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Synthesis, Crystal Structure and absolute configuration of (+)-O-Phenyl Cyclophosphorodiamidate

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Chinese Journal of Structural Chemistry 2003年第6期22卷 705-709页

作者：何可周正洪李康应赵国锋唐除痴王宏根 State Key Laboratory of Elemento-organic Chemistry Institute of Elemento-organic Chemistry Nankai University Tianjin 300071 China Central Laboratory Nankai University Tianjin 300071China

The title compound, (+)-O-phenyl cyclophosphorodiamidate (C28H33N2O2P, Mr = 460.53), has been synthesized and characterized by 31P NMR, 1H NMR and elemental analysis. X-ray diffraction analysis at 273(2) K indicates that it belongs to orthorhombic system, space group P212121 with a = 11.518(4), b = 13.449(4), c = 16.539(5) ? V = 2562(1) 3, Z = 4, Dc = 1.194 g/cm3, F(000) = 984 and m(MoKa) = 0.134 mm-1. The structure parameters were refined by full-matrix least-squares on F2 to R = 0.0459 and wR = 0.0640. The flack x parameter is 0.03(10), and the absolute configuration of the phosphorus atom in the title compound is S.

关键词： O-phenyl cyclophosphorodiamidate crystal structure absolute configuration

Synthesis and absolute configuration of (2S,3S,3aS,6S,7aR)-2,3-Dihydroxy-2-((R)-1-hydroxy-3-methylbutyl)-3,6-dimethylhexahydrobenzofuran-4(2H)-one

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Chinese Journal of Structural Chemistry 2017年第8期36卷 1276-1282页

作者：李东伟左鸿华胡敏张娇燕陈雷黄年玉 Hubei Key Laboratory of Natural Products Research and Development College of Biological and Pharmaceutical Sciences China Three Gorges University

To investigate the anti-ulcer effect of bisabolangelone reduction derivatives, the sesquiterpene was further proceeded with dihydroxylation reaction. The structure of the target compound was characterized by IR, ESI-MS, 2D NMR and elemental analysis, and its absolute configuration was confirmed with a Flack parameter of 0.08（16） by X-ray crystallography using a Cu radiation source. Compound（3）, C（15）H（26）O5, crystal data： monoclinic system, space group P21, a = 11.467（2）, b = 6.0303（12）, c = 11.711（2） A, β = 99.70（3）°, V = 798.3（3） A3, Z = 2, F（000） = 312, Dc = 1.191 g/cm3, μ = 0.723 mm-1） R = 0.0303 and wR = 0.0797 for 2590 independent reflections（Rint = 0.0164） and 2563 observed ones（I 〉 2σ（I））.

关键词： X-ray diffraction crystal structure absolute configuration bisabolangelone H+/K+ -ATPase inhibitor

Synthesis and absolute configuration of(2R,3S,4Z,6Z)-1,3-bis(benzyloxy)-8-chloro-7-((E)-(2-(2,4-dinitrophenyl)hydrazono)methyl)octa-4,6-dien-2-ol

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Chinese Journal of Structural Chemistry 2020年第10期39卷 1781-1787,1742页

作者： ABDULMAJED OTHMAN Karwan CAI Jin-Jin XIE Rui ZHOU Xin-Ran YAO Hui HUANG Nian-Yu Hubei Key Laboratory of Natural Products Research and Development College of Biological and Pharmaceutical SciencesChina Three Gorges UniversityYichang 443002China Department of Manufacturing and Industrial Engineering Faculty of EngineeringKoya UniversityKoya KOY4545001Kurdistan Region-F.R.Iraq

Lewis acid-catalyzed[1,3]-sigmatropic O→C rearrangement was used to synthesize C-glycosides *** structure of the target compound was characterized by NMR and HR-ESI-MS,and its absolute configuration was *** 8(C(29)H(29)ClN4O7):monoclinic system,space group P212121,a=6.1484(2),b=12.3625(3),c=37.0127(8)A,V=2813.32(13)A3,Z=4,F(000)=1216.0,Dc=1.372 g/cm^3,μ=1.662 mm^1,R=0.0522 and wR=0.1358 for 5611 independent reflections(R(int)=0.0778)and 5169 observed ones(I>2σ(I)).

关键词： X-ray diffraction crystal structure absolute configuration conjugated aliphatic imine cytotoxity

Synthesis and absolute configuration of((2R,3R,6S)-3-Hydroxy-6-(naphthalen-2-ylthio)-3,6-dihydro-2H-pyran-2-yl)methyl Pivalate

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Chinese Journal of Structural Chemistry 2021年第9期40卷 1238-1245,1112页

作者： JIAO Yang ZHANG Jia-Ding WANG Shu-Zhang YAO Hui LIU Ming-Guo HUANG Nian-Yu Hubei Key Laboratory of Natural Products Research and Development Key Laboratory of Functional Yeast(China National Light Industry)College of Biological and Pharmaceutical SciencesChina Three Gorges UniversityTichang 443002China

A stereo-selective palladium-catalyzed one-pot Tsuji-Trost reaction was used to prepare fourβ-thiogalactosides from unsaturated D-galactal and *** structures were characterized by nuclear magnetic resonance spectra and high-resolution electrospray ionization mass *** absolute configuration was confirmed with a Flack parameter of 0.019(15)by X-ray crystallography using a Cu radiation *** 6 a(C_(21)H_(24)O_(4)S):orthorhombic system,space group P2_(1)2_(1)2_(1),a=9.0919(4),b=9.6313(4),c=22.5936(11)A,V=1978.45(15)A^(3),Z=4,F(000)=792,D_(c)=1.250 g/cm^(3),μ=1.636 mm^(-1),R=0.0478 and wR=0.1384 for 3621 independent reflections(Rint=0.0390)and 3326 observed ones(I>2σ(I)).3-(4,5)-Dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide(MTT)cell viability assays indicated that these thiogalactosides showed anti-proliferative activities against human gastric cancer HGC-27 cells with IC_(50)values of 69~88μM.

