Publications

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*corresponding author #undergraduate researcher


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77
Identifying and Engineering Flavin Dependent Halogenases for Selective Biocatalysis

Lewis, J. C.* Identifying and Engineering Flavin-Dependent Halogenases for Selective Biocatalysis, submitted

Preprint available on ChemRxiv.

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Category: Biocatalysis

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76
Selective C-H Halogenation of Alkenes and Alkynes Using Flavin-Dependent Halogenases

Jiang, Y.; Kim, A.; Olive, C.; Lewis, J. C.* Selective C-H Halogenation of Alkenes and Alkynes Using Flavin-Dependent Halogenases. Angew. Chem. Int. Ed., accepted

Original preprint available on ChemRxiv.

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Category: Biocatalysis

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75
Non-Native Intramolecular Radical Cyclization Catalyzed by a B12-Dependent Enzyme

Li, J.; Kumar, A.; Lewis, J. C.* Non-Native Intramolecular Radical Cyclization Catalyzed by a B12-Dependent Enzyme. Angew. Chem. Int. Ed., 2023, e202312893.

Original preprint available on ChemRxiv.

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Category: Biocatalysis

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74
Non-Native Site-Selective Enzyme Catalysis

Mondal, D.; Snodgrass, H. M.; Gomez, C. A.; Lewis, J. C.* Chem. Rev. 2023, 123, 10381-10431.

See the original preprint available on ChemRxiv.

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Category: Artificial Metalloenzymes | Biocatalysis

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72
Asymmetric Catalysis by Flavin Dependent Halogenases

Jiang, Y.; Lewis, J. C.* Chirality, 2023, 1-9.

See the original manuscript on ChemRxiv.

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Category: Biocatalysis

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71
First and Second Sphere Interactions Accelerate Non-Native N-Alkylation Catalysis by the Thermostable, Methanol-Tolerant B12-Dependent Enzyme MtaC.

Kumar, A.; Yang, X., Li, J.; Lewis, J. C.* ChemComm, 2023, 59, 4798-4801.

See the original preprint on ChemRxiv.

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Category: Biocatalysis | Organometallics

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70
Directed Evolution of a Fe(II)- and alpha-Ketoglutarate-Dependent Dioxygenase for Site-Selective Azidation of Unactivated Aliphatic C-H Bonds

Gomez, C.; Mondal, D.; Du, Q.; Chan, N.; Lewis, J. C.* Angew. Chem. Int. Ed. 2023,  e202301370.

See the original manuscript on ChemRxiv.

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Category: Biocatalysis

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69
The Single Component Flavin Reductase/Flavin Dependent Halogenase AetF is a Versatile Catalyst for Selective Bromination and Iodination of Arenes and Olefins

Jiang, Y.; Snodgrass, H. M.; Zubi, Y. S.; Roof, C. V.; Guan, Y.; Mondal, D.; Honeycutt, N. H.#; Lee, J.; Lewis, R. D.; Martinez, C. A.; Lewis, J. C.* Angew. Chem. Int. Ed. 2022, 61, e202214610.

See the original manuscript on ChemRxiv.

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Category: Biocatalysis

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68
Expanding the Reactivity of Flavin Dependent Halogenases Toward Olefins via Enantioselective Intramolecular Haloetherification and Chemoenzymatic Oxidative Rearrangements

Jiang, Y.; Mondal, D.; Lewis, J. C.* ACS Catalysis, 202212, 13501-13505. Check out the original manuscript on ChemRxiv.

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Category: Biocatalysis

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67
Non-native Anionic Ligand Binding and Reactivity in Engineered Variants of the Fe(II)- and α-Ketoglutarate-Dependent Oxygenase, SadA

Chan, N. H.; Gomez, C.; Vennelakanti, V.; Du, Q.; Kulik, H. J.*; Lewis, J. C.* Inorg. Chem. 202261, 14477-14485. Check out the original manuscript on ChemRxiv.

