Publications

65. Yang, D., Chiang, C-H., Wititsuwannakul, T., Brooks, C. L. III, Zimmerman, P. M., Narayan, A. R. H.* "Engineering the Reaction Pathway of a Non-heme Iron Oxygenase Using Ancestral Sequence Reconstruction", J. Am. Chem. Soc. 2024 DOI: 10.1021/jacs.4c08420

graphical abstract

64. Paton, A., Boiko, D., Perkins, J., Cemalovic, N., Reschützegger, T., Gomes, G., Narayan, A. R. H.* "Generation of connections between protein sequence space and chemical space to enable a predictive model for biocatalysis", ChemRxiv. 2024 DOI: 10.26434/chemrxiv-2024-w4dtr

63. Chiang, C.-H.; Wang, Ye.; Hussain, A.; Brooks, C. L. III*; Narayan, A. R. H.* "Ancestral Sequence Reconstruction to Enable Biocatalytic Synthesis of Azaphilones", J. Am. Chem. Soc. 2024, 146 (33), 23321-23329. DOI: 10.1021/jacs.4c08761

graphical abstract

62. Wang, Y.; Das, S.; Aboulhosn, K.; Champagne, S. E.; Gemmel, P. M.; Skinner, K. C.; Ragsdale, S.W.; Zimmerman, P. M.; Narayan, A. R. H.* "Nature-Inspired Radical Pyridoxal-Mediated C–C Bond Formation", J. Am. Chem. Soc. 2024, 146 (33), 23321-23329. DOI: 10.1021/jacs.4c05997 (First available on ChemRxiv, DOI: 10.26434/chemrxiv-2024-s18q5)

graphical abstract

61. Wang, Y.; Torma, K.J.; Pyser, J.B.; Zimmerman, P.; Narayan, A. R. H.*; "Substrate-selective catalysis enabled synthesis of azaphilone natural products", ACS Cent. Sci. 2024, 10 (3), 708-716. DOI: 10.1021/acscentsci.3c01405 (First available on ChemRxiv, DOI: 10.26434/chemrxiv-2023-nkbn0)

graphical abstract

60. Champagne, S. E.; Chiang, C.-H.; Gemmel, P. M.; Brooks, C. L. III; Narayan, A. R. H.*; "Biocatalytic Stereoselective Oxidation of 2-Arylindoles", J. Am. Chem. Soc. 2024, 146 (4), 2728-2735. DOI: 10.1021/jacs.3c12393

graphical abstract

59. Skinner, K. C.; Kammeraad, J. A.; Wymore, T.; Narayan, A. R. H.; Zimmerman, P. M.*; "Simulating Electron Transfer Reactions in Solution: Radical-Polar Crossover", J. Phys. Chem. B. 2023, 127 (47), 10097–10107. DOI: 10.1021/acs.jpcb.3c06120

J. Phys. Chem. B. graphical abstract

58. Makey, D. M.; Diehl, R. C.; Xin, Y.; Murray, B. E.; Stoll, D. R.; Ruotolo, B. T.; Grinias, J. P.; Narayan, A. R. H.; Lopez-Carillo, V.; Stark, M.; Johnen, P.; Kennedy, R. T.*; "High-Throughput Liquid Chromatographic Analysis Using a Segmented Flow Injector with a 1 s Cycle Time", Anal. Chem. 2023, 95 (46), 17028–17036. DOI: 10.1021/acs.analchem.3c03719

anal. chem. graphical abstract

57. Roos, C. B.; Chiang, C.-H.; Murray, L. A. M.; Yang, D.; Schulert, L.; Narayan, A. R. H.*; "Stereodynamic Strategies to Induce and Enrich Chirality of Atropisomers at a Late Stage", Chem. Rev. 2023, 123 (17), 10641–10727. DOI: 10.1021/acs.chemrev.3c00327

graphical abstract

56. Romero, E.O.; Saucedo, A.T.; Hernández-Meléndez, J.R.; Yang, D.; Chakrabarty, S.; Narayan, A. R. H.*; "Enabling Broader Adoption of Biocatalysis in Organic Chemistry", ACS AU. 2023, 3 (8), 2073–2085. DOI: 10.1021/jacsau.3c00263

graphical abstract

55. Perkins, J.C.‡; Golliher, A.E.‡; Hernández-Meléndez, J.R.; Saucedo, A.T.; Doyon, T.J.; Narayan, A. R. H.*; "Enzyme Library-enabled Chemoenzymatic Tropolone Synthesis", (preprint) ChemRxiv. 2023 DOI: 10.26434/chemrxiv-2023-lvngd

