• 한국자기공명학회논문지
• /
• 제27권4호
• /
• pp.35-41
• /
• 2023

From a marine sponge Dysidea species, four new furanosesquiterterpenoids were isolated and characterized. Their structural elucidation was achieved through an extensive analysis employing NMR, MS data, and DFT method. Notably, all compounds shared as identical molecular formula. Compound 2 was identified as a derivative of compound 1, while compounds 3 and 4 exhibited an identical planar structure. Determination of the configurations of chiral centers in compounds 1 and 2 involved a comparative analysis between measured and calculated ECD spectra, along with the application of DP4+ probability analysis. Distinctly, the configurations of isomers 3 and 4 were established by scrutinizing proton chemical shifts based on the NOE correlation.

• Biotechnology and Bioprocess Engineering:BBE
• /
• 제9권4호
• /
• pp.285-291
• /
• 2004

A simulated moving bed (SMB) chromatography system is a powerful tool for preparative scale separation, which can be applied to the separation of chiral compound. We have de-signed our own lab-scale SMB chromatography using 5 HPLC pumps, 6 stainless steel columns and 4 multi-position valves, to separate a racemic mixture of ketoprofen in to its enantiomers. Our design has the characteristics of the low cost for assembly for the SMB chromatography and easy repair of the unit, which differs from the designs suggested by other investigators. It is possible for the flow path through each column to be independently changed by computer control, using 4 multi-position rotary valves and 5 HPLC solvent delivery pumps. In order to prove the operability of our SMB system, attempts were made to separate the (S)-ketoprofen enantiomer from a ketoprofen racemic mixture. The operating parameters of the SMB chromatography were calculated for ketoprofen separation from a batch chromatography experiment as well as by the triangle theory. With a feed concentration of 1 mg/mL, (S)-ketoprofen was obtained with a purity of 96% under the calculated operating conditions.

• Journal of Microbiology and Biotechnology
• /
• 제23권2호
• /
• pp.218-224
• /
• 2013

The aldo-keto reductases catalyze reduction reactions using various aliphatic and aromatic aldehydes/ketones. Most reductases require NADPH exclusively as their cofactors. However, NADPH is much more expensive and unstable than NADH. In this study, we attempted to change the five amino acid residues that interact with the 2'-phosphate group of the adenosine ribose of NADPH. These residues were selected based on a docking model of the YOL151W reductase and were substituted with other amino acids to develop NADH-utilizing enzymes. Ten mutants were constructed by site-directed mutagenesis and expressed in Escherichia coli. Among them, four mutants showed higher reductase activities than wild-type when using the NADH cofactor. Analysis of the kinetic parameters for the wild type and mutants indicated that the $k_{cat}/K_{m}$ value of the Asn9Glu mutant toward NADH increased 3-fold. A docking model was used to show that the carboxyl group of Glu 9 of the mutant formed an additional hydrogen bond with the 2'-hydroxyl group of adenosine ribose. The Asn9Glu mutant was able to produce (R)-ethyl-4-chloro-3-hydroxyl butanoate rapidly when using the NADH regeneration system.

• 분석과학
• /
• 제33권2호
• /
• pp.59-67
• /
• 2020

Nadolol is a β-blocker drug, which effectively manages hypertension and angina pectoris. Its chemical structure allows the formation of four possible stereoisomers. A coupled column high-performance liquid chromatographic (HPLC) system with UV and fluorescence detection was investigated for simultaneously determining four nadolol enantiomers in human plasma. The plasma samples were prepared using a convenient liquid-liquid extraction process and passed through HPLC. Nadolol was initially separated from the endogenous compounds or other impurities in human plasma on a Phenomenex silica column, and its enantiomers were resolved and determined on a Chirapak AD-H column. The developed HPLC method achieved an effective chiral separation and significantly eliminated endogenous compound interference. This optimal HPLC method was validated following FDA guidelines. The results showed good selectivity, linearity, accuracy (90.50 % - 105.27 %), and precision (RSDs < 9.52 %) for each enantiomer. This method was also successfully applied to determine nadolol enantiomers in the plasma samples of a healthy male volunteer (after orally administering 80 mg racemic nadolol), proving its suitability for nadolol stereoselective pharmacokinetic studies.

