• Natural Product Sciences
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• 제27권3호
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• pp.161-168
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• 2021

The chemical investigation of the 90% EtOH extract from Cicadidae Periostracum led to the isolation and identification of seven known N-acetyldopamine dimers (1-7). These compounds were identified by comparing mass spectrometry data and NMR spectroscopic data with those previously reported. In this study, complete interpretation of 1D and 2D NMR data of 1 and 2 were reported for the first time. In addition, compounds 3 and 4 were isolated from this material for the first time. All isolates were obtained as racemic mixtures, as confirmed by chiral HPLC. Furthermore, we evaluated the neuroprotective activities of compounds 1-7 and found that compounds 1, 5, and 6 significantly attenuated rotenone-induced death of SH-SY5Y neuroblastoma cells at a concentration of 100 μM. Parallel to this result, compounds 3 and 6 displayed antioxidant effects in the cytoplasm, as determined by CM-H2DCFDA fluorescence intensity, while compounds 1 and 5 showed antioxidant effects in the mitochondria, as assessed by MitoSox fluorescence intensity. Overall, these results suggest that some of these compounds protect neuroblastoma cells by ameliorating the release of reactive oxygen species. Further studies are warranted to elucidate the underlying mechanisms by which these compounds exhibit antioxidant and neuroprotective actions.

• 대한화학회지
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• 제33권4호
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• pp.426-430
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• 1989

아미노 알콜에서 합성한 티아졸리딘치온 [4-(S)-IPTT, 4(S)-ETT]은 주석을 매개체로한 알돌 축합반응의 키랄 보조제로 이용되었다. Stannous triflate와 3-아세틸티아졸리딘-2-티온을 반응시켜 얻은 2가주석 엔올레이트를 어키랄 알데히드와 반응시켜 ${\beta}$-하이드록시 카르보닐 화합물을 입체선택적으로 얻었다. 이러한 키랄 보조제는 가메탄올 분해반응으로 쉽게 에스터화 되기 때문에 절대구조 동정을 용이하게 하는 장점도 있었다.

• 한국정보디스플레이학회:학술대회논문집
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• 한국정보디스플레이학회 2002년도 International Meeting on Information Display
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• pp.933-935
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• 2002

In this paper, new non-chiral molecules with semi-fluorinated alkyl chains were synthesized varying the structure of central bent core unit. Their mesomorphic properties were investigated by DSC and polarized microscopy. The compound with 1,3-dihydroxy phenylene unit could form an enantiomeric smectic phase, but the remaining compounds with bent-core mesogenic unit were not liquid crystalline. In this presentation, their x-ray measurement and electro-optical property will be also described.

• 한국미생물·생명공학회지
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• 제24권2호
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• pp.213-216
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• 1996

Optically active carboxylic acid, D-(-)-$\beta$-hydroxyisobutyric acid {(D)-(-)-HIBA} is a useful chiral starting material for the preparation of enantiomerically pure bioactive compounds which have a chiral methyl carbon center in the molecule such as captopril, $\alpha$-tocopherol, erythromycin A, muscone and so on. (S)-3-Acetoxy-2-methylpropanol can be used as the precursor of (D)-(-)-HIBA, that is, chemical oxidation of the hydroxyl group and subsequent hydrolysis of acyl group in (S)-3-acetoxy-2-methylpropanol affords D-(-)-$\beta$-hydroxyisobutyric acid. (S)-3-Acetoxy-2-methyl-propanol was prepared by lipase-catalyzed asymmetric hydrolysis. In the enzymatic hydrolysis system, lipase AY (Candida rugosa) provided the expected (S)-3-acetoxy-2-methylpropanol in 60% e.e. of the enantiomeric purity under the phosphate buffer and organic co-solvent system.

• Biotechnology and Bioprocess Engineering:BBE
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• 제7권2호
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• pp.57-66
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• 2002

This review focuses on the use of immobilized lipase technology for the hydrolysis of oils. The importance of lipase catalyzed fat splitting process, the various immobilization procedures, kinetics, deactivation kinetics, New immobilized lipases for chiral resolution, reactor configurations, and process considerations are all reviewed and discussed.

• Bulletin of the Korean Chemical Society
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• 제30권2호
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• pp.389-396
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• 2009

MFI structural zeolite (ZSM-5 or Sililcalite) was treated with HF solution to introduce mesoporous channels in the microporous crystals. Inner mesopore size could be controlled from 2.5 to 3.5 nm by changing the concentration of HF solution. The pore structure of HF-treated MFI zeolite was studied by instrumental analysis. The active Co (III) salen complex monomers were successfully anchored non-covalently on the surfaces of mesoporous MFI-type zeolite. These heterogeneous catalysts could be applied in asymmetric ring opening of terminal epoxides by phenol derivatives. It showed very high enantioselectivity and yield up to 95% in the catalytic synthesis of optically active $\alpha$-aryloxy alcohol compounds.