‡ These authors contributed equally.

graphical abstract

54. Chiang, C.-H.; Wymore, T.; Benitez, A. R.; Hussain, A.; Smith, J. L.; Brooks, C. L. III; Narayan, A. R. H.*; "Deciphering the evolution of flavin-dependent monooxygenase stereoselectivity using ancestral sequence reconstruction", PNAS. 2023, 120, e2218248120 DOI: 10.1073/pnas.2218248120

graphical abstract

53. Romero, E. O.; Perkins, J. C.; Burch, J.E.; Delgadillo, D.A.; Nelson, H. M.; Narayan, A. R. H.*; "Chemoenzymatic Synthesis of (+)-Xyloketal B", Org. Lett. 2023, 25, 1547–1552 DOI: 10.1021/acs.orglett.3c00334

graphical abstract - chemoenzymatic synthesis of xyloketal B

52. Zetzsche, L. E.; Chakrabarty, S.; Narayan, A. R. H.*; "Development of a P450 Fusion Enzyme for Biaryl Coupling in Yeasts", ACS Chem. Bio. 2022, 17, 2986–2992 DOI: 10.1021/acschembio.2c00690

51. Ackenhusen, S.E.; Wang, Y.; Chun, S. W.; Narayan, A. R. H.*; "Understanding and Circumventing the Requirement for Native Thioester Substrates for α-Oxoamine Synthase Reactions", ACS Chem. Bio. 2022, 17, 2389–2395 DOI: 10.1021/acschembio.2c00365  (first available on ChemRxiv, DOI: 10.26434/chemrxiv.14535282.v1)

50. Lao, Y; Skiba, M. A.; Chun, S. W.; Narayan, A. R. H. Smith, J. L.;* "Structural Basis for Control of Methylation Extent in Polyketide Synthase Metal-Dependent C-Methyltransferases", ACS Chem. Bio. 2022, 17, 2088–2098 DOI: 10.1021/acschembio.2c00085

49. Zetzsche, L. E.; Chakrabarty, S.; Narayan, A. R. H.* "The Transformative Power of Biocatalysis in Convergent Synthesis," J. Am. Chem. Soc. 2022, 144 (12), 5214-5225. DOI:10.1021/jacs.2c0022

48. Zetzsche, L. E.‡; Yazarians, J. A.‡; Chakrabarty, S.; Hinze, M. E.; Murray, L. A. M.; Lukowski, A. L.; Joyce, L. A.; Narayan, A. R. H.* "Biocatalytic oxidative cross-coupling reactions for biaryl bond formation," Nature 2022, 603, 79-85. DOI: 10.1038/s41586-021-04365-7
(first available on ChemRxiv, DOI: 10.33774/chemrxiv-2021-v0bv6-v2)
        ‡ These authors contributed equally.

 

47.  Liu, J.; Tian, J.; Perry, C.; Lukowski, A. L.; Doukov, T. I.; Narayan, A. R. H.*; Bridwell-Rabb, J.* "Design Principles for Site-Selective Hydroxylation by a Rieske Oxygenase" Nat. Commun. 2022, 13, 255. DOI: 10.1038/s41467-021-27822-3

45. Pyser, J. B.; Chakrabarty, S.; Evan, E. O.; Narayan, A. R. N.* “State-of-the-art biocatalysis” ACS Cent. Sci. 2021, 7 (7), 1105-1116. DOI: 10.1021/acscentsci.1c00273

44. Chakrabraty, S.; Romero, E. O.; Pyser, J. B.; Yazarians, J. A.; Narayan, A. R. H.* “Chemoenzymatic Total Synthesis of Natural Products” Acc. Chem. Res. 2021, 54, 1374-1384. DOI: 10.1021/acs.accounts.0c00810

43. Doyon, T. J; Skinner, K. C.; Yang, D.; Mallik, L.; Wymore, T.; Koutmos, M.; Zimmerman, P. M; Narayan, A. R. H. "Radical tropolone biosynthesis" ChemRxiv 2020, DOI:10.26434/chemrxiv.12780044.

