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Journal of Pharmaceutical Analysis 2017年第5期7卷 303-308页

作者： Xiaoxiao Zhang Lei Gao Zunjian Zhang Yuan Tian Key Laboratory of Drug Quality Control & Pharmacovigilance (China Pharmaceutical University) Ministry of Education State Key Laboratory of Natural Medicine China Pharmaceutical University

A high-performance liquid chromatography coupled with mass spectrometry(HPLC–MS) method was established for the separation and determination of acetyl-glutamine enantiomers(acetylL-glutamine and acetylD-glutamine) simultaneously. Baseline separation was achieved on Chiralpak AD-H column(250 mm ×4.6 mm, 5 μm). n-Hexane(containing 0.1% acetic acid) and ethanol(75:25, v/v) were used as mobile phase at a flow rate of 0.6 m L/min. The detection was operated in the negative ion mode with an ESI source. [M-H]-m/z187.0540 for enantiomers and [M-H]-m/z 179.0240 for aspirin(IS) were selected as detecting ions. The linear range of the calibration curve for each enantiomer was 0.05–40 μg/m L. The precision of this method at concentrations of 0.5–20 μg/m L was within 7.23%, and the accuracy was 99.81%–107.81%. The precision at LOQ(0.05 μg/m L) was between 16.28% and 17.56%, which was poor than that at QC levels. The average extraction recovery was higher than 85% for both enantiomers at QC levels. The pharmacokinetics of enantiomers was found to be stereoselective. There was not chiral inversion in vivo or in vitro between enantiomers.

关键词： HPLC–MS Acetyl-glutamine enantiomers separation Pharmacokinetics Chiral inversion

Discovery of Natural Co-occurring enantiomers of Monoterpenoid Indole Alkaloids

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Chinese Journal of Chemistry 2021年第4期39卷 866-872页

作者： Yang Yu Mei-Fen Bao Xiang-Hai Cai State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan650201 China

Main observation and conclusion Two new pairs of monoterpenoid indole alkaloids(MIAs)enantiomers as well as their new congeners were isolated from stems of Tabernaemontana bovina Lour.(Apocynaceae).Their structures were elucidated by spectroscopic analyses and confirmed by X-ray diffractions and computational calculations.Tabovine A,tabovine B and tabovines C-D possessed unprecedented 6/5/5/6/6,6/5/5/6/5 and 6/5/6/6/6 ring systems,respectively.It is the first time to report co-occurring enantiomers of MIAs.Additionally,the explanation concerning biogenesis of MIAs was provided.The findings would open a new window where we could disclose more diverse MIAs.

关键词： Monoterpenoid indole alkaloid enantiomers Tabovines A-D Structure elucidation Extraction and isolation

Synthesis,crystal structures and characterization of a pair of Tb~Ⅲ-based enantiomers

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Journal of Rare Earths 2011年第1期29卷 28-31页

作者：方少明牛晓霞和来福户敏周立明高丽君李郤里 Henan Provincial Key Laboratory of Surface and Interface Science School of Materials and Chemical EngineeringZhengzhou University of Light Industry

A pair of novel Tb^III-based enantiomers, [Tb（dbm）·Lss] （1） and [Tb（dbm）3.LRR] （2）（where Lss=（＋）-4,5-pinene bipyridine, LRR= （-）-4,5-pinene bipyridine, dbm=dibenzoylmethanate）, were synthesized and characterized based on single crystal X-ray diffi＇action, elemental analysis, FT-IR, TG and CD spectra. X-ray diffraction analysis showed that both the complexes crystallized in monoclinic crystal system with P21 chiral space group. The Tb^III ion was eight-coordinated by six O atoms of three dbm ligands and two N atoms fi-om one chiral ligand Lss or LRR. The CD spectra revealed that complexes 1 and 2 were enantiomers. Thermogravimetric analysis results indicated that 1 and 2 were thermally stable up to 246 ℃.

关键词： enantiomers chirality rare earths terbium complex

Stereoselective HPLC Assay of TJ0711 enantiomers by Precolumn Derivatization with GITC Using UV Detection and Its Application in Pharmacokinetics in Rats

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Journal of Huazhong University of Science and Technology(Medical Sciences) 2009年第4期29卷 427-430页

作者：孙淑萍斯陆勤范昭泽裘军李高 School of Pharmacy Tongji Medical CollegeHuazhong University of Science and Technology

