• Food Science and Biotechnology
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• v.17 no.2
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• pp.228-233
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• 2008

Considerable progress has been made in functionalization of the soy isoflavones through enzymatic modification of daidzin, genistin, and glycitin. After hydrolysis of $\beta$-glucosides into their corresponding aglycones, these compounds were structurally modified via biotransformations such as regioselective hydroxylation, enantioselective reduction, regioselective methylation, and polymerization. These reactions often resulted in an increase of the biological activities (e.g., anti oxidative activity, antiproliferative activity) and/or improvement of the physico-chemcial properties (e.g., water solubility, bioavailability). This review briefly summarizes on-going research activities on the biofunctionalization of the soy isoflavones.

• Bulletin of the Korean Chemical Society
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• v.27 no.6
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• pp.857-862
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• 2006

The catalytic enantioselective Michael reaction promoted by quaternary ammonium salts from Cinchona alkaloids as a phase-transfer catalyst is described. Treatment of malonates with $\alpha$,$\beta$-unsaturated ketones under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses.

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.2960-2964
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• 2011

The efficient asymmetric hydrosilylation of imines in the presence of polymethylhydrosiloxane has been investigated by screening chiral diamine-zinc complexes. A series of chiral diamine ligands were prepared from optically pure 1,2-diphenyl-1,2-ethanediamine and screened for effectiveness. N-Benzylic substituents were required for high enantioselectivity; ligands with bulky groups or extra coordinating groups such as OH and S lowered the catalytic activity. The level of asymmetric induction was usually in >90% ee range for aromatic imine substrates. A linear correlation between the ee of the ligand and that of the product was observed, indicating the presence of a 1:1 ratio of ligand to metal coordination in the active catalytic complex.

• 한국생물공학회:학술대회논문집
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• 2003.04a
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• pp.435-438
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• 2003

Epoxide hydrolase(EH) catalyze the enantioselective hydrolysis of racemic epoxides to corresponding diols. A recombinant Pichia pastoris with EH from Rhodotorula glutinis has been constructed by reverse transcriptase-polymerase chain reaction(RT-PCR). The recombinant biocatalyst enantioselectively hydrolyze (R)-styrene oxide faster than (S)-enantiomer. The catalytic activity of recombinant biocatalyst was 7-fold higher than that of wild-type strain. The recombinant EH biocatalyst can be used for kinetic resolution for the production of enantiopure styrene oxide.

• Proceedings of the Korean Society of Life Science Conference
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• 2005.09a
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• pp.91-91
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• 2005

• Bulletin of the Korean Chemical Society
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• v.35 no.6
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• pp.1590-1600
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• 2014

Cinchona-based bifunctional catalysts have been extensively employed in the field of organocatalysis due to the incorporation of both hydrogen-bonding acceptors (quinuclidine) and hydrogen-bonding donors (e.g., alcohol, amide, (thio)urea and squaramide) in the molecule, which can simultaneously activate nucleophiles and electrophiles, respectively. Among them, cinchona-derived (thio)urea and squaramide catalysts have shown remarkable application potential by using their bifurcated hydrogen bonding donors in activating electrophilic carbonyls and imines. However, due to their bifunctional nature, they tend to aggregate via inter- and intramolecular acid-base interactions under certain conditions, which can lead to a decrease in the enantioselectivity of the reaction. To overcome this self-aggregation problem of bifunctional organocatalysts, we have successfully developed a series of sulfonamide-based organocatalysts, which do not aggregate under conventional reaction conditions. Herein, we summarize the recent applications of our cinchona-derived sulfonamide organocatalysts in highly enantioselective methanolytic desymmetrization and decarboxylative aldol reactions. Immobilization of sulfonamide-based catalysts onto solid supports allowed for unprecedented practical applications in the synthesis of valuable bioactive synthons with excellent enantioselectivities.

• Bulletin of the Korean Chemical Society
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• v.34 no.12
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• pp.3591-3596
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• 2013

The enantioselective aza-Morita Baylis Hillman reaction of nitroalkene and N-tosylimine catalyzed by thiourea-tertiary amine has been investigated using density functional theory. Enantioselectivity is dominated by the cooperative effect of non-covalent and weak covalent interactions imposed by different units of catalyst. As Lewis base, the tertiary amine unit activates nitroalkene via weak covalent bond. The weak covalent interaction orients the reaction in a major path with smaller variations of this bond. The aromatic ring unit activates N-tosylimine via ${\pi}-{\pi}$ stacking. The non-covalent interaction selects the major path with smaller changes of the efficient packing areas. Thiourea unit donates more compact H-bonded network for species of the major path. The calculated ee value in xylene solution phase (97.6%) is much higher than that in N,N-Dimethylformamide (27.2%). Our conclusion is also supported by NBO analysis.

• Journal of the Korean Chemical Society
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• v.33 no.4
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• pp.426-430
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• 1989

Amino alcohol-derived thiazolidinethiones [4-(S)-IPTT, 4(S)-ETT] serve as efficient chiral auxiliary in tin medicated aldol condensation. A highly enantioselective aldol-type reaction forming various ${\beta}$-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehyde is achieved via divalent tin enolate. The other advantages of these chiral auxiliaries were the ease of removal by methanolysis.

• Proceedings of the Korean Society of Toxicology Conference
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• 2001.10a
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• pp.197-197
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• 2001

The effect of CYP2C19 genetic polymorphism on the disposition of lansoprazole enantiomers was determined in order to evaluate the contribution of CYP2Cl9 in the stereoselective metabolism of lansoprazole. After single oral dose of 30mg lansoprazole racemate in 6 subjects with CYP2C19 PM genotype and 6 with EM genotype, the plasma concentrations of R-enantimers were consistently higher than those of S-enantiomer in boty EM and PM subjects.(omitted)

• Proceedings of the Korean Vacuum Society Conference
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• 2011.02a
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• pp.332-332
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• 2011

The adsorption and desoprtion properties on Pt(111) of chiral molecules, propylene oxide (PO) and 1,3-dimethyl butylamine (DMBA), have be characterized in utrahigh vacuum. Precision-doses of PO and DMBA onto a Pt(111) surface at 90 K have been achieved with a directed tubular molecular doser controlled by a micron-sized orifice and the reservoir gas pressure. Temperature-programmed desorption (TPD) mass spectra have been employed together with low-energy electron diffraction (LEED) analyses. In addition to the separate adsorption behaviors of PO and DMBA, the enantioselective adsorption of R- and S-PO on Pt(111) precovered with R- or S-DMBA have been investigated thoroughly, and the results will be presented.