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    Home > Research team of Professor Zhang Wanbin of Shanghai Jiaotong University: IR / Cu Bimetallic synergetic catalytic system for the stereodivergent synthesis of unnatural α, α - disubstituted α - amino acids

    Research team of Professor Zhang Wanbin of Shanghai Jiaotong University: IR / Cu Bimetallic synergetic catalytic system for the stereodivergent synthesis of unnatural α, α - disubstituted α - amino acids

    • Last Update: 2018-03-13
    • Source: Internet
    • Author: User
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    Introduction: unnatural α, α - disubstituted α - amino acids play a very important role in biochemistry and pharmaceutical research, especially α, α - disubstituted α - amino acids with adjacent chiral centers widely exist in natural products and drug molecular structures with biological activities Recently, Professor Zhang Wanbin's research team of Shanghai Jiaotong University has made new breakthroughs in this field ( DOI:
    10.1021/jacs.8b00187 )。
    Profile of Professor Zhang Wanbin, special professor of Shanghai Jiaotong University In 1985, he graduated from the Chemistry Department of East China University of science and technology, and in 1988, he held a master's degree in Chemistry Department of East China University of science and technology From 1993 to 1997, he won a Japanese government scholarship to study for a Ph.D in the Department of Applied Chemistry, Department of engineering, Osaka University, Japan From 1997 to 2001, he was an assistant professor in the Department of Applied Chemistry, Department of engineering, Osaka University, Japan From 2001 to 2003, he was the director researcher of Yokohama comprehensive research institute, Mitsubishi Chemical Co., Ltd., Japan Since 2003, he has been a professor in the school of chemistry and chemistry, Shanghai Jiaotong University Since 2009, he has also been a professor of Shanghai Jiaotong University Professor of School of medicine, was hired as a special professor of Shanghai Jiaotong University in 2013 Since October 2017, director of Shanghai Key Laboratory of chiral drug molecular engineering, Shanghai Jiaotong University Professor Zhang Wanbin presided over and participated in a number of research topics, such as the national major science and technology project of "major new drug creation", the key and general programs of the National Natural Science Foundation, the excellent young teachers funding program of the Ministry of education, the major and key science and technology research projects of the Shanghai Municipal Science and Technology Commission and the economic and Information Technology Commission, the international cooperation projects, and the research and production cooperation projects with many enterprises He has published more than 180 papers in SCI journals including j.am Chem SOC And angelw Chem Int ed., and has been invited to participate in the preparation of three English Monographs (three chapters) on asymmetric catalysis and drug synthesis by Wiley VCH and other publishers Professor Zhang Wanbin has achieved a number of scientific research results for industrial application, among which "artemisinin high efficiency artificial synthesis" was selected into the top ten domestic science and technology news in 2012 and the top ten science and technology achievements in Shanghai in 2012 In addition, Professor Zhang Wanbin was awarded the title of teacher's moral model of Shanghai Jiaotong University in 2008-2009, the most popular tutor of Shanghai Jiaotong University in 2011, the top ten Kaiyuan teachers' award of Shanghai Jiaotong University in 2012, the Shanghai Education Talent Award in 2012, the Thieme Chemistry Journal Award in 2013, and the outstanding discipline leader of Shanghai in 2014 In 2013 and 2015, he was awarded Excellent Doctoral Dissertation instructor in Shanghai In 2015, he won 100 most influential international academic papers in China In 2016, it was selected as the leading talent in Shanghai In 2016, he was granted special government allowance by the State Council Frontier research achievements: IR / Cu Bimetallic co catalysis system is used for the synthesis of α, α - disubstituted α - amino acids in three-dimensional divergent way The biological activity of α - disubstituted α - amino acids largely depends on their absolute and relative three-dimensional configuration Therefore, the development of a convenient and predictable methodology for the synthesis of all stereoisomers of the target product can not only obtain amino acids with different biological activities, but also facilitate the study of their structure activity relationship, so as to accelerate the discovery and development of drugs So far, most of the methods have been to change additives or different catalysts to solve this problem How to use the same materials to construct all stereoisomers under the same reaction conditions has always been a challenge The research group of Zhang Wanbin, Professor of Shanghai Jiaotong University, has been devoted to the development of cooperative catalytic system for a long time and applied this strategy to asymmetric allyl substitution reaction In recent years, the team has successfully developed a synergistic catalytic reaction system of palladium, small molecule catalyst and alcohol solvent with hydrogen bond (chem SOC Rev., 2015, 44, 7929-7967; chem Rec., 2016, 16, 2687-2696) The catalytic system can successfully use allylamine, allyl alcohol and allylic ether containing inert leaving group in allylic reaction of simple ketones (J am Chem SOC., 2011, 133, 19354-19357; angel Chem Int ed., 2014, 53, 6776-6780; org Lett., 2014, 16, 1570-1573; chem Commun 2017, 53, 5151-5154) Compared with the rapid development of organic and metal catalytic systems, although the chiral bimetallic catalytic system has a wider range of applications and more efficient synergistic effect, there are very few researches in this area Recently, the team has carried out a series of research work around bimetal collaborative catalysis system (invitedreview: org BIOMOL Chem., 2017, 15, 9747-9759) In 2016, the research team reported the first new stereodivergent chemical reaction based on the two handed metal catalysis strategy, that is, a bimetallic synergetic catalytic system composed of iridium catalyst modified by chiral phosphide ligands and zinc catalyst modified by chiral amino alcohols was developed for stereodivergent allylation of Hydroxyketones (j.am.chem.soc., 2016, 138, 11093-11096; Org Lett , 2017 , 19 , 5513-5516)。 Subsequently, the team developed a Pd / Cu Bimetallic coordinated catalytic reaction and directly used it for the asymmetric allylation of amino acids and oligopeptides (j.am Chem SOC., 2017, 139, 9819-9822; chem Commun., 2018, 54, 599-602) In view of the unique advantages of bimetallic catalytic system in reaction development and stereoscopic control, the team has recently successfully developed a new IR / Cu Bimetallic collaborative catalytic system and applied it to stereoscopic divergent synthesis of non natural α - amino acids A series of allyl substrates and aldimine esters can be successfully used in the catalytic system, with the highest yield of 96%, the stereoselectivity of > 99% and the enantioselectivity of > 20:1 In addition, the catalytic products can be used for the stereodivergent synthesis of aspartic acid analogues through simple transformation As a subtype selective blocker of glutamate transporters, these compounds can regulate the central nervous system of mammals This achievement was recently published in the Journal of the American Chemical Society (j.am Chem SOC., 2018, 140, 2080-2084) The first author of this article is Huo Xiaohong, a postdoctoral student of Shanghai Jiaotong University Today, Professor Zhang Wanbin's research team pays more and more attention to people and scientific research in the economic life of science and technology elements, China ushered in the "node of science and technology explosion" Behind the progress of science and technology is the work of countless scientists In the field of chemistry, in the context of the pursuit of innovation driven, international cooperation has been strengthened, the influence of Returned Scholars in the field of R & D has become increasingly prominent, and many excellent research groups have emerged in China For this reason, CBG information adopts the 1 + X reporting mechanism CBG information, chembeango app, chembeango official microblog, CBG wechat subscription number and other platforms jointly launch the column of "people and scientific research", approach the domestic representative research group, pay attention to their research, listen to their stories, record their demeanor, and explore their scientific research spirit.
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