• Bulletin of the Korean Chemical Society
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• 제8권5호
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• pp.421-423
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• 1987

The chiral B-isopinocampheyl-9-borabicyclo[3.3.1]nonane-potassium hydride (IPC-9-BBN-KH) and potassium B-isopinocampheyl-9-boratabicyclo[3.3.1]nonane (K IPC-9-BBNH) systems were applied to the enantioselective reduction of representative racemic epoxides, namely 1,2-epoxybutane, 1,2-epoxyoctane, 3,3-dimethyl-1,2-epoxybutane and styrene oxide. In the case of IPC-9-BBN-KH system, the optical yields are in the range of 8.3-37.4$\%$ ee. However, the system of K IPC-9-BBNH provides significantly lower optical yields, showing 7-22.5$\%$ ee. These results strongly suggest that the enantioselective coordination of chiral organoborane to the epoxy oxygen of racemic epoxides plays an important role in this resolution.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.179.1-179.1
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• 2003

Chiral building blocks have the importance in the pharmaceutical and agrochemical industries as well as in the development of rapid and efficient syntheses of bioactive compounds and natural product. Vinylstannane contains two synthetically useful functional groups (vinylstannane and allylic alcohol). The vinylstannane functional group can be used in C-C bond formation under a variety of conditions and the allylic alcohol functional can be used in hydroxyl-directed epoxidations, cyclopropanations, and sigmatropic rearrangements. (omitted)

• 청정기술
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• 제22권2호
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• pp.75-81
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• 2016

문명의 발달과 더불어 경제적으로 생활이 윤택하여지고 산업기술이 고도화 되어감에 따라 평균수명이 급격히 연장되었고, 건강식품과 의약품에 대한 의존도와 수요도 급격하게 증가하는 추세이다. 최근에는 건강식품과 의약품의 부작용이 사회적인 이슈로 등장하고 부작용이 없는 의약품의 개발, 환경과 식품산업의 건전성 향상을 위해 신속 간편하며 정확하게 건강과 환경을 계측할 수 있는 기술의 개발 또한 시급한 과제로 부각되고 있다. 의약품의 생산 공정뿐만 아니라 소비자 스스로 자기 건강을 자가 진단하고자 하며, 자기가 먹는 음식의 안전성 여부와 자기가 사는 환경의 안전성 여부를 스스로 확인하고자 하는 욕구 또한 증대되고 있다. 본고에서는 키랄 의약품, 기존의 키랄 의약품 분리기술, 분자자기인식 기법, 그리고 분자자기인식 기법에 의한 키랄 의약품 분리기술 개발동향에 대한 간단한 소개와 분자자기인식 기법에 의한 키랄 의약품 분리ㆍ분석 기술 개발 현황과 그 시장성에 대해 고찰하고자 한다.

• 분석과학
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• 제32권5호
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• pp.163-172
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• 2019

Methamphetamine (MA) is currently the most abused illicit drug in Korea and its major metabolite is amphetamine (AP). As MA exist as two enantiomers with the different pharmacological properties, it is necessary to determine their respective amounts in a sample. Thus a chiral stationary phase liquid chromatography-tandem mass spectrometric (LC-MS/MS) method was developed for identification and quantification of d-MA, l-MA, d-AP, and l-AP in human urine. Urine sample ($200{\mu}L$) was diluted with pure water and purified using solid-phase extraction (SPE) cartridge. A $5-{\mu}L$ aliquot of SPE treated sample solution was injected into LC-MS/MS system. Chiral separation was carried out on the Astec Chirobiotic V2 column with an isocratic elution for each enantiomer. Identification and quantification of enantiomeric MA and AP was performed using multiple reaction monitoring (MRM) detection mode. Linear regression with a $1/x^2$ as the weighting factor was applied to generate a calibration curve. The linear ranges were 25-1000 ng/mL for all compounds. The intra- and inter-day precisions were within 3.6 %, while the intra- and inter-day accuracies ranged from -5.4 % to 11.8 %. The limits of detection were 2.5 ng/mL (d-MA), 3.5 ng/mL (l-MA), 7.5 ng/mL (d-AP), and 7.5 ng/mL (l-AP). Method validation parameters such as selectivity, matrix effect, and stability were evaluated and met acceptance criteria. The applicability of the method was tested by the analysis of genuine forensic urine samples from drug abusers. d-MA is the most common compound found in urine and mainly used by abusers.