulfoxidation of CPZ to chlorpromazine sulfoxide (CPZSO) was studied in rats. CPZ (10 mg/kg) and CPZSO (1 mg/kg) were injected into the rat femoral vein, respectively. And the pharmacokinetic parameters were obtained from the plasma concentration-time profiles of CPZ and CPZSO determined by the simultaneous analysis using high-performance liquid chromatography. It was supposed that these drugs were almost metabolized in vivo because the total excreted amounts of CPZ and CPZSO via urinary and biliary route were lower than 1.4% and 10.61% of the administered dose, respectively. And also, it was found that the fraction of systemic clearance of CPZ which formed CPZSO $(F_{mi})$ was 0.115. These results showed that CPZ was sulfoxized by 11.5% in rats and the residue would be metabolized via the other routes.

• Bulletin of the Korean Chemical Society
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• 제32권3호
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• pp.1063-1066
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• 2011

• Bulletin of the Korean Chemical Society
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• 제23권4호
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• pp.626-628
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• 2002

• Journal of Microbiology and Biotechnology
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• 제17권7호
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• pp.1083-1089
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• 2007

Because of their selectivity and catalytic efficiency, BVMOs are highly valuable biocatalysts for the chemoenzymatic synthesis of a broad range of useful compounds. In this study, we investigated the microbial Baeyer-Villiger oxidation and sulfoxidation of thioanisole and bicyclo[3.2.0]hept-2-en-6-one using whole Escherichia coli cells that recombined with each of the Baeyer-Villiger monooxygenases originated from Pseudomonas aeruginosa PAOl and two from Streptomyces coelicolor A3(2). The three BVMOs were identified in the microbial genome database by a recently described protein sequence motif; e.g., BVMO motif(FXGXXXHXXXW). The reaction products were identified as (R)-/(S)-sulfoxide and 2-oxabicyclo/3-oxabicyclo[3.3.0]oct-6-en-2-one by GC-MS analysis. Consequently, this study demonstrated that the three enzymes can indeed catalyze the Baeyer-Villiger reaction as a biocatalyst, and effective annotation tools can be efficiently exploited as a source of novel BVMOs.

• 대한화학회지
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• 제46권4호
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• pp.330-336
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• 2002

새로운 ${\alpha},{\beta}$-불포화Carboxanilide계열의 살균제를 개발을 목적으로 4-acetyl-3-methyl-N-phenyl-1,4-thiazine-2-Carboxamide(6)의 합성에 대하여 기술하였다. Dihydro-1,4-thiazine methyl ester 11을 산화하여 생성된 sulfoxide 7을 Pummerer 반응하여 $\alpha$-acetoxy dihydro-1,4-thiazine 10a를 얻었다. 반며에 Dihydro-1,4-thiazine Carboxanilide sulfoxide14는 동일한 반응조건 하에서 중간체 sulfonium ion의 carboxanilide기가 관여한 vinylogous Pummerer 반응의 전위에 의하여 중간체를 15를 통하여 acetoxymethyl dihydro-1,4-thiazine 18이 생성되었다. 1,4-Thiazine carboxanilide 6은 $\alpha$-acetoxy dihydro-1,4-thiazine 10a를 산촉매로 처리한 다음 생성된 21a를 가수분해하고 아닐린과 결합하여 합성하였다