This investigation describes a new precise, sensitive and accurate stereoselective RP-HPLC method for determination of the enantiomers of a novel α- and β-receptor blocking agent, 1-[4-（2-methoxyethyl） phenoxy]-3-[[2-（2- methoxyphenoxy） ethyl]amino]-2-propanol （T J0711）, in rat plasma. GITC was used for precolunm derivatization of T J0711 enantiomers. Enantiomeric resolution was achieved on a Eurospher-100 C18 column （250 mm×4.6 mm ID, 5-μm particle size）, with UV detection at 255 nm, and the mobile phase consisted of acetonitrile and water （58：42, v/v） containing 0.02% glacial acetic acid （v/v）. Using the chromatographic conditions described, T J0711 enantiomers were well resolved with mean retention time of 10.2 and 11.5 min, respectively. Linear response （r〉0.999） was observed over the range of 0.125-12.5 μg/mL of TJ0711 hydrochloride enantiomers. The mean relative standard deviation （RSD%） of the results of within-day precision was ≤ 10%. The proposed method was found to be suitable and accurate for the quantitative determination of T J0711 enantiomers in rat plasma, and it can be used in pharmacokinetic studies.

关键词： TJ0711 stereoselective HPLC enantiomers GITC pharmacokinetics

enantiomers of Ohmefentanyl and Its Analgesic Activity

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Chinese Science Bulletin 1994年第23期39卷 2004-2008页

作者：王智贤朱友成陈新建嵇汝运 Shanghai Institute of Materia Medico Academia Sinica Shanghai 200031 PRC

Since the existence of multiple opioid receptors was first proposed by Martin,this concept was subsequently substantiated by the pharmacological tests and receptor binding assays.Now three subclasses of opioid recepto... 详细信息

关键词： ohmefentanyl enantiomers stereoselective synthesis analgesic activity.

Resolution of α-cyclohexyl-mandelic acid enantiomers by two-phase (O/W) recognition chiral extraction

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Science China Chemistry 2007年第6期50卷 764-769页

作者： TANG KeWen1,2, ZHANG GuoLi2, HUANG KeLong2, LI Yuanjian3 & YI JianMin1,2 1 Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414000, China 2 College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China 3 College of Pharmaceutical Science, Central South University, Changsha 410078, China Department of Chemistry and Chemical Engineering Hunan Institute of Science and Technology Yueyang China College of Chemistry and Chemical Engineering Central South University Changsha China College of Pharmaceutical Science Central South University Changsha China

This paper presents a new chiral separation technology: two-phase (O/W) recognition chiral extraction. Distribution behavior of α-cyclohexyl-mandelic acid enantiomers was studied in the extraction system with D(L)-isobutyl tartrate in 1,2-dichloroethane organic phase and β-CD derivatives in aqueous phase, and the influence of the kind and concentration of extractant and pH on extraction performance was investigated. The experimental results indicate that two-phase (O/W) recognition chiral extraction is of strong chiral separation ability. HP-β-CD, HE-β-CD and Me-β-CD have higher recognition ability for S-CHMA than that for R-CHMA, among which HP-β-CD has the strongest ability; whereas, D-isobutyl tartrate has reversed recognition ability for them. In the extraction system containing HP-β-CD and D-isobutyl tartrate, e.e.% of S-CHMA in aqueous phase reached 27.6% by one stage extraction, and the distribution ratio for R-CHMA(kR) and for S-CHMA(kS) and separation factor (α) are 2.44, 0.89 and 2.49, respectively. Meanwhile, pH and concentration of extractant have great effects on chiral separation ability. Two-phase (O/W) recognition chiral extraction has great significance for preparative separation of racemic compounds.

关键词： two-phase(W/O) recognition, chiral extraction, α-cyclohexyl-mandelic acid enantiomers

High performance liquid chromatographic separation of clausenamide enantiomers with chiral-AGP stationary phase

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Chinese Chemical Letters 2010年第7期21卷 860-863页

作者： Yan Wang Qing Qiang Yao Mu Zou Wang Institute of Materia Medica Chinese Academy of Medical Sciences & Peking Union Medical CollegeBeijing 100050China Institute of Materia Medica Shandong Academy of Medical ScienceJinan 250062China

A method of high performance liquid chromatographic separation of clausenamide enantiomers with chiral-AGP（α_1-acid glycoprotein） stationary phases has been established.The absolute configurations of（-）clausenamide and（＋）clausenamide are 3S, 4R,5R,6S and 3R,4S,5S,6R,respectively.The present method has been used to analyze the（-）clausenamide and（＋）clausenamide and its analogues such as the major metabolite and synthetic derivatives of clausenamide.

