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Electrospray Ionization Mass Spectra of Amino Acid Methyl Ester 5′-Phosphoramidates of 2′,3′-Isopropylideneuridine

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Chemical Research in Chinese Universities 2006年第6期22卷 732-737页

作者： CHEN Wei-zhu GAO yu-xing BAI Yong-gang HAN Da-xiong zhao yu-fen The Key Laboratory for Chemical Biology of Fujian Province Department of Chemistry College of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 P. R. China Key Laboratory for Bioorganic Phosphorus Chemistry of the Ministry of Education Department of Chemistry School of Life Sciences and Engineering Tsinghua University Beijin 100084 P. R. China The Third Institute of Oceanography of the State Oceanic Administration Xiamen 361005 P. R. China

Amino acid methyl ester phosphates were synthesized and determined by using positive-ion mode dectrospmy ionization mass spectrometry（ESIMS） in combination with multistage tandem mass spectrometry. The fragmentation pathways were investigated, and it was observed that most fragment ions contained the phosphoryl group. It was interesting to observe that the fragmentation pathways of the protonated molecule show some differences when compared with those of the sodium ion adduct. The methoxy group of amino acid methyl ester can migrate from the carbonyl group to the phosphoryl group in the sodium ion adduct.

关键词： ESIMS Fragmentation pathway Methoxy group rearrangement Pentacoordinated phosphorus intermediate Amino acid methyl ester 5'-phosphoramidate of nucleoside

Syntheses and Crystal Structures of Two New α-Aminophosphonate Derivatives Containing Thieno[2,3-d]pyrimidine

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Chinese Journal of Structural Chemistry 2015年第6期34卷 879-884页

作者： ZHU Xi-feng GUO Yan-Chun yu Zhi-Ran LIAO Xin-Cheng zhao yu-fen The College of Chemistry and Molecular Engineering The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University Department of Chemistry College of Chemistry and Chemical Engineering The Key Laboratory for Chemical Biology of Fujian Province Xiamen University

Two new a-aminophosphonate derivatives containing thieno[2,3-d]pyrimidine, diethyl（（（6-ethyl-2-methyl-4-oxothieno[2,3-d]pyrimidin-3 （4H）-yl）amino）（4-methoxyphenyl）methyl） phosphonate （1） and diethyl（（4-bromophenyl）（（6-ethyl-2-methyl-4-oxothieno[2,3-d]pyrimidin-3 （4//）-yl）amino）methyl）phosphonate （2）, have been synthesized by a facial phosphorylated reaction, and their structures were characterized by NMR, IR, HRMS and X-ray single-crystal diffraction. Compound 1 （C21H28N3O5PS, Mr = 465.49） belongs to the orthorhombic system, space group P212121, with a = 10.83653（16）, b = 12.04906（19）, c = 18.0061（3） A, V= 2351.06（6） A3, Z= 4, Dc= 1.315 g/cm3, p = 2.177 mm-1, F（000） = 984.0, the final R = 0.0389 and wR = 0.0985 for all data. Compound 2 （C20H25BrN304PS, Mr = 514.37） belongs to the orthorhombic system, space group P212121, with a = 10.9187（5）, b = 11.9522（4）, c = 17.7667（7） A, V= 2318.60（16） A3, Z = 4, Dc= 1.474 g/cm3,μ = 4.175 mm^-1, F（000） = 1056.0, the final R = 0.0367 and wR = 0.0946 for all data.

关键词： thieno[2,3-d]pyrimidine a-aminophosphonate derivatives synthesis crystal structure

Chinese Medicine Meets Conventional Medicine in Targeting COVID-19 Pathophysiology,Complications and Comorbidities

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Chinese Journal of Integrative Medicine 2022年第7期28卷 627-635页

作者： WANG Shan-shan ZENG Xian WANG Ya-li Zhuoma Dongzhi zhao yu-fen CHEN yu-zong Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences Institute of Drug Discovery TechnologyNingbo UniversityNingboZhejiang Province 315211China Department of Biological Medicines&Shanghai Engineering Research Center of Immunotherapeutics Fudan University School of PharmacyShanghai 201203China Bioinformatics and Drug Design Group Department of PharmacyNational University of Singapore117543Singapore Medical College Tibet UniversityLhasa 850011China Department of Chemical Biology College of Chemistry and Chemical Engineeringand The Key Laboratory for Chemical Biology of Fujian ProvinceXiamen UniversityXiamenFujian Province 361005China Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology(Ministry of Education) Department of ChemistryTsinghua UniversityBeijing 102206China