• 한국자기공명학회논문지
• /
• 제15권2호
• /
• pp.128-136
• /
• 2011

A new sesterterpenoid, phorbaketal derivative, was isolated from the marine sponge Phorbas species. Its planar structures was completely determined from a combination of extensive 1D and 2D NMR experiments and MS data, and also the stereochemistry on the chiral centers were established by the ROESY experiment and the comparison with the $^1H$ and $^{13}C$ chemical shifts of the known phorbaketal compounds. This compound 1 moderately showed cytotoxicity effect against hepatoma cancer HepG2 cell.

• Fisheries and Aquatic Sciences
• /
• 제15권1호
• /
• pp.15-19
• /
• 2012

A new cyclic peptide (six-membered amino acid), gamakamide-E (L-Leu-L-Met (SO)-L-Me-Phe-L-Leu-D-Lys-L-Phe), was isolated as a strongly bitter tasting compound from cultured oysters, Crassostrea gigas. The molecular formula of $C_{43}H_{61}N_7O_8S$ was deduced from high resolution fast atom bombardment mass spectrometry (HR FAB-MS) ($[M+H]^+$ m/z 836.4356 ${\Delta}$= -2.4 mmu). Its unique structure including a hydantoin structure was firstly elucidated by nuclear magnetic resonance (NMR) analysis. Stereochemistries of constituent amino acids were determined by chiral high performanced liquid chromatography analysis of natural and synthesized peptides.

• 한국자기공명학회논문지
• /
• 제12권1호
• /
• pp.33-39
• /
• 2008

Four sesterterpenoids were isolated from AMPK activity-guided fraction of marine sponge Sarcotragus species. Their planar structures were determined from combination of extensive 1D and 2D NMR experiments and MS data, and the configuration at the chiral centers were assigned by comparison with the $^1H$ and $^{13}C$ chemical shifts of the known compounds. Among four compounds, compound 2 was found to be a new sarcotrine derivative. Though not strong, compounds 1-4 moderately showed AMPK activation effect on L6 myoblast cell through Western Blot analysis.

• 대한약학회:학술대회논문집
• /
• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
• /
• pp.179.1-179.1
• /
• 2003

CKD-712, named S-YS49 is a chiral compound derived from higenamine (one component of Aconite spp.) derivatives. To compare the cytotoxicity of CKD-712 between in the absence and in the presence of S9 metabolic activation system, we performed try pan blue dye exclusion assay in Chinese hamster lung (CHL) cell. In CHL cells, the cytotoxicity ($IC_{50}$) of CKD-712 was 92.9 ${\m}g$/$m\ell$ and 186.1 ${\m}g$/$m\ell$ in the absence and presence of S9 metabolic activation, respectively. (omitted)

• Biotechnology and Bioprocess Engineering:BBE
• /
• 제5권1호
• /
• pp.57-60
• /
• 2000

$(R)-\beta-acetylmercaptoisobutyric$ acid (RAM), a chiral compound, is an important intermediate for the chemical synthesis of various antihypertensive and congestive heart failure drugs. Microorganisms capable of converting $(R,S)-\beta-acetylmercaptoisobutyric$ acid ((R,S)-ester) to RAM were screened from soil microorganisms. A strain of Pseudomonas sp. 1001 screened from a soil sample was selected to be the best. Cells showed an activity of 540 U/mL from culture broth and the enzyme was thermostable up to $70^{\circ}C$. This strain could produce RAM asymmetrically from (R,S)-ester.

• 한국결정학회지
• /
• 제11권2호
• /
• pp.95-101
• /
• 2000

Ferroelectric SrBi2Ta2O9 (SBT) thin films of Pt/Ti/SiO2 electrode were fabricated using a sintered SBT target with various Bi2O3 content by rf magnetron sputtering. Good hysteresis loop characteristics were observed in the SBT thin films deposited with 50mol% excess Bi target. SBT thin films crystallized from 650℃ however, good hysteresis loop can be obtained in the film annealed above 700℃. pt/TiO2/SiO2 and Pt/SiO2 electrodes were also used to investigate the Pt electrode dependence of SBT thin films. SBT thin films showed random oriented polycrystalline structure and similar morphology regardless of electrodes with quite different surface morphology. A 0.2㎛ thick SBT film annealed at 750℃ exhibited the remanent polarization (2Pr) of μC/㎠ and coercive voltage(Vc) of 1V at an applied voltage of 5V.