Yudin, Andrei - University of Toronto - Department of Chemistry

个人简介

Professor Andrei K. Yudin is a Tier I Canada Research Chair in Medicine by Design at the University of Toronto. He obtained his B.Sc. degree at the Moscow State University in 1992 and his Ph.D. degree at the University of Southern California under the direction of Professors G. K. Surya Prakash and George A. Olah in 1996. He subsequently took up a postdoctoral position in the laboratory of Professor K. Barry Sharpless at the Scripps Research Institute. In 1998, he started his independent career at the University of Toronto. He received early tenure, becoming an Associate Professor in 2002, and received an early promotion to the rank of a Full Professor in 2007. He currently serves as an Associate Editor for Chemical Science, handling submissions in the area of organic chemistry.

研究领域

Macrocycles and peptides We develop and apply new methods for making complex macrocycles. This effort involves discovery of new cyclization reactions and careful spectroscopic characterization of our molecules with the goal of understanding their conformation. Reaction discovery Our hypothesis is that new chemical transformations can arise from combinations of half-reactions, which can be either endothermic or exothermic. Several ongoing projects tackle this area and seek to discover new transformations by combining the elements of existing processes in entirely new ways. Amphoteric molecules Bifunctional structures that combine seemingly incompatible reactivity centers (e.g. a nucleophile and an electrophile) are a long-standing research area in our group. Over the years we have developed synthetic reagents that are broadly used in chemical synthesis. Chemical biology The main objective of this effort is to apply complex macrocycles and boron-containing molecules to interrogate biological targets. We collaborate with many labs all over the world who use our molecules in order to perform biochemical assays and cell-based work.