Objective: To investigate how the National Health Commission of China(NHCC)-recommended Chinese medicines(CMs) modulate the major maladjustments of coronavirus disease 2019(COVID-19),particularly the clinically observed complications and comorbidities. Methods: By focusing on the potent targets in common with the conventional medicines, we investigated the mechanisms of 11 NHCC-recommended CMs in the modulation of the major COVID-19 pathophysiology(hyperinflammations, viral replication), complications(pain, headache) and comorbidities(hypertension, obesity, diabetes). The constituent herbs of these CMs and their chemical ingredients were from the Traditional Chinese Medicine Information Database. The experimentally-determined targets and the activity values of the chemical ingredients of these CMs were from the Natural Product Activity and Species Source Database. The approved and clinical trial drugs against these targets were searched from the Therapeutic Target Database and DrugBank Database. Pathways of the targets was obtained from Kyoto Encyclopedia of Genes and Genomes and additional literature search. Results: Overall,9 CMs modulated 6 targets discovered by the COVID-19 target discovery studies, 8 and 11 CMs modulated 8and 6 targets of the approved or clinical trial drugs for the treatment of the major COVID-19 complications and comorbidities, respectively. Conclusion: The coordinated actions of each NHCC-recommended CM against a few targets of the major COVID-19 pathophysiology, complications and comorbidities, partly have common mechanisms with the conventional medicines.

关键词： COVID-19 Chinese medicine target therapeutic mechanism pathophysiology comorbidity

Highly Selective Preparation of 3-and 6-Modified Mannose/Altrose Derivatives

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Chemical Research in Chinese Universities 2006年第3期22卷 339-342页

作者： LIU Xiao-hong XIE Dang CHENG Chang-mei WANG Xia-yu GUO Xiao-qiang zhao yu-fen Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology of Ministry of Education Department of Chemistry Tsinghua University Beijing 100084 P.R. China Institute of Polymer Science and Engineering Xiangtan University Xiangtan 411105 P.R. China

A highly efficient method to get 3-and 6-modified mannose/ahrose derivatives for oligosaccharide synthesis is described. All the compounds were obtained exclusively with the combinations of 3-and/or 6-hydroxyl protect... 详细信息

关键词： Mannose Altrose Selective protection Selective deprotection

Studies on Fragmentation Pathways of N-Ethoxy(phenyl) phosphoryl Amino Acids by Electrospray Ionization Tandem Mass Spectrometry

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Chemical Research in Chinese Universities 2006年第5期22卷 598-601页

作者： CAO Shu-xia LI Hong-wei GUO Yan-chun LIAO Xin-cheng zhao yu-fen The Key Laboratory of Chemical Biology and Organic Chemistry Department of Chemistry Zhengzhou University Zhengzhou 450052 P. R. China The Key Laboratory for Bioorganic Phosphorus Chemistry and Chemical Biology Ministry of Education Department of Chemistry School of Life Sciences and Engineering Tsinghua University Beijing 100084 P. R. China

The positive and negative ESI-MS/MS spectra of N-ethoxy（phenyl） phosphoryl amino acids（EPP-AA） were investigated by electrospray ionization（ESI） ion trap mass spectrometry. The fragmentation pathways of [ M ＋ Na]^＋ and [ M - H]^- ions are proposed and rationalized. The observation may have some potential applications in the interpretation of the MS/MS spectra of novel N-phosphoryl compounds. The complexity of MS/MS spectra of EPP-AA [ M ＋ Na]^＋ ions is decreased compared with that of N-dialkyloxyphosphoryl amino acid. Therefore, the new phosphonamidate method may be considered one of the superior methods that can be used in sequencing peptides and proteins extensively.