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Category: Biocatalysis

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65
Directed Evolution of Flavin-Dependent Halogenases for Atroposelective Halogenation of 3-Aryl-4(3H)-quinazolinones via Kinetic or Dynamic Kinetic Resolution

Snodgrass, H. M.; Mondal, D.; Lewis, J. C.* J. Am. Chem. Soc. 2022144, 16676-16682.. See the original manuscript on ChemRxiv.

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Category: Biocatalysis

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64
Analysis of Laboratory-Evolved Flavin-Dependent Halogenases Affords a Computational Model for Predicting Halogenase Site Selectivity

Andorfer, M. C.; Evans, D.; Yang, S. He, C. Q.; Girlich, A. M.#; Vergara-Coll, J.#; Sukumar, N.; Houk, K. N.*; Lewis, J. C.* Chem. Catal. 2022, 2, 2658-2674. Check out the original manuscript on ChemRxiv.

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Category: Biocatalysis

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63
Metal-Responsive Regulation of Enzyme Catalysis Using Genetically Encoded Chemical Switches

Zubi, Y. S.; Seki, K.; Li, Y.; Hunt, A.; Liu, B.; Roux, B.*, Jewett, M. C.*, Lewis, J. C.* Nat. Commun. 2022, 13, 1864. Preprint available on ChemRxiv. See peer review here.

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Category: Artificial Metalloenzymes | Biocatalysis | Chemical Biology

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61
Controlling Non-Native B12 Reactivity and Catalysis in the Transcription Factor CarH

Yang, X.; Gerroll, B. H. R.; Jiang, Y.; Kumar, A.; Zubi, Y. S.; Baker, L. A.; Lewis, J. C.* ACS Catal. 2022, 12, 935-942. Preprint available on ChemRxiv.

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Category: Biocatalysis | Organometallics

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60
Phage-Assisted Continuous Evolution and Selection of Enzymes for Chemical Synthesis

Jones, K. A.; Snodgrass, H. M.; Belsare, K.; Dickinson, B. C.*, Lewis, J. C.* ACS Central Science, 2021, 7, 1581-1590. Preprint available on ChemRxiv.

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Category: Biocatalysis | Chemical Biology

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58
Flavin-Dependent Halogenases Catalyze Enantioselective Olefin Halocyclization.

Dibyendu Mondal, Brian F. Fisher, Yuhua Jiang, Jared C. Lewis*. Flavin-Dependent Halogenases Catalyze Enantioselective Olefin Halocyclization. Nat. Commun. 2021, 3268. You can read the original manuscript at ChemRxiv. See peer review discussion here.

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Category: Biocatalysis

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55
A High-throughput Method for Directed Evolution of NAD(P)+ dependent Dehydrogenases for the Reduction of Biomimetic Nicotinamide Analogues

Huang, R.; Chen, H.; Upp, D. M.; Lewis, J. C.; Zhang, Y.-H. P. J.* A High-throughput Method for Directed Evolution of NAD(P)+-dependent Dehydrogenases for the Reduction of Biomimetic Nicotinamide Analogues. ACS Catalysis, 2019, 9, 11709.

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Category: Biocatalysis

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53
Site-Selective C-H Halogenation using Flavin-Dependent Halogenases Identified via Family-Wide Activity Profiling

Fisher, B. F.; Snodgrass, H. M.; Jones, K. A.; Andorfer, M. C.; Lewis, J. C.* Site-Selective C-H Halogenation using Flavin-Dependent Halogenases Identified via Family-Wide Activity Profiling. ACS Central Science, 2019, 11, 1184. See the original manuscript at ChemRxiv.

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Category: Biocatalysis

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49
Pyrococcus furiosus Prolyl Oligopeptidase: A Dynamic Supramolecular Host for Peptidase and Dirhodium Catalysis

Ellis-Guardiola, K.; Rui, H.; Beckner, R.;# Srivastava, P.; Sukumar, N.*; Roux, B.*; Lewis, J. C.* Crystal Structure and Conformational Dynamics of Pyrococcus furiosus Prolyl Oligopeptidase. Biochemistry2019, 58, 1616.

