Directed Evolution of Flavin-Dependent Halogenases for Site- and Atroposelective Halogenation of 3-Aryl-4(3 H )-Quinazolinones via Kinetic or Dynamic Kinetic Resolution

Snodgrass, Harrison M.; Mondal, Dibyendu; Lewis, Jared C.

doi:10.1021/jacs.2c07422

Directed Evolution of Flavin-Dependent Halogenases for Site- and Atroposelective Halogenation of 3-Aryl-4(3 H )-Quinazolinones via Kinetic or Dynamic Kinetic Resolution

Journal Article · 31 August 2022 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c07422· OSTI ID:1982067

Snodgrass, Harrison M. ^[1]; Mondal, Dibyendu ^[1]; ^[1]

Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States

Not provided.

Research Organization:: USDOE Joint Genome Institute (JGI), Walnut Creek, CA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC02-05CH11231

OSTI ID:: 1982067

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 36 Vol. 144; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (42)

Development of α-glucosidase inhibitors by room temperature C–C cross couplings of quinazolinones Garlapati, Ramesh; Pottabathini, Narender; Gurram, Venkateshwarlu Organic & Biomolecular Chemistry, Vol. 11, Issue 29 https://doi.org/10.1039/c3ob40636a	journal	January 2013
Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products Bringmann, Gerhard; Gulder, Tanja; Gulder, Tobias A. M. Chemical Reviews, Vol. 111, Issue 2 https://doi.org/10.1021/cr100155e	journal	February 2011
Discovery of a Covalent Inhibitor of KRAS ^G12C (AMG 510) for the Treatment of Solid Tumors Lanman, Brian A.; Allen, Jennifer R.; Allen, John G. Journal of Medicinal Chemistry, Vol. 63, Issue 1 https://doi.org/10.1021/acs.jmedchem.9b01180	journal	December 2019
Analysis of laboratory-evolved flavin-dependent halogenases affords a computational model for predicting halogenase site selectivity Andorfer, Mary C.; Evans, Declan; Yang, Song Chem Catalysis, Vol. 2, Issue 10 https://doi.org/10.1016/j.checat.2022.07.003	journal	October 2022
Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts Miyaji, Ryota; Asano, Keisuke; Matsubara, Seijiro Chemistry - A European Journal, Vol. 23, Issue 42 https://doi.org/10.1002/chem.201701707	journal	May 2017
Recent advances and new concepts for the synthesis of axially stereoenriched biaryls Wencel-Delord, J.; Panossian, A.; Leroux, F. R. Chemical Society Reviews, Vol. 44, Issue 11 https://doi.org/10.1039/c5cs00012b	journal	January 2015
Dynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Asymmetric Bromination Gustafson, J. L.; Lim, D.; Miller, S. J. Science, Vol. 328, Issue 5983 https://doi.org/10.1126/science.1188403	journal	June 2010
Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling Andorfer, Mary C.; Grob, Jonathan E.; Hajdin, Christine E. ACS Catalysis, Vol. 7, Issue 3 https://doi.org/10.1021/acscatal.6b02707	journal	February 2017
Regio- and stereoselective intermolecular phenol coupling enzymes in secondary metabolite biosynthesis Hüttel, Wolfgang; Müller, Michael Natural Product Reports, Vol. 38, Issue 5 https://doi.org/10.1039/d0np00010h	journal	January 2021
Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination Barrett, Kimberly T.; Miller, Scott J. Journal of the American Chemical Society, Vol. 135, Issue 8 https://doi.org/10.1021/ja400082x	journal	February 2013
Regioselective Derivatizations of a Tribrominated Atropisomeric Benzamide Scaffold Barrett, Kimberly T.; Miller, Scott J. Organic Letters, Vol. 17, Issue 3 https://doi.org/10.1021/ol503593y	journal	January 2015
Atropisomers beyond the C–C axial chirality: Advances in catalytic asymmetric synthesis Mei, Guang-Jian; Koay, Wai Lean; Guan, Chun-Yan Chem, Vol. 8, Issue 7 https://doi.org/10.1016/j.chempr.2022.04.011	journal	July 2022
Directed Evolution of RebH for Site-Selective Halogenation of Large Biologically Active Molecules Payne, James T.; Poor, Catherine B.; Lewis, Jared C. Angewandte Chemie International Edition, Vol. 54, Issue 14 https://doi.org/10.1002/anie.201411901	journal	February 2015
