Kutateladze, Andrei - University of Denver - Department of Chemistry & Biochemistry

个人简介

John Evans Professor, University of Denver, 2009- University Distinguished Scholar, University of Denver, 2004 Dean, College of Natural Sciences and Mathematics, University of Denver, 2012- Professor, Department of Chemistry and Biochemistry, University of Denver, 2005- Associate Professor, Department of Chemistry and Biochemistry, University of Denver, 2001-2005 Assistant Professor, Department of Chemistry and Biochemistry, University of Denver, 1995-2001 Assistant Scientist, Department of Chemistry, University of Wisconsin - Madison, 1992-95 Research Associate, Department of Chemistry and Biochemistry, University of Denver, 1990-92 Assistant Professor, Department of Chemistry, Moscow State University, 1987-90.

研究领域

PHOTOASSISTED DOS Photochemical reactions initiated by light hold unparalleled promise for building complex molecular architectures and accessing challenging synthetic targets. In the past, with the exception of a few landmark syntheses, synthetic organic photochemistry was grossly underutilized by the synthetic community, although the recent explosion in photoredox catalysis gives hope that synthetic chemists are warming up to the idea that photochemistry could offer useful day-to-day tools for the synthetic chemistry toolbox. Still diversity-oriented synthesis (DOS) and combichem remain the areas where photochemical methods are blissfully absent. We are developing novel photoassisted synthetic methodologies, enabling us to gain rapid access to a number of new drug-like molecules, primarily complex nitrogen, oxygen, and sulfur-containing heterocycles. The ongoing revolution in metal-catalyzed sp2-sp2 coupling is blamed for biasing synthetic effort at the bench and "steering discovery efforts toward achiral, aromatic compounds" while natural products, possessing a broad spectrum of bioactivity, look nothing like the sp2-dominated aromatic heterocycles. Our photoassisted synthetic methodology aims to generate a variety of unique (poly)heterocyclic core scaffolds containing high number of sp3 carbons (see Lovering's Fsp3 saturation parameter) and possessing very few rotatable bonds.

