Cu-Catalyzed Click Reaction in Carbohydrate Chemistry
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- 作者：Vinod K. Tiwari ; Bhuwan B. Mishra ; Kunj B. Mishra ; Nidhi Mishra ; Anoop S. Singh ; Xi Chen
- 刊名：Chemical Reviews
- 出版年：2016
- 出版时间：March 9, 2016
- 年：2016
- 卷：116
- 期：5
- 页码：3086-3240
- 全文大小：11251K
- 年卷期：Vinod K. Tiwari
, born in Bihar, India, in 1976, has been an Assistant Professor of Organic Chemistry at Banaras Hindu University (BHU) since 2005. After obtaining his M.Sc. (1998) from BHU, he worked on the development of carbohydrate-based molecules of chemotherapeutic potential at the Central Drug Research Institute, Lucknow, India (with Dr. R. P. Tripathi as his mentor), starting in 2000 and obtained his Ph.D. degree from Jawaharlal Nehru University, New Delhi, in 2004. He was offered a Lecturership at Bundelkhand University, Jhansi, India (2004–2005), before starting his independent research career at BHU (2005 to present). He worked on the chemoenzymatic synthesis of complex carbohydrate-containing molecules as a Postdoctoral Fellow (with Prof. Xi Chen as his mentor) at the University of California—Davis, United States (2007), and subsequently on the novel intramolecular glycosidic bond formation methodology as a Visiting Scientist (with Prof. Richard R. Schmidt as his mentor) at Universität Konstanz, Germany. He has had interest in the benzotriazole methodology since 2005 through his postdoctoral research with Prof. Alan R. Katritzky at the University of Florida, United States. His present research interest focuses on different aspects of carbohydrate chemistry and organic synthesis. He has supervised eight Ph.D. students and completed three major research projects (Department of Science & Technology (DST), University Grants Commission (UGC), and Council of Scientific & Industrial Research (CSIR)). He has delivered numerous invited lectures at different institutes in India and abroad (over 70) and serves on the editorial board of several journals, including Trends in Carbohydrate Research, the International Journal of Carbohydrate Chemistry, and Biochemical Compounds. He edited the popular book Opportunity, Challenge and Scope of Natural Products in Medicinal Chemistry and recently assisted with editing the ARKIVOC issue in honor of Prof. Richard R. Schmidt. He serves as a Joint Secretary for the Association of Carbohydrate Chemists & Technologists, India (ACCTI) (2014 to present). Dr. Tiwari has significantly contributed over 100 peer-reviewed publications (h-index = 26), including several patents and invited book chapters. He has received many prestigious awards and medals, such as the Dr. D. S. Bhakuni Award, Indian Chemical Society (2004), the Young Investigator Prize (2004), the Most Cited Paper Award (in 2006 from Elsevier and in 2015 from Bentham Science), the Dr. Arvind Kumar Memorial Award, Indian Council of Chemists (2010), the Uttar Pradesh (UP) Council of Science & Technology (CST) Young Scientist Award (2010), the Prof. R. C. Shah Memorial Award, The Indian Science Congress Association (2011), the Dr. Ghanshyam Srivastava Memorial Award, Indian Chemical Society (2012), the 1st Tatva Scientist of the Year-2014, International Academy of Physical Sciences, the Young Scientist Award-2012, Chemical Research Society of India (CRSI), the 1st Dr. H. C. Srivastava Memorial Award, ACCTI (2012), the Professor A. S. R. Anjaneyulu 60th Birthday Commemoration Award-2014, Prof. N. Roy Award for Excellence in Synthetic Carbohydrate Chemistry-2015, etc. In addition, he was invited to participate in NOST-2014 (National Organic Symposium Trust).Bhuwan B. Mishra
was born in Uttar Pradesh, India, in 1977. He started his doctoral research at the Department of Chemistry, Centre of Advanced Study, Banaras Hindu University, Varanasi, India, in 2005, and obtained his Ph.D. degree in 2009 under the supervision of Prof. Vyasji Tripathi. He then worked as a Council of Scientific & Industrial Research (CSIR) Research Associate with Dr. V. K. Tiwari. He recently joined the Center of Innovative and Applied Bioprocessing (CIAB), Mohali, India, as a Scientist-C to start his independent research career. He has significantly contributed toward the isolation and characterization of natural products and the development of novel synthetic methodologies for numerous heterocyclics and carbohydrate derivatives of great medicinal value. He has published over 37 papers, including original articles and book chapters in national and international journals and books. He has received several prestigious awards, namely, the Young Scientist Award (2010–2011) from the Council of Science & Technology (CST), Uttar Pradesh, India, and the Fast Track Young Scientist Project (2013) from the Department of Science & Technology (DST), New Delhi, India.Kunj B. Mishra