近期论文

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Li, Y.; Fan, W. - X.; Luo, S.; Trofimova, A.; Liu, Y.; Xue, J. - H.; Yang, L.; Li, Q.; Wang, H.; Yudin, A. K. Β-Boron Effect Enables Regioselective And Stereospecific Electrophilic Addition To Alkenesboron Effect Enables Regioselective And Stereospecific Electrophilic Addition To Alkenes. Journal of the American Chemical Society 2023. Tien, C. - H.; Lough, A. J.; Yudin, A. K. Iminologous Epoxide Ring-Closure. Chemical Science 2022, 13 (41), 12175 - 12179. Diaz, D. B.; Saunders, G.; Sprang, F.; Yudin, A. K.; McTiernan, T. Navigating Complex Peptide Structures Using Macrocycle Conformational Maps. RSC Chemical Biology 2022. Saunders, G. J.; Yudin, A. K. Property‐Driven Development Of Passively Permeable Macrocyclic Scaffolds Using Heterocycles**. Angewandte Chemie International Edition 2022. Huh, S.; Saunders, G. J.; Yudin, A. K. Single Atom Ring Contraction Of Peptide Macrocycles Using Cornforth Rearrangement. Angewandte Chemie International Edition 2022. Yudin, A. Synthetic Tools That Enable Synthesis And Understanding Of Bioactive Macrocycles. Synlett 2022. Trudel, V.; Brien, C.; Tan, J.; Yudin, A. K. Towards Depeptidized Aminoboronic Acid Derivatives Through The Use Of Borylated Iminium Ions. Chemical Communications 2022. Holownia, A. E.; Apte, C. N.; Yudin, A. K. Acyl Metalloids: Conformity And Deviation From Carbonyl Reactivity. Chemical Science 2021. Trofimova, A.; Holownia, A.; Tien, C. - H.; Širvinskas, M. J.; Yudin, A. K. Acylboronates In Polarity-Reversed Generation Of Acyl Palladium(Ii) Intermediatesacylboronates In Polarity-Reversed Generation Of Acyl Palladium(Ii) Intermediates. Organic Letters 2021, 23 (9), 3294 - 3299. Diaz, D. B.; Appavoo, S. D.; Bogdanchikova, A. F.; Lebedev, Y.; McTiernan, T. J.; Gomes, Gdos Passos; Yudin, A. K. Illuminating The Dark Conformational Space Of Macrocycles Using Dominant Rotors. Nature Chemistry 2021. Trudel, V.; Tien, C. - H.; Trofimova, A.; Yudin, A. K. Interrupted Reactions In Chemical Synthesis. Nature Reviews Chemistry 2021. Kaldas, S. J.; Tien, C. - H.; Gomes, Gdos Passos; Meyer, S.; Sirvinskas, M.; Foy, H.; Dudding, T.; Yudin, A. K. Oxidative Rearrangement Of Mida ( N-Methyliminodiacetic Acid) Boronates: Mechanistic Insights And Synthetic Applications . Organic Letters 2021. Soor, H. S.; Diaz, D. B.; Tsui, K. Yi; Calvopiña, K.; Bielinski, M.; Tantillo, D. J.; Schofield, C. J.; Yudin, A. K. Synthesis And Application Of Constrained Amidoboronic Acids Using Amphoteric Boron-Containing Building Blockssynthesis And Application Of Constrained Amidoboronic Acids Using Amphoteric Boron-Containing Building Blocks. The Journal of Organic Chemistry 2021. Tien, C. - H.; Trofimova, A.; Shao, W.; Yudin, A. K. Synthesis Of Borylated Hydrazino Acid Derivatives. Synthesis 2021. Soor, H. S.; Diaz, D. B.; Burton, K. I.; Yudin, A. K. Synthesis Of Fluorinated Aminoalkylboronic Acids From Amphoteric Α‐Boryl Aldehydes. Angewandte Chemie International Edition 2021, 60 (30), 16366 - 16371. Kobori, S.; Huh, S.; Appavoo, S. D.; Yudin, A. K. Two-Dimensional Barriers For Probing Conformational Shifts In Macrocycles. Journal of the American Chemical Society 2021. Ming, W.; Soor, H. S.; Liu, X.; Trofimova, A.; Yudin, A. K.; Marder, T. B. Α-Aminoboronates: Recent Advances In Their Preparation And Synthetic Applications. Chemical Society Reviews 2021, 50 (21), 12151 - 12188. Huh, S.; Appavoo, S. D.; Yudin, A. K. Amidine Functionality As A Conformational Probe Of Cyclic Peptides. Organic Letters 2020. Lebedev, Y. N.; Apte, C.; Cheng, S.; Lavigne, C.; Lough, A.; Seferos, D. S.; Aspuru-Guzik, A.; Yudin, A. K. Boramidine: A Versatile Structural Motif For The Design Of Fluorescent Heterocycles. J Am Chem Soc 2020. Tien, C. - H.; Trofimova, A.; Holownia, A.; Kwak, B. S.; Larson, R. T.; Yudin, A. K. Carboxyboronate