Specific Enzymatic Halogenation-From the Discovery of Halogenated Enzymes to Their Applications In Vitro and In Vivo Weichold, Veit; Milbredt, Daniela; van Pée, Karl-Heinz Angewandte Chemie International Edition, Vol. 55, Issue 22 https://doi.org/10.1002/anie.201509573	journal	April 2016
Cytochrome P450-Catalyzed Regio- and Stereoselective Phenol Coupling of Fungal Natural Products Mazzaferro, Laura S.; Hüttel, Wolfgang; Fries, Alexander Journal of the American Chemical Society, Vol. 137, Issue 38 https://doi.org/10.1021/jacs.5b06776	journal	September 2015
Highly accurate protein structure prediction with AlphaFold Jumper, John; Evans, Richard; Pritzel, Alexander Nature https://doi.org/10.1038/s41586-021-03819-2	journal	July 2021
Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer Burns, Noah Z.; Krylova, Irina N.; Hannoush, Rami N. Journal of the American Chemical Society, Vol. 131, Issue 26 https://doi.org/10.1021/ja903745s	journal	June 2009
Discovery of 6-Fluoro-5-( R )-(3-( S )-(8-fluoro-1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4 H )-yl)-2-methylphenyl)-2-( S )-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1 H -carbazole-8-carboxamide (BMS-986142): A Reversible Inhibitor of Bruton’s Tyrosine Kinase (BTK) Conformationally Constrained by Two Locked Atropisomers Watterson, Scott H.; De Lucca, George V.; Shi, Qing Journal of Medicinal Chemistry, Vol. 59, Issue 19 https://doi.org/10.1021/acs.jmedchem.6b01088	journal	September 2016
Regioselective Arene Halogenation using the FAD-Dependent Halogenase RebH Payne, James T.; Andorfer, Mary C.; Lewis, Jared C. Angewandte Chemie International Edition, Vol. 52, Issue 20 https://doi.org/10.1002/anie.201300762	journal	April 2013
Enzymatic approaches for the preparation of optically active non-centrochiral compounds Skrobo, Benedikt; Rolfes, Julian D.; Deska, Jan Tetrahedron, Vol. 72, Issue 10 https://doi.org/10.1016/j.tet.2016.01.026	journal	March 2016
Directed evolution of RebH for catalyst-controlled halogenation of indole C–H bonds Andorfer, Mary C.; Park, Hyun June; Vergara-Coll, Jaylie Chemical Science, Vol. 7, Issue 6 https://doi.org/10.1039/c5sc04680g	journal	January 2016
New Insights into the Mechanism of Enzymatic Chlorination of Tryptophan Flecks, Silvana; Patallo, Eugenio P.; Zhu, Xiaofeng Angewandte Chemie International Edition, Vol. 47, Issue 49 https://doi.org/10.1002/anie.200802466	journal	November 2008
The structure of flavin-dependent tryptophan 7-halogenase RebH Bitto, Eduard; Huang, Yu; Bingman, Craig A. Proteins: Structure, Function, and Bioinformatics, Vol. 70, Issue 1 https://doi.org/10.1002/prot.21627	journal	September 2007
Flavin-dependent halogenases catalyze enantioselective olefin halocyclization Mondal, Dibyendu; Fisher, Brian F.; Jiang, Yuhua Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-23503-3	journal	June 2021
Structural Insights from Molecular Dynamics Simulations of Tryptophan 7-Halogenase and Tryptophan 5-Halogenase Ainsley, Jon; Mulholland, Adrian J.; Black, Gary W. ACS Omega, Vol. 3, Issue 5 https://doi.org/10.1021/acsomega.8b00385	journal	May 2018
AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading Trott, Oleg; Olson, Arthur J. Journal of Computational Chemistry https://doi.org/10.1002/jcc.21334	journal	January 2009
Synthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross-Coupling Gustafson, Jeffrey L.; Lim, Daniel; Barrett, Kimberly T. Angewandte Chemie International Edition, Vol. 50, Issue 22 https://doi.org/10.1002/anie.201101147	journal	April 2011
Understanding and Improving the Activity of Flavin-Dependent Halogenases via Random and Targeted Mutagenesis Andorfer, Mary C.; Lewis, Jared C. Annual Review of Biochemistry, Vol. 87, Issue 1 https://doi.org/10.1146/annurev-biochem-062917-012042	journal	June 2018