关键词： X-ray diffraction crystal structure absolute configuration β-thiogalactoside cytotoxity

Determination of the absolute configuration of Rohitukine

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Chinese Chemical Letters 2003年第7期14卷 720-723页

作者： Dong Hui YANG Shao Qing CAI Yu Ying ZHAO Hong LIANG Department of Natural Medicines School of Pharmaceutical SciencesPeking UniversityBeijing 100083

The absolute configuration of rohitukine, isolated from the stem-bark of Dysoxylum binectariferum, was determined to be 5,7-dihydroxy-2-methyl-8-[4-(3S, 4R-3-hydroxy-1-methyl) -piperidinyl]-4H-1-benzopyran-4-one by X-ray crystallographic analysis on the crystal of 4-bromobenzoyl derivatives of rohitukine. At the same time, the modified Mosher method was proved to be unsuitable for determining the absolute configuration of C-3 position in rohitukine.

关键词： Dysoxylum binectariferum absolute configuration rohitukine.

absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells

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Chinese Journal of Natural Medicines 2015年第1期13卷 59-64页

作者： LI Juan FENG Juan LUO Cheng Herman Ho-Yung Sung JIANG Ren-Wang Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization Guangxi Institute of Botany Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research College of Pharmacy Jinan University State Key Laboratory of New Drug Research Shanghai Institute of Materia Medica Chinese Academy of Sciences Department of Chemistry The Hong Kong University of Science and Technology

Podophyllotoxone(1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L-1, respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.

关键词： Podophyllotoxone absolute configuration Prostate cancer Tubulin Molecular docking

Synthesis,Crystal Structure and absolute configuration of (+)-(a-Hydroxybenzyl)phenylphosphinic acid

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Chinese Journal of Structural Chemistry 2002年第4期21卷 368-370页

作者：蔡觉晓周正洪唐除痴王宏根 State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic ChemistryNankai University Tianjin 300071 China Central Laboratory Nankai University Tianjin 300071 China

The title compound (+)-(a-hydroxybenzyl)phenylphosphinic acid (C13H13O3P, Mr = 248.20) has been synthesized and characterized by 31P NMR, 1H NMR and elemental analysis. X-ray diffraction analysis at 293(2) K indicates that the compound belongs to monoclinic system, space group C2 with cell parameters: a = 23.560(8), b = 6.947(2), c = 7.854(3) ? b = 91.273(6)? V = 1285.2(7) 3, Z = 4, Dc = 1.283 g/cm3, F(000) = 520 and m(MoKa) = 0.207 mm-1. The number of independent reflections amounts to 1991, of which 1507 are observed reflections. The crystal structure has been determined by direct methods (SHELXL-97). The structure parameters are refined by full-matrix least-squares on F2 to R = 0.0437 and wR = 0.0893. The flack x parameter is 0.0001. The absolute configuration of the a-carbon in the title compound is S.

关键词： a-hydroxyphosphinic acid (+)-(a-hydroxybenzyl)phenylphosphinic acid crystal structure absolute configuration

The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the absolute configuration of Fusariumin A from the Fungus Fusarium sp.

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Natural Products and Bioprospecting 2016年第1期6卷 41-48页

作者： Liang-Yan Liu Han Sun Christian Griesinger Ji-Kai Liu College of Agronomy and Biotechnology Yunnan Agricultural UniversityKunming 650201China Department of NMR-based Structural Biology Max-Planck-Institute of Biophysical ChemistryAm Fassberg 1137077 Leibniz-Institut für Molekulare Pharmakologie 13125 BerlinGermany School of Pharmaceutical Sciences South-Central University for NationalitiesWuhan 430074China

A new alkylpyrrole derivative,fusariumin A(1),was isolated from the culture broth of the fungus Fusarium *** absolute configuration of fuasiumin A has been established as(2'R,3'R)using a combination of RDC(residual dipolar coupling)-based NMR and DFT-supported chiroptical *** is worth to note that in this study without the aid of the RDC analysis,an unambiguous determination of configuration and conformation was not feasible due to the excessive conformational possibilities of this open-chain compound.

关键词： NMR Residual dipolar coupling Relative configuration absolute configuration Chiroptics

Methods for determination of absolute configuration of monosaccharides

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Chinese Herbal Medicines 2018年第1期10卷 14-22页

作者： nan zhang wei-xing huang gui-yang xia mahmood brobbey oppong li-qing ding pan li feng qiu school of chinese materia medica tianjin university of traditional chinese medicinetianjin 300193china tianjin state key laboratory of modern chinese medicine tianjin university of traditional chinese medicinetianjin 300193china

Monosaccharides are one of the most important structural components of biomolecules, such as polysac- charides, nucleic acids, glycolipids and glycoproteins. In structural analysis of polysaccharides and gly- coconjugates, the absolute configurations （D or L） of the constituent monosaccharides are usually deter- mined by measurement of the optical rotation, CD spectra or characteristic chromatographic retention behavior. However, each method has its unique advantages and limitations which should be considered while using them. In this review, an overview of the different methods for the determination of absolute configuration of monosaccharides and their underlying principles are summarized to serve as a reference for researchers.

关键词： absolute configuration CD chemical derivatization - chromatography monosaccharides optical rotation