Fasan, Rudi - University of Rochester - Department of Chemistry

个人简介

Rudi Fasan was born in Italy and studied Pharmaceutical Chemistry at the University of Padua, where he received his undergraduate degree (B.S.) with the highest honors in 1999. After serving mandatory military service in Italy and Romania (2000-2001), he joined the group of Prof. John Robinson at the University of Zurich (Switzerland) as a graduate student, working on the design and synthesis of beta-hairpin protein epitope mimetics. In 2005, he joined Prof. Frances Arnold's group at the California Institute of Technology as a Swiss National Science Foundation postdoctoral fellow, working on the directed evolution of P450 enzymes for alkane oxidation. Rudi began his independent career as a member of the Department of Chemistry at the University of Rochester in 2008 and was promoted to the rank of Full Professor in 2018. In 2019, he became the inaugural recipient of the Andrew S. Kende endowed Chair in Synthetic Organic Chemistry. He is the Director of the NIH-funded T32 program in Chemistry-Biology Interface (CBI) and of the NSF-funded Chemistry Research for Medicine and Energy Research Experience for Undergraduates (REU) Program at the University of Rochester. His awards include a Swiss National Science Foundation Postdoctoral Fellowship (2005-2007), the 2007 Friedrich-Weygand Outstanding Graduate Research Award, Provost Multidisciplinary Research Award (2011), University Research Award (2016), the 2014 Tetrahedron Young Investigator Award in Bioorganic and Medicinal Chemistry, 2020 Goergen Award for Excellence in Undergraduate Teaching, and the 2020 International Award for Creative Work from the Japan Society of Coordination Chemistry. Andrew S. Kende Endowed Chair of Synthetic Organic Chemistry (2019-current), University of Rochester, Rochester, NY Professor of Chemistry (2018-current), University of Rochester, Rochester, NY Professor of Oncology (2018-current), Wilmot Cancer Center, University of Rochester Medical Center, Rochester, NY Associate Professor of Chemistry (2014-2018), University of Rochester, Rochester, NY Assistant Professor of Chemistry (2008-2014), University of Rochester, Rochester, NY SNSF Postdoctoral Fellow (2005-2008), California Institute of Technology, Pasadena, CA Ph.D. in Bioorganic Chemistry (2001-2005), University of Zurich, Switzerland B.S. in Pharmaceutical Chemistry (1999), University of Padua, Italy

研究领域

Our group is interested in the design, development, and investigation of novel chemo-biosynthetic and chemo-enzymatic strategies for streamlining the discovery and synthesis of biologically active molecules. Our research program encompasses three major areas, whose ultimate goals include (a) implementing general platforms for the discovery of potent and selective inhibitors of protein-protein interactions; (b) developing late-stage C−H functionalization strategies for streamlining the synthesis and elaboration of complex molecules, and in particular bioactive natural products; and (c) developing efficient and sustainable biocatalytic methods for the asymmetric construction of C−C and C-heteroatom bonds. All our projects involve the synergistic integration of chemical synthesis, protein chemistry, molecular biology, rational design and molecular evolution methods toward the development of molecular discovery platforms and biocatalytic systems of practical and broad utility. Macrocyclic Peptide Inhibitors of Protein-Protein Interactions Late-Stage C—H Functionalization and Diversification of Complex Molecules Engineered and Artificial Metalloprotein Catalysts for Biological Reactions