42. Chakrabarty, S.; Wang, Y.; Perkins, J. C.; Narayan, A. R. H. "Scalable Biocatalytic C–H Oxyfunctionalization Reactions" Chem. Soc. Rev. 2020, 49, 8137-8155. DOI: 10.1039/d0cs00440e.

41. Chun, S. W. and Narayan, A. R. H. "Biocatalytic, Stereoselective Deuteration of α-Amino Acids and Methyl Esters" ACS Catal. 2020, 10 (13), 7413-7418. DOI: 10.1021/acscatal.0c01885.

40. Lukowski, A. L.;‡ Liu, J.;‡ Bridwell-Rabb, J.;* Narayan, A. R. H.* "Structural basis for divergent C–H hydroxylation selectivity in two Rieske oxygenases" Nat. Commun. 2020, 11 (2991) DOI: 10.1038/38/s41467-020-16729-0.

        ‡ These authors contributed equally.

39. Baker Dockrey, S. A. and Narayan, A. R. H. "Photocatalytic oxidative dearomatization of orcinaldehyde derivatives" Org. Lett. 2020 DOI: 10.1021.acs.orglett.0c01207.

38. Zetzsche, L. E. and Narayan, A. R. H. "Broadening the scope of biocatalytic C–C bond formation" Nat. Rev. Chem. 2020 DOI:10.1038/s41570-020-0191-2.

37. Rodríguez Benítez, A.; Dürr, S. L.; Narayan, A. R. H. "Radial scope: A new visualization tool for structure-data relationships" Trends in Chemistry 2020, DOI: https://doi.org/10.1016/j.trechm.2020.04.003.

36. Denomme, N.; Lukowski, A. L.; Hull, J. M.; Jameson, M. B.; Bouxa, A. A.; Narayan, A. R. H.; Isom, L. L. Neurosci. Lett. 2020, 724, 134853. DOI: j.neulet.2020.134853

35. Lukowski, A. L.; Mallik, L.; Hinze, M. E.; Carlson, B. M.; Ellinwood, D. C.; Pyser, J. B.; Koutmos, M. and Narayan, A. R. H. "Substrate promiscuity of a paralytic shellfish toxin amidinotransferase" ACS Chem. Biol. 2020, 15, DOI: 10.1021/acschembio.9b00964.

34. Doyon, T. J.; Perkins, J. C.; Baker Dockrey, S. A.; Skinner, K. C.; Zimmerman, P. M.; Narayan, A. R. H. "Biocatalyst-Initiated ortho-Quinone Methide Formation and Derivatization" J. Am. Chem. Soc. 2019, 141, DOI: 10.1021/jacs.9b10474. (First disclosed on ChemRvix. DOI: 10.26434/chemrxiv.7828769.v1)

33. Baker Dockrey, S. A.; Narayan, A. R. H. "Oxidative Dearomatization by Flavin-Dependent Monooxygenase." Trends in Chemistry 2019. DOI: 10.1016/j.trechm.2019.11.004.

 

32. Benítez Rodríguez, A.; Narayan, A. R. H. "Frontiers in Biocatalysis: Profiling Function across Sequence Space."ACS Cent. Sci. 2019, 5, 1747-1749. DOI: 10.1021/acscentsci.9b01112.

 

31. Pyser, J. B.; Baker Dockrey, S. A.; Benítez Rodríguez, A.; Joyce, L. A.; Wiscons, R. A.; Smith, J. L.; Narayan, A. R. H. "Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products." J. Am. Chem. Soc. 2019, 141, 18551-18559. DOI: 10.1021/jacs.9b9385.

30. Tweedy, S. E.; Rodríguez Benítez, A.; Narayan, A. R. H.; Zimmerman, P. M.; Brooks, C. L., III and Wymore, T. "The hydroxyl radical coupled electron transfer mechanism of flavin-dependent hydroxylases." J. Phys. Chem. B  2019, 123, 38, 8065-8073. DOI: 10.1021/acs.jpcb.9b08178.

29. Baker Dockrey, S. A.; Suh, C.; Rodríguez Benítez, A.; Wymore, T.; Brooks III, C. L.; Narayan, A. R. H. “Positioning group-enabled biocatalytic oxidative dearomatization” ACS Cent. Sci. 2019, 5, 1010-1016. DOI:10.1021/acscentsci9b00163.

