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Strategies for constructing seven-membered rings:Applications in natural product synthesis

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Chinese Chemical Letters 2024年第6期35卷 53-70页

作者： peng Chen Lijuan Liang yufei Zhu Zhimin Xing Zhenhua Jia Teck-peng loh College of Advanced Interdisciplinary Science and Technology Henan University of TechnologyZhengzhou 450001China Division of Chemistry and Biological Chemistry School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Nanjing Tech UniversityNanjing 211816China State Key Laboratory of Applied Organic Chemistry Department of ChemistryLanzhou UniversityLanzhou 730000China

The seven-membered ring motifs are found in bioactive pharmaceuticals and a wide range of natural products,including alkaloids and terpenoids,which hold significant importance in synthetic chemistry and has garnered considerable attention from both academia and industry.Despite the challenges faced in the past decade,the total synthesis of natural products incorporating the non-aromatic cycloheptane skeletons remains a compelling pursuit.Recently,numerous elegant strategies for constructing the sevenmembered ring system have been successfully developed.This review focuses on the recent advancements in this field from 2017 to April 2023,highlighting key transformations utilized to construct the non-aromatic cycloheptane core structures and serves as a valuable guide for synthetic chemists engaged in the total synthesis of natural products containing seven-membered ring motifs.

关键词： Seven-membered rings Total synthesis Natural products Synthetic strategy Cycloheptane

Carboxypeptidase E (NF-α1):a new trophic factor in neuroprotection

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Neuroscience Bulletin 2014年第4期30卷 692-696页

作者： yong Cheng Niamh X.Cawley y.peng loh Section on Cellular Neurobiology Program on Developmental NeuroscienceEunice Kennedy Shriver National Institute of Child Health and Human DevelopmentNational Institutes of Health BethesdaMD 20892USA

Carboxypeptidase E （CPE） is a prohormone-processing enzyme and sorting receptor that functions intracellularly. However, recent studies have demonstrated that CPE acts as atrophic factor extracellularly to up-regulate the expression of a pro-survival gene. This mini-review summarizes the roles of CPE in neuroprotection and the implications for neurodegenerative diseases.

关键词： carboxypeptidase E NF-α1 neuroprotection stress neurodegenerative disease

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三芳基碳正离子在有机合成中的应用

有机化学 2024年第2期44卷 421-437页

作者：李路瑶贺忠文张振国贾振华罗德平河南工业大学前沿交叉科学与技术学院郑州450001 南洋理工大学物理与数学科学学院化学与生物化学系新加坡637371

三芳基碳正离子作为一种优异的路易斯酸,其最低空分子轨道(LUMO)轨道能级较低,易接受一对电子,被广泛应用于合成转化中,是重要的试剂和催化剂.近年来,三芳基碳正离子在有机合成中主要被用作催化剂、预催化剂、共催化剂和添加剂.此外,三... 详细信息

三芳基碳正离子作为一种优异的路易斯酸,其最低空分子轨道(LUMO)轨道能级较低,易接受一对电子,被广泛应用于合成转化中,是重要的试剂和催化剂.近年来,三芳基碳正离子在有机合成中主要被用作催化剂、预催化剂、共催化剂和添加剂.此外,三芳基碳正离子作为关键中间体,可以成功应用于四芳基甲烷的合成.综述了近年来三芳基碳正离子在有机合成中的应用进展,并总结了三芳基碳正离子在有机合成中的多种功能作用,希望引起广泛的关注.

关键词：三芳基碳正离子催化剂有机合成无金属

Development of catalyst-free carbon-sulfur bond formation reactions under aqueous media and their applications

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Green Synthesis and Catalysis

Green Synthesis and Catalysis 2022年第4期3卷 309-316页

作者： Min Sun Kang Joycelyn yi Xin Khoo Zhenhua Jia Teck-peng loh Division of Chemistry and Biological Chemistry School of ChemistryChemical Engineering and Biotechnology(CCEB)Nanyang Technological UniversitySingapore 637371Singapore Henan University of Technology 100 Lianhua StZhongyuan DistrictZhengzhou 450001China

Methods for the carbon-sulfur bond formation under catalyst-free,aqueous conditions are extremely useful in organic synthesis and chemical biology.Our laboratory has developed methodologies to construct carbon-thiol bonds,carbon-sulfinic acid bonds,and carbon-disulfide bonds and such methodologies have been widely adopted by other research groups over multidisciplinary fields.In this article,our work on C-S bond formation in an aqueous solvent and its corresponding applications is summarized.