关键词： N-Ethoxy(phenyl) phosphoryl amino acid Electrospray ionization ion trap mass spectrometry Tandem mass spectrometry

Structure and Quantum Chemistry Study on Hexaacetyl D-Mannose Hydrazine

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Chinese Journal of Structural Chemistry 2007年第8期26卷 911-916页

作者： CAO Rui LIU Xiao-Hong CHENG Chang-Mei WANG Ru-Ji zhao yu-fen WANG Lai-Xi Key Laboratory of Bioorganic Phosphorus Chemistry ＆ Chemical Biology （Ministry of Education） Department of Chemistry Tsinghua University Beijing 100084 China Institute of Human Virology University of Maryland Biotechnology Institute University of Maryland USA

Hexaacetyl D-mannose hydrazine is one type of important intermediates in saccharide chemistry. In this paper, its single crystal was obtained and furthermore, X-ray diffraction and quantum chemistry calculation were performed. It belongs to orthorhombic system, space group P212121, with a=16.267（3）, b=19.263（3）, c=7.1948（12）A, Mr=446.41, Dc=1.315 g/cm^3, V=2254.5（6）A^3 and Z=4. Meanwhile, the experimental results also provide information for designing a kind of molecular switch based on the mannose nitrogenous derivatives.

关键词： hexaaeetyl D-mannose hydrazine crystal structure calculation of quantum chemistry molecular switch

Influence of Basicity on the Formation of Cluster Ions/Adduct Ions for Organic Ammonium Halides by Positive Secondary Ion Mass Spectrometry

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Chemical Research in Chinese Universities 1997年第4期13卷 93-97页

作者： FU Hua CHEN Xin LI zhao long zhao yu fen WANG Jing zun XIAO Hong zhan WU Yi Bioorganic Phosphorus Chemistry Laboratory Department of ChemistryTsinghua UniversityBeijing100084 Beijing Institute of Microchemistry Beijing100091

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关键词： Positive secondary ion mass spectrometry(PSIMS) Organic ammonium halide Basicity Cluster ion /Adduct ion

A New Intermolecular Phosphoryl Transfer between Serine and Histidine Residues

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有机化学 2004年第Z1期24卷 349-350页

作者： SU,yu-Qian NIU,Ming-yu CAO,Shu-Xia ZHANG,Jian-Chen QU,Ling-Bo LIAO,Xin-Cheng zhao,yu-fen The Key Laboratory of Chemical Biology Department of Chemistry Zhengzhou University Zhengzhou 450052

Phosphoryl transfer constitutes one of the most important reactions in functionalized molecules, bioorganic chemistry and biochemistry.[1] The transformations are involved in diverse processes, such as activated state change of phosphorus, DNA/RNA synthesis, energy metabolism and signal transduction. So, phosphoryl transfer reaction which can be performed by either intramolecular or intermolecular phosphorylation and dephosphorylation mechanism has been investigated by many scientists in wide fields.……

关键词： signal transduction state change

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磷氰酸阴离子在化学合成中的应用

化学试剂 2024年第9期46卷 66-80页

作者：童梦楠罗永安管小军吴翊乐胡英赵玉芬浙江药科职业大学药学院浙江宁波315100 宁波大学新药技术研究院天体化学与空间生命-钱学森空间科学协同研究中心浙江宁波315211

磷氰酸阴离子(OCP-)作为氰酸盐离子(OCN-)的等电体,两者在反应活性上存在明显差异。自1992年OCP-结构首次确认以来,如何安全、简便、经济、环保地合成稳定的OCP-化合物并对该物质及其衍生物的活性进行研究一度成为磷化学研究的热点。综... 详细信息

磷氰酸阴离子(OCP-)作为氰酸盐离子(OCN-)的等电体,两者在反应活性上存在明显差异。自1992年OCP-结构首次确认以来,如何安全、简便、经济、环保地合成稳定的OCP-化合物并对该物质及其衍生物的活性进行研究一度成为磷化学研究的热点。综述了OCP-的合成研究进展以及其在金属有机化学、小分子活化等领域中的反应活性研究,旨在为推动OCP-参与的相关活性研究,为其在小分子气体转化应用、催化剂设计、材料化学等多领域的研究做出贡献。同时,由于OCP-可以作为合成子用于构筑多种多样的含磷有机化合物,因此可以为药物研发领域提供新的候选分子。

关键词：磷氰酸阴离子主族元素化学磷化学杂环小分子活化