• Archives of Pharmacal Research
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• v.26 no.12
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• pp.997-1001
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• 2003

This paper deals with chiral enzymatic resolution of 4-arylthio-2-butanols by lipase to prepare potential intermediates of $\beta$-lactam antibiotics. Among several lipases employed, lipase P type enzyme gave the highest ee value to prepare (R)-4-arylthio-2-butyl acetate. The enzymatic resolution of phenyl substituted alcohol (6a) using lipase P showed the highest ee value (99.7%) among those of 4-arylthio-2-butanol derivatives. Lipase P mediated hydrolysis of acylester 7a gave also (R)-alcohol 6a selectively. For determination of enantiomeric purity of these enzymatic resolved analytes, liquid chromatographic analysis was performed using two coupled Chiralcel OD and (R,R)-WhelkO chiral column.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.278.1-278.1
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• 2003

Recently, particular attention has been paid to the chiral separation of amino acid enantiomers because of their different biological activities. Hence, the high optical purity of aromatic amino acids is critical because of their important functions in the central nervous system. For the accurate chiral discrimination. we attempted to exploit the crosschecking each enantiomeric migraion orders of aromatic amino acids measured using (+)-18C6H4TA and (-)-18C6H4TA as the chiral selectors under pH 2.0, tris/citric acid buffer.

• Applied Chemistry for Engineering
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• v.17 no.4
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• pp.369-374
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• 2006

$Rh-Pt/Al_{2}O_{3}$ catalysts were used for the first time to study its reaction characteristics in the asymmetric hydrogenation of ethyl pyruvate. The catalysts were prepared either by impregnation of Rh on a commercial $Pt/Al_{2}O_{3}$ or by sequential impregnation of Rh followed by impregnation of Pt on $Al_{2}O_{3}$. Reaction rate and enantiomeric excess (ee%) were compared according to the preparation method, Rh contents, and the reduction temperature of the catalyst. The physical characteristics of the catalysts were analyzed using XRD and TEM. Bimetallic $Rh-Pt/Al_{2}O_{3}$ catalysts showed an improved reaction rate and optical purity (63.6 ee%) with increasing the reduction temperature. The variation of the Rh contents as well as the preparation method elicited a big difference on the reaction rate, while enantiomeric excess (ee%) was lower (56~60%) with all bimetallic catalysts than with monometallic $Pt/Al_{2}O_{3}$ catalyst.

• Journal of the Korean Chemical Society
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• v.58 no.3
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• pp.277-282
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• 2014

The optical purity of 11 commercial dexibuprofens and 7 ibuprofens sold in Korea in 2013 were examined by chiral HPLC. The Chiralcel OD-H column and LUX-Cellulose-1 column were used as chiral stationary phases and the mixed eluent of hexane:isopropanol:acetic acid as 100:1:0.1 was used as a mobile phase with a flow rate of 1.0 mL/min. Each data was obtained from an average value of at least three different experiments for each sample and the average value of relative standard deviation of them appeared very small, 0.19%. Average optical purity value (97.5%) of eleven commercial dexibuprofens used in this study were smaller than those of 9 years ago (99.2%), but larger than four years ago (95.6%). Enantiomeric ratios of (R)- and (S)-isomers of seven ibuprofen samples used in this experiment were achieved at about 50:50 which was different with the result (44:56) from four years ago.

• Applied Chemistry for Engineering
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• v.17 no.6
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• pp.658-664
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• 2006

$\rho$, $\alpha$-dimethyl benzyl alcohol was resolved by the biphasic dynamic kinetic resolution (DKR). Acidic zeolite was used as a racemization catalyst while immobilized enzyme was employed for kinetic resolution. The effects of the process variables including nature of acyl donor, reaction temperature, substrate concentration, ratio of the two catalysts and stirring rate on the conversion and enantiomeric purity of the product were investigated. In DKR of $\rho$, $\alpha$-dimethyl benzyl alcohol, the product of 99% ee was obtained with a maximum yield of 88%. The high performance of the catalyst system was maintained in the condition of higher TON and under repeated use.

• Journal of Radiopharmaceuticals and Molecular Probes
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• v.6 no.2
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• pp.75-91
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• 2020

[^99mTc]Tc-Hexamethylpropylene amine oxime (HMPAO) is currently used as a regional cerebral blood flow imaging agent for single photon emission computed tomography (SPECT). The HMPAO ligand exists in two isomeric forms: d,l and meso showing different properties in vivo. Later studies indicated that brain uptake patterns of ^99mTc-complexes formed from separated enantiomers differed. Separation of enantiomers is difficult by fractional crystallizations method. Usually, the substance is obtained in low chemical yield in a time-consuming procedure. Furthermore, the final product still contains some impurity. So we have developed new efficient route for synthesis of R,R- and S,S-HMPAO enantiomeric compounds in 6-steps. Nucleophilic substitution (S_N2) reactions of 2,2-dimethylpropane-1,3-diamine either with S- (1a) or R-methyl2-chloropropanoate (1b) were performed to produce compounds R,R- (2a) or S,S-isomer (2b) derivatives protected with benzylchloroformate (Cbz), respectively. And then Weinreb amide and methylation reaction using Grignard reagent, oxime formation with ketone group and deprotectiion of Cbz group by hydrogenolysis gave S,S- (7a) or R,R-HMPAO (7b), respectively. Entaniomeric compounds were synthesied with high yield and purity without any undesired product. The 7a or 7b kits containing 10 ㎍ SnCl₂-2H₂O were labeled with ^99mTc with high radiolabeling yield (90%).