近期论文

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Peculiar Reaction Products and Mechanisms Revisited with Machine Learning-Augmented Computational NMR. Novitskiy, I.M.; Kutateladze, A.G. J. Org. Chem., 2022, 87, (13), 8589-8598. [DOI: 10.1021/acs.joc.2c00749] Maximizing Step-Normalized Increases in Molecular Complexity: Formal [4+2+2+2] Photoinduced Cyclization Cascade to Access Polyheterocycles Possessing Privileged Substructures. Reddy, D.S.; Novitskiy, I.M.; Kutateladze, A.G. Angewandte Chem. Int. Ed., 2022, 61, (4), e202112573. [DOI: 10.1002/anie.202112573] DU8ML: Machine Learning-Augmented Density Functional Theory Nuclear Magnetic Resonance Computations for High-Throughput In Silico Solution Structure Validation and Revision of Complex Alkaloids. Novitskiy, I.M.; Kutateladze, A.G. J. Org. Chem., 2022, 87, (7), 4818-4828. [DOI: 10.1021/acs.joc.2c00169] Reassignment of Improbable Natural Products Identified through Chemical Principle Screening. Elyashberg, M.; Novitskiy, I. M.; Bates, R. W.; Kutateladze, A. G.; Williams, C. M. Eur. J. Org. Chem., 2022, 0. [DOI: 10.1002/ejoc.202200572] DU8+ Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety. Novitskiy, I.M.; Kutateladze, A.G. J. Org. Chem., 2021, 86, 17511-17515. [DOI: 10.1021/acs.joc.1c02291] Structure revision of ent-kaurane diterpenoids, isoserrins A, B, and D, enabled by DU8+ computation of their NMR spectral data. Novitskiy, I.M.; Holt, T.A.; Kutateladze, A.G. Mendeleev Comm. , 2021, 31, 300-301. [DOI: 10.1016/j.mencom.2021.05.007] The Discreet Structural Diversity of Briarellins: DU8+ Guided Multiple Structure Revisions Yielded Two Unknown Structural Types. Holt, T. A.; Reddy, D. S.; Huple, D. B.; West, L. M.; Rodriguez, A. D.; Crimmins, M. T.; Kutateladze, A. G. J. Org. Chem., 2020, 85, (9), 6201-6205. [DOI: 10.1021/acs.joc.0c00555] EBC-232 and 323:A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods. Maslovskaya, L. A.; Savchenk, A. I.; Krenske, E. H.; Chow, S.; Holt, T.; Gordon, V. A.; Reddell, P. W.; Pierce, C. J.; Parsons, P. G.; Boyle, G. M.; Kutateladze, A. G.; Williams, C. M. Chem. Eur. J., 2020, 26, 11862-11867. [DOI: 10.1002/chem.202001884] Stereochemical revision of xylogranatin F by GIAO and DU8+ NMR calculations. Liu, Y.; Holt, T. A.; Kutateladze, A. G.; Newhouse, T. R. Chirality, 2020, 32, 515-523. [DOI: 10.1002/chir.23189] Dichotomy in the reactivity of 2-methyltetrahydroquinazoline 1-oxides towards aldehydes: An unprecedented condensation with simultaneous reduction of the N-oxide fragment. Sedenkova, K. N.;Terekhin, A. V.; Abdrashitova, I. V.; Vasilenko, D. A.; Sadovnikov, K. S.; Gracheva, Y. A.; Grishin, Y. K.; Holt, T. A.; Kutateladze, A. G.; Kuznetsova, T. S.; Milaeva, E. R.; Averina, E. B. Tetrahedron Lett., 2020, 61, (11), 151605. [DOI: 10.1016/j.tetlet.2020.151605] Photoinitiated Cascade for Rapid Access to Pyrroloquinazolinone Core of Vasicinone, Luotonins, and Related Alkaloids. Reddy, D. S.; Kutateladze, A. G. Org. Lett., 2019, 21, (8), 2855-2858.. [DOI: 10.1021/acs.orglett.9b00858] Natural Products Containing the Oxetane and Related Moieties Present Additional Challenge for Structure Elucidation: a DU8+ Computational Case Study. Kutateladze, A. G.; Holt, T. A.; Reddy, D. S. J. Org. Chem., 2019, 84, (12), 7575-7586. [DOI: 10.1021/acs.joc.9b01005] Structure Validation of Complex Natural Products: Time to Change the Paradigm. What did Synthesis of Alstofolinine A Prove? Kutateladze, A. G.; Holt, T. A. J. Org. Chem., 2019, 84, (12), 8297-8299. [DOI: 10.1021/acs.joc.9b00969] Diastereoselective heterocyclization of geminal bromo-fluoro arylcyclopropanes by nitrosonium tetrafluoroborate: Access to 4-fluorinated isoxazolines and isoxazoles. Bondarenko, O. B.; Komarov, A. I.; Karetnikov, G. L.; Nikolaeva, S. N.; Zyk, N. V.; Holt, T. A.; Kutateladze, A. G. Tetrahedron, 2019, 75, (46), 130666. [DOI: 10.1016/j.tet.2019.130666] Reassignments and Corroborations of Oxo-Bridged Natural Products Directed by OSE and DU8+ NMR Computation. Kutateladze, A.G.; Krenske, E.H.; Williams, C.M. Angew. Chem. Int. Ed., 2019, 58, (21), 7107-7112. [DOI: 10.1002/anie.201902777] The value of universally available raw NMR data fortransparency, reproducibility, and integrity innatural product research. McAlpine, J.B.; Chen, S.-N.; Kutateladze, A.G.; et. al. Nat. Prod. Rep., 2019, 36, 35-107. [DOI: 10.1039/C7NP00064B] Access to 5-Fluoroisoxazoles via the Nitrosation of Geminal Bromo-Fluoro Arylcyclopropanes. Bondarenko, O.B.; Vinogradov, A.A.; Komarov, A.I.; Karetnikov, G.L.; Zyk, N.V.; Holt, T.; Kutateladze, A.G. Tetrahedron, 2019, 75, 2861-2865. [DOI: 10.1016/j.tet.2019.03.054] Novel π-Conjugated Systems Based on Pyrimidine N-Oxide. Sedenkova, K.N.; Kolodyazhnaya, J.V.; Vasilenko, D.A.; Gracheva Y.A.; Kharitonoshvili, E.V.; Grishin, Y.K.; Chistov, A.A.; Rybakov, V.B.; Holt, T.; Kutateladze, A.G.; Kuznetsova, T.S.; Milaeva, E.R.; Averina, E.B. Dyes and Pigments, 2019, 164, 72-81. [DOI: 10.1016/j.dyepig.2018.12.067] Structural insights into the π-π-π stacking mechanisms and DNA-binding activity of the YEATS domain. Klein, B.J.; Vann, K.R.; Andrews, F.H.; Wang, W.W.; Zhang, J.; Zhang, Y.; Beloglazkina, A.A.; Mi, W.; Li, Y.; Li, H.; Shi, X.; Kutateladze, A.G.; Strahl, B.D.; Liu, W.R.; Kutateladze, T.G. Nat. Commun., 2018, 9, 4574. [DOI: 10.1038/s41467-018-07072-6] Addressing the Challenges of Structure Elucidation in Natural Products Possessing the Oxirane Moiety. Kutateladze, A.G.; Kuznetsov, D.M.; Beloglazkina, A. A.; Holt, T. J. Org. Chem., 2018, 83, (15), 8341-8352. [DOI: 10.1021/acs.joc.8b01027]