was born in 1986 in Bhabhua, Bihar, India. He completed his B.Sc. (2006) and M.Sc. (organic chemistry, 2008) degrees from Dr. B. R. Ambedkar University, Agra, India. He passed the CSIR-UGC NET (Council of Scientific & Industrial Research-University Grants Commission National Eligibility Test) qualifying exam in 2011 and joined the Ph.D. program at the Department of Chemistry, Banaras Hindu University (Varanasi, India), under the guidance of Dr. V. K. Tiwari on a project entitled “Cu-Catalysed Click Reaction in Carbohydrate Chemistry”. He was awarded the Young Scientist Award (YSA) by the United Group of Institutions, Allahabod, India (in 2014), and Best Poster Award-2014 at the 6th NIPER (RBL)-CDRI (National Institute of Pharmaceutical Education and Research (Raebareli)-Central Drug Research Institute) symposium. He has contributed about 10 publications in national and international journals and recently submitted his Ph.D. thesis.Nidhi Mishra
was born in Allahabad, Uttar Pradesh, India, in 1984. She obtained her B.Sc. (2005) and M.Sc. (organic chemistry as specialization, 2007) degrees in chemistry from the University of Allahabad, Allahabad, India. She worked as a synthetic chemist on a drug discovery project related to the development of heterocyclic skeletons of pharmaceutical interest at Chembiotek Research International (a contract research organization, Kolkata, India) from 2007 to 2010. After obtaining a Junior Research Fellowship from the CSIR-UGC NET (Council of Scientific & Industrial Research-University Grants Commission National Eligibility Test) in 2014, she joined the Department of Chemistry at Banaras Hindu University for her Ph.D. degree under the guidance of Dr. V. K. Tiwari. Her topic of interest is sugar-based organocatalysis, and presently, she is working on the development of carbohydrate-based organocatalysts using click chemistry and their application in stereoselective synthesis.Anoop S. Singh
was born in Varanasi, Uttar Pradesh, India, in 1986. He obtained his B.Sc. (2008) and M.Sc. degrees in chemistry (specializing in organic chemistry, 2010) from the Udai Pratap Autonomus Institution, Varanasi, India. After completing the qualifying exams, including the Common Entrance Test (CET) (2012), Graduate Aptitude Test in Engineering (GATE) (2013), and National Eligibility Test-Lectureship (NET-LS) (in 2013), he joined the Department of Chemistry at Banaras Hindu University (Varanasi, India) for his Ph.D. degree under the guidance of Dr. V. K. Tiwari. His doctoral research is focused on the development of a novel synthetic methodology through benzotriazole ring cleavage.Xi Chen
is a Professor in the Department of Chemistry at the University of California—Davis, United States. She received her B.S. degree in chemistry from Xiamen University, China, in 1994 and her Ph.D. degree in biological/organic chemistry from Wayne State University, United States, in 2000. She worked at Neose Biotechnologies, Inc. for 21/2 years before joining the faculty of the Department of Chemistry at the University of California—Davis in August 2003. Her group strives to understand carbohydrate-related biological processes in the areas of cancer, inflammation, immunology, and viral and bacterial infection. The current research focuses are (1) developing chemoenzymatic approaches for synthesizing structurally defined complex oligosaccharides and glycoconjugates, (2) studying carbohydrate–protein/cell interactions and exploring the functions of carbohydrates as potential prebiotics and antimicrobials, (3) collaborative crystal structure and mutagenesis studies of glycosyltransferases and other carbohydrate biosynthetic enzymes, and (4) designing and synthesizing sialidase inhibitors. Prof. Chen has contributed more than 140 peer-reviewed publications and over 20 patents. Prof. Chen is an Associate Editor of Carbohydrate Research and serves on the editorial board of Trends in Carbohydrate Research. - ISSN：1520-6890
文摘
Cu(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the “click reaction”, serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.