28. Doyon, T. J.; Narayan, A. R. H. "Synthetic Utility of One-Pot Chemoenzymatic Reaction Sequences" Synlett 2019 (cluster on biocatalysis). DOI: 10.1055/s-0037-1611848.

27. Lukowski, A. L.; Denomme, N.; Hinze, M. E.; Hall, S.; Isom, L. L.; Narayan, A. R. H. "Biocatalytic Detoxification of Paralytic Shellfish Toxins" ACS Chem. Biol. 2019, 14, 941-948. DOI: 10.1021/acschembio.9b00123.

26. Aspuru-Guzik....Narayan, A. R. H....and many more. "Charting a course for chemistry" Nat. Chem. 2019, 11, 286-294. DOI: 10.1038/s41557-019-0236-7 (Editorial).

25. Chun, S. W.; Narayan, A. R. H. "Biocatalytic Synthesis of α-Amino Ketones" Synlett 2019, 30, 1269-1274. DOI: 10.1055/s-0037-1611755.

24. Narayan, A. R. H. “Enzymes trapped and zapped for use outside cells” Nature 2019, 567, 317-318. DOI: 10.1038/d41586-019-00761-2 (News & Views).

23. Baker Dockrey, S. A. and Narayan, A. R. H. “Flavin-dependent biocatalysts in synthesis” Tetrahedron 2019, 75, 1115-1121. DOI: 10.1016/j.tet.2019.01.008 (Special Issue on Biocatalysis in Organic Synthesis).

22. Lukowski, A. L. and Narayan, A. R. H. “Natural voltage-gated sodium channel ligands: Biosynthesis and biology” ChemBioChem 2019, 20, 1231-1241. DOI: 10.1002/cbic.201800754 (Special Issue: New Talent).

21. Rodríguez Benítez, A.; Tweedy, S. E.; Baker Dockrey, S. A.; Lukowski, A. L.; Wymore, T.; Khare, D.; Brooks, C. L., III; Palfey, B. A.; Smith, J. L.; Narayan A. R. H. "Structural Basis for Selectivity in Flavin-Dependent Monooxygenase-Catalyzed Oxidative Dearomatization." ACS Catal. 2019, 9, 3633-3640. DOI: 10.1021/acscatal.8b04575.

Read our preprint. DOI:10.26434/chemrxiv.7297766.v1

20. Baker Dockrey, S. A.; Doyon, T. J.; Perkins, J. C.; Narayan, A. R. H. “Whole-cell biocatalysis platform for gram-scale oxidative dearomatization of phenols” Chem. Biol. Drug Des. 2019, 93, 1207-1213. DOI:10.1111/cbdd.13443.

19. Lukowski, A. L.; Ellinwood, D. C.; Hinze, M. E.; DeLuca, R. J.; Du Bois, J.; Hall, S.; Narayan, A. R. H. "C−H Hydroxylation in Paralytic Shellfish Toxin Biosynthesis" J. Am. Chem. Soc. 2018, 140, 11863-11869. DOI: 10.1021/jacs.8b08901.

18. Chun, S. W.; Hinze, M. E.; Skiba, M. A.; Narayan, A. R. H. "Chemistry of a unique polyketide-like synthase" J. Am. Chem. Soc. 2018, 140, 2430-2433. DOI: 10.1021/jacs.7b13297.

17. Baker Dockrey, S. A.; Lukowski, A. L.; Becker, M. R.; Narayan, A. R. H.  “Biocatalytic site- and enantioselective oxidative dearomatization of phenols” Nature Chem. 2018, 10, 119-125. DOI: 10.1038/nchem.2879.

Mentored Publications

16. Gilbert, M. M.; DeMars, M. D.; Yang, S.; Grandner, J. M.; Wang, S.; Wang, H.; Narayan, A. R. H.; Sherman, D. H.; Houk, K. N.; Montgomery, J. "Synthesis of Diverse 11- and 12-Membered Macrolactones from a Common Linear Substrate Using a Single Biocatalyst” ACS Cent. Sci. 2017, 3, 1304-1310. DOI: 10.1021/acscentsci.7b00450.