近期论文

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Enantioselective single and dual a-C–H bond Functionalization of Cyclic Amines via Enzymatic Carbene Transfer. Ren X, Couture BM, Liu N, Lall MS, Kohrt JT, and Fasan* R. J. Am. Chem. Soc. 2022; accepted. Dehaloperoxidase Catalyzed Stereoselective Synthesis of Cyclopropanol Esters. Siriboe MG, Vargas DA, and Fasan* R. Journal of Organic Chemistry 2022; accepted. Engineered Myoglobin Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions. Siriboe MG, and Fasan* R. Bull. Chem. Soc. Jpn. 2022; 80 4-13. Highly stereoselective and enantiodivergent synthesis of cyclopropylphosphonates with engineered carbene transferases. Ren X, Chandgude AL, Carminati DM, Shen Z, Khare SD and Fasan* R. Chemical Science 2022; 61, 11, 1041–1054. Tuning Enzyme Thermostability via Computationally Guided Covalent Stapling and Structural Basis of Enhanced Stabilization. Iannuzzelli JA, Bacik JP, Moore EJ, Shen Z, Irving EM, Vargas DA, Khare* SD, Ando* N, and Fasan* R. Biochemistry 2022; 61, 11, 1041–1054. Enantioselective Synthesis of alpha-Trifluoromethyl Amines via Biocatalytic N–H Bond Insertion with Acceptor-Acceptor Carbene Donors. Nam D, Tinoco A, Shen Z, Adukure RD, Sreenilayam D, Khare* SD, and Fasan* R. J. Am. Chem. Soc. 2022; 144 (6) 2590–2602. Nanoparticle-Mediated Delivery of Micheliolide Analogs to Eliminate Leukemic Stem Cells in the Bone Marrow. Ackun-Farmmer MA, Hanan Alwaseem H, Counts M, Bortz A, Giovani S, Frisch* BJ, Fasan* R, and Benoit DSW. Advanced Therapeutics 2022; 5 (1) 2100100. Engineered and artificial metalloenzymes for selective C–H functionalization. Ren X, and Fasan* R. Current Opinion in Green and Sustainable Chemistry 2021; 31. Cyclic peptides with a distinct arginine-fork motif recognize the HIV trans-activation response RNA in vitro and in cells. Chavali† SS, Mali† SM, Jenkins JL, Bonn RMS, Saseendran Anitha A, Bennett, RP, Smith, HC, Fasan* R, and Wedekind* JE. J. Biol. Chem. 2021; 297, 6. Comprehensive Structure–Activity Profiling of Micheliolide and its Targeted Proteome in Leukemia Cells via Probe-Guided Late-Stage C–H Functionalization. Alwaseem H, Giovani S, Crotti M, Welle K, Jordan G T, Ghaemmaghami S, and Fasan* R. ACS Cent. Sci. 2021; 7 (5) 841–857. A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones. Nam D, Steck V, Potenzino RJ, and Fasan* R. J. Am. Chem. Soc. 2021; 143(5) 2221–2231. Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2‐Containing Trisubstituted Cyclopropanes. Carminati DM, Decaens J, Couve‐Bonnaire S, Jubault P, and Fasan* R. Angew. Chem. Int. Ed. 2021; 60 1-6. Co-crystal structures of HIV TAR RNA bound to lab-evolved proteins show key roles for arginine relevant to the design of cyclic peptide TAR inhibitors. Chavali SS, Mali SM, Jenkins JL, Fasan R,and Wedekind* JE. J. Biol. Chem. 2020; 295(49) 16470-16486. An enzymatic platform for the highly enantioselective and stereodivergent construction of cyclopropyl-delta-lactones. Ren†X, Liu†N, Chandgude AL, and Fasan* R. Angew. Chem. Int. Ed. 2020; 59 2-8. Enantioselective Synthesis of Chiral Amines via Biocatalytic Carbene N-H Insertion. Steck V, Carminati DM, Johnson NR, and Fasan* R. ACS Catal. 