The studies detailed in this manuscript were originally reported on ChemRxiv. The ChemRxiv manuscript detailed how the large scale conformational dynamics outlined in the Biochemistry paper can be used to rationalize the specificity of dirhodium ArMs created from the POP scaffold for cyclopropanation over water O-H insertion. Unfortunately, we were unable to convince reviewers of the latter point, but you can still read about it on ChemRxiv here!

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Category: Artificial Metalloenzymes | Biocatalysis

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48
Enantioselective Desymmetrization of Methylenedianilines via Enzyme-Catalyzed Remote Halogenation

Payne, J. T.; Butkovich, P.; Kunze, K. N.#; Park, H.-J.; Yang, D.-S.; Lewis, J. C.* Enantioselective Desymmetrization of Methylenedianilines via Enzyme-Catalyzed Remote Halogenation. J. Am. Chem. Soc. 2018, 140, 546-549.

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Category: Biocatalysis

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45
Understanding and Improving the Activity of Flavin Dependent Halogenases via Random and Targeted Mutagenesis

Andorfer, M. C.; Lewis, J. C.* Understanding and Improving the Activity of Flavin Dependent Halogenases via Random and Targeted Mutagenesis. Ann. Rev. Biochem. 2018, 87, 159-185.

Category: Biocatalysis

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42
Aromatic Halogenation Using Bifunctional Flavin Reductase-Halogenase Fusion Enzymes

Andorfer, M. C.; Belsare, K. D.; Girlich, A. M.#; Lewis, J. C.* Aromatic Halogenation Using Bifunctional Flavin Reductase-Halogenase Fusion Enzymes.  ChemBioChem, 2017, 18, 2099-2103.

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Category: Biocatalysis

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40
Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling

Andorfer, M. C.; Grob, J. E.; Hajdin, C. E.; Chael, J. R.#; Siuti, P.; Lilly, J.; Tan, K. L.*; Lewis, J. C.* Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling. ACS Catalysis. 2017, 7, 1897-1904.

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39
A Simple Combinatorial Codon Mutagenesis Method for Targeted Protein Engineering

Belsare, K.; Andorfer, M. C.; Cardenas, F.#; Chael, J. R.#; Park, H. J.; Lewis, J. C.* A Simple Combinatorial Codon Mutagenesis Method for Targeted Protein Engineering. ACS Synth. Biol. 2017, 6, 416-420.

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37
Engineering Flavin-Dependent Halogenases

Payne, J. T.; Andorfer, M. C.; Lewis, J. C.* Engineering Flavin-Dependent Halogenases. Meth. Enz. 2016, 575, 93-126.

Category: Biocatalysis

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36
Directed Evolution of RebH for Catalyst-Controlled Halogenation of Indole C-H Bonds

Andorfer, M. C.; Park, H. J.; Vergara-Coll, J.#; Lewis, J. C.* Directed Evolution of RebH for Catalyst-Controlled Halogenation of Indole C-H Bonds. Chem. Sci. 2016, 7, 3720-3729.

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35
Late-Stage Diversification of Biologically Active Molecules via Chemoenzymatic C-H Functionalization

Durak, L. J.; Payne, J. T.; Lewis, J. C.* Late-Stage Diversification of Biologically Active Molecules via Chemoenzymatic C-H Functionalization. ACS Catal. 2016, 6, 1451-1454.

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Category: Biocatalysis

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32
Directed Evolution of RebH for Site Selective Halogenation of Large, Biologically Active Molecules

Payne, J. T.; Poor, C. B.; Lewis, J. C.* Directed Evolution of RebH for Site Selective Halogenation of Large, Biologically Active Molecules. Angew. Chem. Int. Ed. 2015, 54, 4226.

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See a Synfacts comment here.

Category: Biocatalysis

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30
Improving the Stability of the FAD-Dependent Halogenase RebH Using Directed Evolution

Poor, C. B.; Andorfer, M. C.; Lewis, J. C.* Improving the Stability of the FAD-Dependent Halogenase RebH Using Directed Evolution.  ChemBioChem. 2014, 15, 1286-1289.

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28
Upgrading Nature’s Tools: Expression Enhancement and Preparative Utility of the Halogenase RebH

Payne, J. T.; Lewis, J. C.* Upgrading Nature’s Tools: Expression Enhancement and Preparative Utility of the Halogenase RebH. Synlett 2014, 25, 1345-1349.

