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  English.dicp.cas.cn    Posted:2017-07-07
Lecture: Covalent Molecular Recognition via Iminoboronate Chemistry

Time: July 7, 2017, 9:30 am
Venue: Conference Room on the First Floor, Basic Energy Building
Lecturer: Professor GAO Jianmin, Associate Professor of Chemistry, Boston College


Professor GAO is a native of Shandong province, China. He received his college education at University of Science of Technology of China (USTC), where he received Guo MoRuo Fellowship, the highest honor a USTC undergraduate could have. In 1999, Professor GAO came to the United States to pursue graduate education, for which he worked with Professor Eric Kool in the Chemistry Department of Stanford University. As a graduate student, Professor GAO worked on nucleic acid chemistry, specifically on the synthesis and evaluation of novel DNA analogues. In 2004, Professor GAO moved to San Diego, where he carried out his post-doctoral research at The Scripps Research Institute. Working in the Kelly lab at Scripps, Professor GAO utilized chemical synthesis to interrogate the role of the polyamide backbone in protein folding and stability. He started his independent career in 2007 at Boston College, where he remains as a tenured Associate Professor. Professor GAO has established a unique program at the interface of organic chemistry and membrane biology, which seeks to develop synthetic, low-molecular-weight receptors for lipids of biological significance. Molecules as such can serve as powerful tools for research as well as therapeutics. In biology, small molecule recognition is typically accomplished by large proteins save a few exceptions from peptide natural products such as vancomycin. To create synthetic receptors like vancomycin, the GAO group has been researching on novel modes of target binding. Specifically, GAO and coworkers have ushered in the utilization of polar-p interaction (Acc. Chem. Res, 2013) and reversible covalent chemistry (Curr. Opin. Chem. Biol., 2017) in molecular design to target biomolecules. Complementary to these novel interactions, the GAO group has developed powerful conjugation reactions (JACS, 2016 &2017) to elicit peptide multicyclization, a strategy adapted by peptide natural products to favor target binding. These technological advances have allowed the GAO group to develop novel synthetic peptides to bind specific lipids. The innovative research has already seen over thirty independent publications and has attracted funding from NSF and NIH. Professor GAO has been recognized by a Smith Family Young Investigator Award from the Medical Foundation in Boston.


Molecular recognition underlies essentially every aspect of biology and selective inhibition of culprit molecules has been the guiding philsophy of medicinal chemistry. In nature, seletive association of molecules are primarily driven by noncovalent interactions, while covalent bond formation has been largely avoided due to the potential difficulty of dissociation. We and others have been developing reversible covalent chemistries, which can give rise to powerful strategies for targeting biomolecules. Specifcially, we have been investigating the iminoboronate chemistry with the goal of targeting biological amines. In contrast to imines (Schiff bases), which typically do not form in water, iminoboronates exhibit much improved thermodynamic stability, making it suitable for biological applications. In this seminar, I will present detailed characterziations of the dynamic iminiboronte formation under physiologic conditions. Biological applications of the iminoboronate chemistry have been explored in our laboratory in the context of antibiotics development. Specifically, we have reported the iminoboronate-enabled peptide bicyclization, as well as the covalent modification of Lys-PG, a bacterial lipid reponsible for resistance to cationic antibiotics. The details of these developements will be discussed as well.





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