2020; 10 10967−10977. Strategies for the Expression and Characterization of Artificial Myoglobin-based Carbene Transferases. Carminati DM, Moore EJ, and Fasan* R. Methods in Enzymology 2020; 644 35-61. Organic Solvent Stability and Long-term Storage of Myoglobin-based Carbene Transfer Biocatalysts. Pineda-Knauseder† AJ, Vargas† DA, and Fasan* R. Biotechnology and Applied Biochemistry 2020; 67 (4) 516- 526. Expanded toolbox for directing the biosynthesis of macrocyclic peptides in bacterial cells. Iannuzzelli JA, and Fasan* R. Chemical Science 2020; 11, 6202-6208. Synergistic catalysis in an artificial enzyme. Ren X, and Fasan* R. Nature Chemistry 2020; 3, 184-185. C-H Amination via Nitrene Transfer Catalyzed by Mononuclear Non‐Heme Iron‐Dependent Enzymes. Vila† MA, Steck† V, Giordano SR, Carrera* I, and Fasan* R. ChemBioChem 2020; 21 (14), 1981- 1987. Mechanism-Guided Design and Discovery of Efficient Cytochrome P450 Derived C-H Amination Biocatalysts. Steck† V, Kolev† JN, Ren X, and Fasan* R. J. Am. Chem. Soc. 2020; 142 (23), 10343–10357. Blocking SHH/Patched interaction triggers tumor growth inhibition through Patched-induced apoptosis. Bissey AP, Mathot P, Guix C, Jasmin M, Goddard I, Costechareyre C, Gadot N, Delcros JG, Mali SM, Fasan R, Arrigo AP, Dante R, Ichim G, Mehlen P, Fombonne J. Cancer Research 2020; 80 (10) 1970-1980. MOrPH-PhD: an integrated phage display platform for the discovery of functional genetically-encoded peptide macrocycles. Owens AE, Iannuzzelli JA, Gu Y, and Fasan* R. ACS Cent. Sci. 2020; 6 (3), 368–381. Highly Stereoselective Synthesis of Fused Cyclopropane-γ-Lactams via Biocatalytic Iron-Catalyzed Intramolecular Cyclopropanation. Ren† X, Chandgude† AL, and Fasan* R. ACS Catal. 2020; 10(3) 2308-2313. Structure of sonic hedgehog protein in complex with Zn(II) and Mg(II) reveals ion coordination plasticity relevant to peptide drug design. Bonn-Breach R, Gu Y, Jenkins J, Fasan R, Wedekind W*. Acta Crystallographica D 2019; D75 969-979. A continuing career in biocatalysis: Frances H. Arnold. Fasan* R, Kan* SBJ, Zhao* H. ACS Catal. 2019; 9 9683-9697 (Invited article in honour of 2018 Nobel Laureate Frances Arnold) Stereoselective Cyclopropanation of Electron-Deficient Olefins with a Cofactor Redesigned Carbene Transferase Featuring Radical Reactivity. Carminati D, and Fasan* R. ACS Catal. 2019; 9 9683-9697. Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N–H Insertion. Steck V, Sreenilayam G, and Fasan* R. Synlett 2019; 30 A-F. Mechanistic Investigation of Biocatalytic Heme Carbenoid Si−H Insertions. Khade R, Chandgude A, Fasan* R and Zhang* Y. ChemCatChem 2019; 11,13 3101-3108. Biocatalytic Strategy for Highly Diastereo‐ and Enantioselective Synthesis of 2,3‐Dihydrobenzofuran‐Based Tricyclic Scaffolds. Vargas D, Khade R, Zhang* Y and Fasan* R. Angew. Chem. Int. Ed. 2019; 58,30 10148-10152. Stereodivergent Intramolecular Cyclopropanation Enabled by Engineered Carbene Transferases. Chandgude AL, Ren X, and Fasan* R. J. Am. Chem. Soc. 2019; 141, 23 9145-9150. Effect of proximal ligand substitutions on the carbene and nitrene transferase activity of myoglobin. Moore E , and Fasan* R. Tetrahedron 2019; 75, 16 2357-2363. Origin of High Stereocontrol in Olefin Cyclopropanation Catalyzed by an Engineered Carbene Transferase. Tinoco A, Wei Y, Bacik JP, Carminati D, Moore E , Ando N, Zhang Y , and Fasan* R. ACS Catal. 2019; 9 1514-1524.