15. Narayan, A. R. H.; Jiménez-Osés, G.; Liu, P.; Negretti, S.; Zhao, W.; Ramabhadr, R. O.; Furan, L.; Li, Z.; Yang, Y.-F.; Gilbert, M.; Podust, L. M.; Montgomery, J.; Houk, K. N.; Sherman, D. H.  “Enzymatic Hydroxylation of an Unactivated Methylene C–H Bond Guided by Molecular Dynamics Simulations” Nature Chem. 2015, 7, 653-660.

14. Dutta, S.; Whicher, J. R.; Hansen, D. A.; Hale, W. A.; Chemler, J. A.; Narayan, A. R. N.; Hakansson, K.; Sherman, D. H.; Smith, J. L.; Skiniotis, G. “Structure of a modular polyketide synthase” Nature 2014, 510, 512-517.

13. Whicher, J. R.; Dutta, S.; Hansen, D. A.; Hale, W. A.; Chemler, J. A.; Narayan, A. R. N.; Hakansson, K.; Sherman, D. H.; Smith, J. L.; Skiniotis, G. “Structural rearrangements of a PKS module during its catalytic cycle” Nature 2014, 510, 560-564.

12. Negretti, S.*; Narayan, A. R. H.*; Chiou, K. C.; Kells, P. M.; Stachowski, J. L.; Hansen, D. A.; Podust, L. M.; Montgomery, J.; Sherman, D. H. “Directing group-controlled regioselectivity in an enzymatic C-H bond oxygenation” J. Am. Chem. Soc. 2014, 136, 4901-4904. *Denotes equal contribution

11. Heller, S. T.; Kiho, T.; Narayan, A. R. H.; Sarpong, R. “Protic Solvent Mediated Cycloisomerization of Quinoline and Isoquinoline Propargylic Carbinols: Syntheses of (±)-3-Demethoxyerythratidinone and (±)-Cocculidine” Angew. Chem. Int. Ed. 2013, 52, 11129-11133.

10. Hansen, D. H.; Rath, C. M.; Eisman, E. B.; Narayan, A. R. H.; Kittendorf, J. D.; Mortison, J. D.; Yoon, Y. J.; Sherman, D. H. “Biocatalytic Synthesis of Pikromycin, Methymycin, Neomethymycin, Novamethymycin, and Ketomethymycin” J. Am. Chem. Soc.2013, 135, 11232-11238.

9. Narayan, A. R. H.; Sherman, D. H. “Re-engineering nature’s catalysts” Science 2013, 339, 283-284.

8. Hardin Narayan, A. R.; Sarpong, R. "Indolizinones as Synthetic Scaffolds: Fundamental Reactivity and the Relay of Stereochemical Information" Org. Biomol. Chem. 2012, 10, 70-78.

7. Hardin Narayan, A. R.; Sarpong, R. “Remarkable Facilitation of Hetero-Cycloisomerizations with Water and Other Polar Protic Solvents: Metal-Free Synthesis of Indolizines” Green Chem. 2010, 10, 1556-1559.

6. Hardin Narayan, A. R.; Simmons, E. R.; Sarpong, R. “Synthetic strategies toward the cortistatin family of natural products” Eur. J. Org. Chem. 2010, 3553-3567.

5. Simmons, E. M.; Hardin, A. R.; Guo, X.; Sarpong, R. "Formal total synthesis of (±)-cortistatin A" Tetrahedron 2010, 66, 4696-4700.

4. Simmons, E. M.; Hardin, A. R.; Guo, X.; Sarpong, R. “Rapid Construction of the Cortistatin Pentacyclic Core” Angew. Chem. Int. Ed. 2008, 47, 6650 – 6653.

3. Hardin, A. R.; Sarpong, R. "Electronic Effects in the Pt-Catalyzed Cycloisomerization of Propargylic Esters: Synthesis of 2,3-Disubstituted Indolizines as a Mechanistic Probe" Org. Lett. 2007, 9, 4547-4550.

2. Adams, J.; Hardin, A. R.; Vounatsos, F. “Microwave-Assisted Synthesis of New Polysubstituted Dienaminoesters and Their Cyclization to 3-Bromo-2(1H)-Pyridinones” J. Org. Chem. 2006, 71, 9895-9898.

1. Hay, M.; Hardin, A. R.; Wolfe, J. P. “Palladium-Catalyzed Synthesis of Tetrahydrofurans from γ-Hydroxy Terminal Alkenes:  Scope, Limitations, and Stereoselectivity” J. Org. Chem. 2005, 70, 3099-3107.