Category: Biocatalysis

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23
Regioselective Arene Halogenation Using the FAD-Dependent Halogenase RebH

Payne, J. T.; Andorfer, M. C.; Lewis, J. C. Regioselective Arene Halogenation Using the FAD-Dependent Halogenase RebH. Angew. Chemie. Int. Ed. 2013, 125, 5379-5382.

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21
Enantioselective Intramolecular C-H amination Catalysed by Engineered Cytochrome P450 Enzymes in vitro and in vivo

McIntosh, J. A.; Coelho, P. S.; Farwell, C. C.; Wang, Z. J.; Lewis, J. C.; Brown, T. R.#; Arnold, F. H.* Enantioselective Intramolecular C-H amination Catalysed by Engineered Cytochrome P450 Enzymes in vitro and in vivo. Angew. Chem. Int. Ed. 2013, 52, 9309 –9312.

Category: Biocatalysis

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20
Synthetic Biology Approaches for Organic Synthesis

“Synthetic Biology Approaches for Organic Synthesis,” P. S. Coelho, J. C. Lewis, F. H. Arnold.* Article 00931 in Comprehensive Organic Synthesis II. G. Molander and P. Knochel (Eds.), Elsevier Ltd: Oxford. 2014, 390-420.

Category: Biocatalysis

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19
Enzymatic Functionalization of Carbon-Hydrogen Bonds

Lewis, J. C.; Coelho, P. S.; Arnold, F. H.* Enzymatic Functionalization of Carbon-Hydrogen Bonds. Chem. Soc. Rev. 2011, 40, 2003-2021.

Category: Biocatalysis

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18
Combinatorial Alanine Substitution Enables Rapid Optimization of Cytochrome P450BM3 for Selective Hydroxylation of Large Substrates

Lewis, J. C.; Mantovani, S. M.; Fu, Y.; Snow, C. D.; Komor, R. S.; Wong, C. H.; Arnold, F. H.* Combinatorial Alanine Substitution Enables Rapid Optimization of Cytochrome P450BM3 for Selective Hydroxylation of Large Substrates. ChemBioChem. 2010, 11, 2502-2505.

Category: Biocatalysis

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17
Chemoenzymatic Elaboration of Monosaccharides Using Engineered Cytochrome P450 BM-3 Demethylases

Lewis, J. C.; Bastian, S.; Bennett, C. S.; Fu, Y.; Mitsuda, Y.; Chen, M. M.; Greenberg, W. A.; Wong, C.-H.; Arnold, F. H.* Chemoenzymatic Elaboration of Monosaccharides Using Engineered Cytochrome P450 BM-3 Demethylases. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 16550-16555.

Category: Biocatalysis

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16
Catalysts on Demand: Selective Oxidations by Laboratory-Evolved Cytochrome P450 BM-3

Lewis, J. C.; Arnold, F. H.* Catalysts on Demand: Selective Oxidations by Laboratory-Evolved Cytochrome P450 BM-3. Chimia 2009, 63, 309-312.

Category: Biocatalysis

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Patents

3    Coelho, Pedro, S.; Brustad, Eric M.; Arnold, Frances H.; Wang, Z.; Lewis, Jared C. In vivo and in vitro olefin cyclopropanation catalyzed by engineered and chimeric heme enzyme.” PCT Int. Appl. WO2014058744, 2014.

2    Arnold, F. H.; Wong, C.-H.; Mitsuda, Y.; Chen, M. M.; Bennett, C. S.; Greenberg, W. A.; Lewis, J. C.; Bastian, S. Engineered Bacterial Cytochrome P450 Variants for Preparation of Selectively Protected Carbohydrates. Patent No. US 20090124515, 2009.

1    Collins, C. A.; Gao, J.; Kym, P. R.; Lewis, J. C.; Souers, A. J.; Vasudevan, A.; Wodka, D. 2-Aminoquinolones as Melanin Concentrating Hormone Receptor Antagonists. Patent No. WO 2003105850, 2003.