关键词： enantiomers （-）Clausenamide （＋）Clausenamide Chiral-AGP HPLC

Enantioselective extraction of terbutaline enantiomers by lipophilic tartaric acid

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Journal of Central South University of Technology 2003年第1期10卷 44-48页

作者： TANG Ke-wen(唐课文) ZHOU Chun-shan(周春山) College of Chemistry and Chemical Engineering Central South University Changsha 410083 China Department of Chemistry and Chemical Engineering Yueyang Normal University Yueyang 414000 China College of Chemistry and Chemical Engineering Central South University Changsha 410083 China

Distribution behavior of terbutaline enantiomers was examined in the aqueous and organic solvent of a two-phase system containing L-dibenzoyltartaric acid and lipophilic phase transfer reagent of Na-tetraphenylborate. The influences of pH, organic solvents, concentrations of Na-tetraphenylborate and L-dibenzoyltartaric acid on the partition coefficients and enantioselectivity of terbutaline enantiomers, were investigated. The results show that tetraphenylborate lipophilic anion and terbutaline enantiomers form two lipophilic salt complexes , which facilitates the solubility of the enantiomers in the organic phase. L-dibenzoyltartaric acid forms more stable complexes with enantiomer Ⅱ than with enantiomer I . Enantioselectivity and partition coefficient increase with the addition of the length of alkyl chain of alcohols. pH and concentrations of lipophilic anion and L-dibenzoyltartaric acid influence them obviously and differently.

关键词： L-dibenzoyltartaric acid terbutaline enantiomers chiral extraction

The profiles of chiral pesticides in peri-urban areas near Yangtze River: Enantioselective distribution characteristics and correlations with surface sediments

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Journal of Environmental Sciences 2022年第11期34卷 199-210页

作者： Wenjun Zhang Tingting Li Jiayi Tang Xiaoli Liu Yuhang Liu Xiao Zhong Key Laboratory of Integrated Regulation and Resources Development on Shallow Lakes of Ministry of Education College of EnvironmentHohai UniversityNanjing 210098China

Chiral pesticides account for 30% of pesticides. Pesticides are inevitably leached into the groundwater by runoff. At the watershed level, the distribution characteristics of enantiomers in sediments collected from the river network of an agricultural area near the middle and lower reaches of the Yangtze River were tested, and their potential correlations with the physicochemical properties and microbial communities of the sediments were analyzed. The sediment pollution was serious at sites 8 and 9, with their pollution source possibly being agricultural or industrial sewage. Moreover, there were higher cumulative contents of pesticide residues at sites 4, 8, and 9. Specifically, Cycloxaprid was the most detected chiral pesticide in the study area, followed by Dinotefuran and Diclofop-methyl. Additionally,Ethiprole and Difenoconazole had strong enantioselectivity in the study area. Interestingly,the enantiomers of some chiral pesticides, such as Tebuconazole, had completely different distributions at different sites. Pearson correlation analysis showed that sediment catalase and microbial biomass carbon were important factors for enantioselectivity of chiral pesticides. The effect of sediment physicochemical properties on enantioselective distribution was achieved by influencing the microorganisms in the sediment. Furthermore, the enantioselective distribution of Tebuconazole was closely related to the genus Arenimonas.Overall, the enantioselective distribution of most of the chiral pesticides was positively correlated with the prokaryotic microbial community. This study provides empirical support for agricultural non-point source pollution caused by chiral pesticides, and also lays a research foundation for exploring the factors that affect the fate of chiral pesticides in the environment.

关键词： Non-point source pollution enantiomers Redundancy analysis Sediment enzymes Microbial community

Influence of CYP2D610B genotype on pharmacokinetics of propafenone enantiomers in Chinese subjects

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Acta Pharmacologica Sinica 2003年第12期 103-106页

作者： CHEN Bing CAI Wei-Min Department of Clinical Pharmacology, Jinling Hospital, Nanjing 210002, China

AIM: To study the relationship between genotype of CYP2D6* 10B and pharmacokinetics of propafenone enantiomers. METHODS: Genotype of 17 healthy Chinese HAN subjects was determined by an allele specific amplification method. The blood samples (0-15 h) of the subjects were taken after oral administration of a single dose (400 mg) of propafenone hydrochloride. Concentrations of propafenone enantiomers in plasma were measured by a reverse-phase HPLC with precolumn derivatization. RESULTS: Seventeen subjects characterized for CYP2D6* 10B genotype included (*1/*1) (n=4), (*1/*10) (n=5) and (*10/*10) (n=8). The metabolic ratios (lg MR) of the three genotypes were-2.68±0.23, -2.2±0.7, and -1.1±0.5, respectively. The AUC of the three groups were (1534±334), (1891±793), (3171±1075) μg·h·L-1for S-enantiomer and (1136±345), (1467±817), (2277±745) μg·h·L-1for R-enantiomer, respectively. The AUC of propafenone enantiomers in *10/*10 is about 1.5-2 times of that of *1/*10 group or *1/*1 group, a

关键词： propafenone pharmacokinetics CYP2D6~* 10B genotype phenotype enantiomers