Robust in vitro activity of RebF and RebH, a two-component reductase/halogenase, generating 7-chlorotryptophan during rebeccamycin biosynthesis Yeh, E.; Garneau, S.; Walsh, C. T. Proceedings of the National Academy of Sciences, Vol. 102, Issue 11 https://doi.org/10.1073/pnas.0500755102	journal	March 2005
Site-Selective C–H Halogenation Using Flavin-Dependent Halogenases Identified via Family-Wide Activity Profiling Fisher, Brian F.; Snodgrass, Harrison M.; Jones, Krysten A. ACS Central Science, Vol. 5, Issue 11 https://doi.org/10.1021/acscentsci.9b00835	journal	September 2019
Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination Diener, Matthew E.; Metrano, Anthony J.; Kusano, Shuhei Journal of the American Chemical Society, Vol. 137, Issue 38 https://doi.org/10.1021/jacs.5b07726	journal	September 2015
Illuminating the dark conformational space of macrocycles using dominant rotors Diaz, Diego B.; Appavoo, Solomon D.; Bogdanchikova, Anastasia F. Nature Chemistry, Vol. 13, Issue 3 https://doi.org/10.1038/s41557-020-00620-y	journal	February 2021
Halogenases: powerful tools for biocatalysis (mechanisms applications and scope) Gkotsi, Danai S.; Dhaliwal, Jag; McLachlan, Matthew MW Current Opinion in Chemical Biology, Vol. 43 https://doi.org/10.1016/j.cbpa.2018.01.002	journal	April 2018
Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies Carmona, José A.; Rodríguez-Franco, Carlos; Fernández, Rosario Chemical Society Reviews, Vol. 50, Issue 5 https://doi.org/10.1039/d0cs00870b	journal	January 2021
Peptide-Based Catalysts Reach the Outer Sphere through Remote Desymmetrization and Atroposelectivity Metrano, Anthony J.; Miller, Scott J. Accounts of Chemical Research, Vol. 52, Issue 1 https://doi.org/10.1021/acs.accounts.8b00473	journal	December 2018
Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis Toste, F. Dean; Sigman, Matthew S.; Miller, Scott J. Accounts of Chemical Research, Vol. 50, Issue 3 https://doi.org/10.1021/acs.accounts.6b00613	journal	March 2017
Development of Halogenase Enzymes for Use in Synthesis Latham, Jonathan; Brandenburger, Eileen; Shepherd, Sarah A. Chemical Reviews, Vol. 118, Issue 1 https://doi.org/10.1021/acs.chemrev.7b00032	journal	May 2017
4(3H)-Quinazolinone derivatives: Promising antibacterial drug leads Gatadi, Srikanth; Lakshmi, T. Vasanta; Nanduri, Srinivas European Journal of Medicinal Chemistry, Vol. 170 https://doi.org/10.1016/j.ejmech.2019.03.018	journal	May 2019
Biocatalytic oxidative cross-coupling reactions for biaryl bond formation Zetzsche, Lara E.; Yazarians, Jessica A.; Chakrabarty, Suman Nature, Vol. 603, Issue 7899 https://doi.org/10.1038/s41586-021-04365-7	journal	March 2022
Biocatalytic synthesis of planar chiral macrocycles Gagnon, Christina; Godin, Éric; Minozzi, Clémentine Science, Vol. 367, Issue 6480 https://doi.org/10.1126/science.aaz7381	journal	February 2020
Assessing Atropisomer Axial Chirality in Drug Discovery and Development LaPlante, Steven R.; Fader, Lee D.; Fandrick, Keith R. Journal of Medicinal Chemistry, Vol. 54, Issue 20 https://doi.org/10.1021/jm200584g	journal	September 2011
Enantioselective Desymmetrization of Methylenedianilines via Enzyme-Catalyzed Remote Halogenation Payne, James T.; Butkovich, Paul H.; Gu, Yifan Journal of the American Chemical Society, Vol. 140, Issue 2 https://doi.org/10.1021/jacs.7b09573	journal	January 2018

Similar Records

Flavin-dependent halogenases catalyze enantioselective olefin halocyclization

Journal Article · 2021 · Nature Communications · OSTI ID:1785405

The structure of flavin-dependent tryptophan 7-halogenase RebH

Journal Article · 2007 · Proteins · OSTI ID:1485646

Related Subjects

Chemistry

Directed Evolution of Flavin-Dependent Halogenases for Site- and Atroposelective Halogenation of 3-Aryl-4(3 H )-Quinazolinones via Kinetic or Dynamic Kinetic Resolution

Citation Formats

References (42)

Similar Records

Related Subjects