Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

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 · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/jacs.2c07422· OSTI ID:1982067

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, Vol. 144, Issue 36; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English

References (39)

Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis journal March 2017
Illuminating the dark conformational space of macrocycles using dominant rotors journal February 2021
Recent advances and new concepts for the synthesis of axially stereoenriched biaryls journal January 2015
Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products journal February 2011
Assessing Atropisomer Axial Chirality in Drug Discovery and Development journal September 2011
Discovery of a Covalent Inhibitor of KRAS G12C (AMG 510) for the Treatment of Solid Tumors journal December 2019
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 journal September 2016
Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer journal June 2009
Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies journal January 2021
Atropisomers beyond the C–C axial chirality: Advances in catalytic asymmetric synthesis journal July 2022
Enzymatic approaches for the preparation of optically active non-centrochiral compounds journal March 2016
Biocatalytic synthesis of planar chiral macrocycles journal February 2020
Cytochrome P450-Catalyzed Regio- and Stereoselective Phenol Coupling of Fungal Natural Products journal September 2015
Biocatalytic oxidative cross-coupling reactions for biaryl bond formation journal March 2022
Peptide-Based Catalysts Reach the Outer Sphere through Remote Desymmetrization and Atroposelectivity journal December 2018
Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination journal February 2013
Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination journal September 2015
Synthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross-Coupling journal April 2011
Dynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Asymmetric Bromination journal June 2010
Regioselective Derivatizations of a Tribrominated Atropisomeric Benzamide Scaffold journal January 2015
Directed Evolution of RebH for Site-Selective Halogenation of Large Biologically Active Molecules journal February 2015
Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling journal February 2017
Site-Selective C–H Halogenation Using Flavin-Dependent Halogenases Identified via Family-Wide Activity Profiling journal September 2019
Development of Halogenase Enzymes for Use in Synthesis journal May 2017
Specific Enzymatic Halogenation-From the Discovery of Halogenated Enzymes to Their Applications In Vitro and In Vivo journal April 2016
Halogenases: powerful tools for biocatalysis (mechanisms applications and scope) journal April 2018
Enantioselective Desymmetrization of Methylenedianilines via Enzyme-Catalyzed Remote Halogenation journal January 2018
Flavin-dependent halogenases catalyze enantioselective olefin halocyclization journal June 2021
New Insights into the Mechanism of Enzymatic Chlorination of Tryptophan journal November 2008
Structural Insights from Molecular Dynamics Simulations of Tryptophan 7-Halogenase and Tryptophan 5-Halogenase journal May 2018
Analysis of laboratory-evolved flavin-dependent halogenases affords a computational model for predicting halogenase site selectivity journal October 2022
Development of α-glucosidase inhibitors by room temperature C–C cross couplings of quinazolinones journal January 2013
Highly accurate protein structure prediction with AlphaFold journal July 2021
Understanding and Improving the Activity of Flavin-Dependent Halogenases via Random and Targeted Mutagenesis journal June 2018
The structure of flavin-dependent tryptophan 7-halogenase RebH journal September 2007
Robust in vitro activity of RebF and RebH, a two-component reductase/halogenase, generating 7-chlorotryptophan during rebeccamycin biosynthesis journal March 2005
Regioselective Arene Halogenation using the FAD-Dependent Halogenase RebH journal April 2013
4(3H)-Quinazolinone derivatives: Promising antibacterial drug leads journal May 2019
Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts journal May 2017