As A Versatile In Situ Co Surrogate In Palladium‐Catalyzed Carbonylative Transformations. Angewandte Chemie International Edition 2020. Apte, C. Nitin; Diaz, D. B.; Adrianov, T.; Yudin, A. K. Grafting Bis(Heteroaryl) Motifs Into Ring Structures. European Journal of Organic Chemistry 2020. Revie, N. M.; Robbins, N.; Whitesell, L.; Frost, J. R.; Appavoo, S. D.; Yudin, A. K.; Cowen, L. E. Oxadiazole-Containing Macrocyclic Peptides Potentiate Azole Activity Against Pathogenic Species. mSphere 2020, 5 (2). C. Lee, F.; Tien, C. - H.; Adachi, S.; Yudin, A. K. Synthesis Of Α-Bromoacetyl Mida Boronate. Organic Syntheses 2020, 97, 157 - 171. Yudin, A. K. Synthetic Half-Reactions. Chemical Science 2020. Holownia, A.; Tien, C. - H.; Diaz, D. B.; Larson, R. T.; Yudin, A. K. Carboxyboronate: A Versatile C1-Building Block. Angewandte Chemie International Edition 2019. Appavoo, S. D.; Huh, S.; Diaz, D. B.; Yudin, A. K. Conformational Control Of Macrocycles By Remote Structural Modification. Chem Rev 2019. Yamaguchi, A.; Kaldas, S. J.; Appavoo, S. D.; Diaz, D. B.; Yudin, A. K. Conformationally Stable Peptide Macrocycles Assembled Using The Petasis Borono-Mannich Reaction. Chem Commun (Camb) 2019. Tan, J.; Grouleff, J. J.; Jitkova, Y.; Diaz, D. B.; Griffith, E. C.; Shao, W.; Bogdanchikova, A. F.; Poda, G.; Schimmer, A. D.; Lee, R. E.; Yudin, A. K. De Novo Design Of Boron-Based Peptidomimetics As Potent Inhibitors Of Human Clpp In The Presence Of Human Clpx. J Med Chem 2019, 62 (13), 6377-6390. Smolyar, I. V.; Yudin, A. K.; Nenajdenko, V. G. Heteroaryl Rings In Peptide Macrocycles. Chem Rev 2019. Mader, P.; Mendoza-Sanchez, R.; Iqbal, A.; Dong, A.; Dobrovetsky, E.; Corless, V. B.; Liew, S. K.; Houliston, S. R.; De Freitas, R. Ferreira; Smil, D.; Sena, C. C. Dela; Kennedy, S.; Diaz, D. B.; Wu, H.; Dombrovski, L.; Allali-Hassani, A.; Min, J.; Schapira, M.; Vedadi, M.; Brown, P. J.; Santhakumar, V.; Yudin, A. K.; Arrowsmith, C. H. Identification And Characterization Of The First Fragment Hits For Setdb1 Tudor Domain. Bioorg Med Chem 2019, 27 (17), 3866-3878. Trudel, V.; Yudin, A. K. Nucleophilic Boron Clusters Lead To New Borylation Methods. Chem 2019. Kaldas, S.; Kran, E.; Mück-Lichtenfeld, C.; Yudin, A.; Studer, A. Reaction Of Vinylaziridines With Arynes: Synthesis Of Benzazepines And Branched Allyl Fluorides. Chemistry – A European Journal 2019. Soor, H. S.; Hansen, J.; Diaz, D. B.; Appavoo, S.; Yudin, A. K. Solid-Phase Synthesis Of Peptide Β-Aminoboronic Acids. Peptide Science 2019, 111 (1), e24072. Kaldas, S. J.; Yudin, A. K. Achieving Skeletal Diversity In Peptide Macrocycles Through The Use Of Heterocyclic Grafts. Chemistry - A European Journal 2018, 24 (28), 7074 - 7082. C. Lee, F.; Diaz, D. B.; Holownia, A.; Kaldas, S. J.; Liew, S. K.; Garrett, G. E.; Dudding, T.; Yudin, A. K. Amine Hemilability Enables Boron To Mechanistically Resemble Either Hydride Or Proton. Nature Chemistry 2018, 10 (10), 1062 - 1070. Tan, J.; Yudin, A. K. Borylated Reagents For Multicomponent Reactions. Drug Discov Today Technol 2018, 29, 51-60. Appavoo, S. D.; Kaji, T.; Frost, J. R.; Scully, C. C. G.; Yudin, A. K. Development Of Endocyclic Control Elements For Peptide Macrocycles. Journal of the American Chemical Society 2018, 140 (28), 8763 - 8770. Soor, H. S.; Appavoo, S. D.; Yudin, A. K. Heterocycles: Versatile Control Elements In Bioactive Macrocycles. Bioorganic & Medicinal Chemistry 2018, 26 (10), 2774 - 2779. Kaldas, S. J.; Rogova, T.; Nenajdenko, V. G.; Yudin, A. K. Modular Synthesis Of Β-Amino Boronate Peptidomimetics. The Journal of Organic Chemistry 2018, 83 (13), 7296 - 7302. Corless, V. B.; Holownia, A.; Foy, H.; Mendoza-Sanchez, R.; Adachi, S.; Dudding, T.; Yudin, A. K. Synthesis Of Α-Borylated Ketones By Regioselective Wacker Oxidation Of Alkenylboronates. Org Lett 2018, 20 (17), 5300-5303.