关键词： Green synthesis Biocompatible Water-based reaction Biologics C-S bond

Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes

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Chinese Journal of Chemistry 2019年第10期37卷 1036-1040页

作者： Shengjin Song Huan Liu Lu Wang Chuan Zhu Teck-peng loh Chao Feng Department of Chemistry University of Science and Technology of ChinaHefeiAnhui 230026China Institute of Advanced Synthesis School of Chemistry and Molecular EngineeringJiangsu National Synergetic Innovation Center for Advanced MaterialsNanjing Tech UniversityNanjingJiangsu 211816China Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological University637371Singapore

Herein,we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)-C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides.By merging Rh(Ⅲ)-catalyzed C(sp2)-H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene,an efficient defluorinative vinylation reaction is uncovered,which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions.Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.

关键词： diene catalyzed fluorine

Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Copper-Catalyzed Cyclization of Alkenes

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Chinese Journal of Chemistry 2016年第11期34卷 1076-1080页

作者： Sai-Hu Cai Bing-Chao Da Jia-Hui Zhou yun-He Xu Teck-peng loh Department of Chemistry University of Science and Technology of China Hefei Anhui 230026 China DiVision of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 637371 Singapore

为用铜催化剂的 cis-2,5-disubstituted pyrrolidines 的 stereoselective 合成的有效方法论被开发。相应 cis-2,5-disubstituted pyrrolidines 能作为溶剂作为 ligand 和 1-methyl-2-pyrrolidinone 面对 4,4 ′-di-tert-butyl-2,2′-bi... 详细信息

关键词：立体选择性合成 2-吡咯烷酮铜催化剂二取代顺式环化反应烯烃合成方法

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

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Chinese Chemical Letters 2021年第4期32卷 1411-1414页

作者： Rui-Hua Liu Qi-Chao Shan ya Gao Teck-peng loh Xu-Hong Hu Institute of Advanced Synthesis School of Chemistry and Molecular EngineeringNanjing Tech UniversityNanjing 211816China Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological UniversitySingapore 637371Singapore

Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium ylides.The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives.The synthetic utility of the resultant tetrasubstituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.

关键词： Enamides Sulfoxonium ylides Oxazolines Silver catalysis Heteroannulation

Engineering immunosuppressive drug-resistant armored(IDRA)SARS-CoV-2 T cells for cell therapy

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Cellular & Molecular Immunology 2023年第11期20卷 1300-1312页

作者： Qi Chen Adeline Chia Shou Kit Hang Amy Lim Wee Kun Koh yanchun peng Fei Gao Jili Chen Zack Ho Lu-En Wai Kamini Kunasegaran Anthony Tanoto Tan Nina Le Bert Chiew yee loh yun Shan Goh Laurent Renia Tao Dong Anantharaman Vathsala Antonio Bertoletti Emerging Infectious Disease Program Duke-NUS Medical SchoolSingaporeSingapore National University Centre for Organ Transplantation National University HospitalSingaporeSingapore MRC Human Immunology Unit MRC Weatherall Institute of Molecular MedicineRadcliffe Department of MedicineUniversity of OxfordOxfordUK Lion TCR Pte Ltd SingaporeSingapore A*STAR ID labs Agency for ScienceTechnology and ResearchSingaporeSingapore Lee Kong Chian School of Medicine Nanyang Technological UniversitySingaporeSingapore Department of Medicine Yong Loo Lin School of MedicineNational University of SingaporeSingaporeSingapore Singapore Immunology Network A*STARSingaporeSingapore

Solid organ transplant(SOT)recipients receive immunosuppressive drugs(ISDs)and are susceptible to developing severe COVID-19.Here,we analyze the Spike-specific T-cell response after 3 doses of mRNA vaccine in a group of SOT patients(n=136)treated with different ISDs.We demonstrate that a combination of a calcineurin inhibitor(CNI),mycophenolate mofetil(MMF),and prednisone(Pred)treatment regimen strongly suppressed the mRNA vaccine-induced Spike-specific cellular response.Such defects have clinical consequences because the magnitude of vaccine-induced Spike-specific T cells was directly proportional to the ability of SOT patients to rapidly clear SARS-CoV-2 after breakthrough infection.To then compensate for the T-cell defects induced by immunosuppressive treatment and to develop an alternative therapeutic strategy for SOT patients,we describe production of 6 distinct SARS-CoV-2 epitope-specific ISD-resistant T-cell receptor(TCR)-T cells engineered using the mRNA electroporation method with reactivity minimally affected by mutations occurring in Beta,Delta,Gamma,and Omicron variants.This strategy with transient expression characteristics marks an improvement in the immunotherapeutic field and provides an attractive and novel therapeutic possibility for immunosuppressed COVID-19 patients.

关键词： T cell therapy Transplantation SARS-CoV-2 Immunosuppressive drug resistant T cells

The novel C-terminal Chromogranin A-derived serpinin and pyroglutaminated serpinin act as cardiacβ-adrenergic agonists

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The novel C-terminal Chromogranin A-derived serpinin and pyr...