Chemical Sciences Seminars

Application of Iminoboronate in Chemistry and Biology

by Dr. Anupam Bandyopadhyay (Dept. of Chemistry, Massachusetts Institute of Technology, USA)

Thursday, September 14, 2017 from to (Asia/Kolkata)
at AG-80
In past decades, dynamic covalent chemistry has shown its great potential in the area of combinatorial chemistry and molecular recognition. Nonetheless, in this area, a few reactions have been explored that can allow selective recognition of endogenous nucleophile in reversible manner at physiological pH. Iminoboronate chemistry is one of them, which allow to capture amine at neutral pH. Here, I will present, how the fundamental understanding of iminoboronate complex formation was leveraged for numerous biological applications. Iminoboronate chemistry was known, however, it was poorly understood. For the first time, my work has revealed the dynamic nature of iminoboronate formation at physiological conditions.
In this talk, I will focus first on the dynamic covalent recognition of biologically important molecules via iminoboronate chemistry. Using this unique chemistry, I developed strategies for the specific recognition of gram-positive bacteria in blood serum [1]. Importantly, this approach has the potential to transform the way bacterial infection diagnostics are performed in clinical setting. Harnessing the power of this iminoboronate formation, I also developed a new and efficient synthetic access for modular cyclic peptides [2] along with an unprecedented bioorthogonal reaction [3]. For instance, the impact of these findings were illustrated by a new bioorthogonal labeling technology to detect gramnegative bacteria selectively. To take the kinetic advantage of iminoboronate formation, a strategy of fast and selective conjugation of N-terminal cysteine containing protein will be demonstrated [4].
1.      Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids. Bandyopadhyay, A., MaCarthy, K., Kelly, M., Gao, J. Nat. Commun., 2015, 6:6561.
2.      Iminoboronate-based peptide cyclization that responds to pH, oxidation, and small molecule modulators. Bandyopadhyay, A., Gao, J.; J. Am. Chem. Soc., 2016, 138, 2098.
3.      Fast Diazaborine Formation of Semicarbazide Enables Facile Labeling of Bacterial Pathogens. Bandyopadhyay, A., Cambray, S., Gao, J.; J. Am. Chem. Soc., 2017, 139, 871.
Fast and selective labeling of N-terminal cysteines at neutral pH via thiazolidino boronate formation. Bandyopadhyay, A., Cambray, S., Gao, J. Chem. Sci., 2016, 7, 4589.