The Fasan Lab | Publications

Publications

86. Enantioselective single and dual a-C–H bond Functionalization of Cyclic Amines via Enzymatic Carbene Transfer

Ren X, Couture BM, Liu N, Lall MS, Kohrt JT, and Fasan* R

J. Am. Chem. Soc. 2022; accepted PDF.

85. Dehaloperoxidase Catalyzed Stereoselective Synthesis of Cyclopropanol Esters

Siriboe MG, Vargas DA, and Fasan* R

Journal of Organic Chemistry 2022; accepted PDF.

84. Engineered Myoglobin Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions

Siriboe MG, and Fasan* R

Bull. Chem. Soc. Jpn. 2022; 80 4-13 PDF.

→ Award Review Article

83. Highly stereoselective and enantiodivergent synthesis of cyclopropylphosphonates with engineered carbene transferases

Ren X, Chandgude AL, Carminati DM, Shen Z, Khare SD and Fasan* R

Chemical Science 2022; 61, 11, 1041–1054 PDF.

82. Tuning Enzyme Thermostability via Computationally Guided Covalent Stapling and Structural Basis of Enhanced Stabilization

Iannuzzelli JA, Bacik JP, Moore EJ, Shen Z, Irving EM, Vargas DA, Khare* SD, Ando* N, and Fasan* R

Biochemistry 2022; 61, 11, 1041–1054 PDF.

81. Enantioselective Synthesis of alpha-Trifluoromethyl Amines via Biocatalytic N–H Bond Insertion with Acceptor-Acceptor Carbene Donors

Nam D, Tinoco A, Shen Z, Adukure RD, Sreenilayam D, Khare* SD, and Fasan* R

J. Am. Chem. Soc. 2022; 144 (6) 2590–2602 PDF.

80. Nanoparticle-Mediated Delivery of Micheliolide Analogs to Eliminate Leukemic Stem Cells in the Bone Marrow

Ackun-Farmmer MA, Hanan Alwaseem H, Counts M, Bortz A, Giovani S, Frisch* BJ, Fasan* R, and Benoit DSW

Advanced Therapeutics 2022; 5 (1) 2100100 PDF.

79. Engineered and artificial metalloenzymes for selective C–H functionalization

Ren X, and Fasan* R

Current Opinion in Green and Sustainable Chemistry 2021; 31 PDF.

78. Cyclic peptides with a distinct arginine-fork motif recognize the HIV trans-activation response RNA in vitro and in cells

Chavali^† SS, Mali^† SM, Jenkins JL, Bonn RMS, Saseendran Anitha A, Bennett, RP, Smith, HC, Fasan* R, and Wedekind* JE

J. Biol. Chem. 2021; 297, 6 PDF.

^† equal contribution

77. Comprehensive Structure–Activity Profiling of Micheliolide and its Targeted Proteome in Leukemia Cells via Probe-Guided Late-Stage C–H Functionalization

Alwaseem H, Giovani S, Crotti M, Welle K, Jordan G T, Ghaemmaghami S, and Fasan* R

ACS Cent. Sci. 2021; 7 (5) 841–857 PDF.

76. A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones

Nam D, Steck V, Potenzino RJ, and Fasan* R

J. Am. Chem. Soc. 2021; 143(5) 2221–2231 PDF.

75. Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2‐Containing Trisubstituted Cyclopropanes

Carminati DM, Decaens J, Couve‐Bonnaire S, Jubault P, and Fasan* R

Angew. Chem. Int. Ed. 2021; 60 1-6 PDF.

→ Highlighted as “Hot Paper”

→Highlighted in Synfacts.

74. Co-crystal structures of HIV TAR RNA bound to lab-evolved proteins show key roles for arginine relevant to the design of cyclic peptide TAR inhibitors

Chavali SS, Mali SM, Jenkins JL, Fasan R,and Wedekind* JE

J. Biol. Chem. 2020; 295(49) 16470-16486 PDF.

→ Selected as “Editor’s pick” article and for Journal Cover

73. An enzymatic platform for the highly enantioselective and stereodivergent construction of cyclopropyl-delta-lactones

Ren^†X, Liu^†N, Chandgude AL, and Fasan* R

Angew. Chem. Int. Ed. 2020; 59 2-8 PDF.
^† equal contribution

→Highlighted in Synfacts.

→Highlighted in Organic Chemistry Portal.

72. Enantioselective Synthesis of Chiral Amines via Biocatalytic Carbene N-H Insertion

Steck V, Carminati DM, Johnson NR, and Fasan* R

ACS Catal. 2020; 10 10967−10977 PDF.

71. Strategies for the Expression and Characterization of Artificial Myoglobin-based Carbene Transferases

Carminati DM, Moore EJ, and Fasan* R

Methods in Enzymology 2020; 644 35-61 PDF.

70. Organic Solvent Stability and Long-term Storage of Myoglobin-based Carbene Transfer Biocatalysts

Pineda-Knauseder^† AJ, Vargas^† DA, and Fasan* R

Biotechnology and Applied Biochemistry 2020; 67 (4) 516- 526 PDF.
^† equal contribution

69. Expanded toolbox for directing the biosynthesis of macrocyclic peptides in bacterial cells

Iannuzzelli JA, and Fasan* R

Chemical Science 2020; 11, 6202-6208 PDF.

68. Synergistic catalysis in an artificial enzyme

Ren X, and Fasan* R

Nature Chemistry 2020; 3, 184-185 PDF.

67. C-H Amination via Nitrene Transfer Catalyzed by Mononuclear Non‐Heme Iron‐Dependent Enzymes

Vila^† MA, Steck^† V, Giordano SR, Carrera* I, and Fasan* R

ChemBioChem 2020; 21 (14), 1981- 1987 PDF.
^† equal contribution

→Highlighted in ChemistryViews Magazine

66. Mechanism-Guided Design and Discovery of Efficient Cytochrome P450 Derived C-H Amination Biocatalysts

Steck^† V, Kolev^† JN, Ren X, and Fasan* R

J. Am. Chem. Soc. 2020; 142 (23), 10343–10357 PDF.
^† equal contribution

65. Blocking SHH/Patched interaction triggers tumor growth inhibition through Patched-induced apoptosis

Bissey AP, Mathot P, Guix C, Jasmin M, Goddard I, Costechareyre C, Gadot N, Delcros JG, Mali SM, Fasan R, Arrigo AP, Dante R, Ichim G, Mehlen P, Fombonne J

Cancer Research 2020; 80 (10) 1970-1980 PDF.

64. MOrPH-PhD: an integrated phage display platform for the discovery of functional genetically-encoded peptide macrocycles

Owens AE, Iannuzzelli JA, Gu Y, and Fasan* R

ACS Cent. Sci. 2020; 6 (3), 368–381 PDF.

63. Highly Stereoselective Synthesis of Fused Cyclopropane-γ-Lactams via Biocatalytic Iron-Catalyzed Intramolecular Cyclopropanation

Ren^† X, Chandgude^† AL, and Fasan* R

ACS Catal. 2020; 10(3) 2308-2313 PDF.
^† equal contribution

62. Structure of sonic hedgehog protein in complex with Zn(II) and Mg(II) reveals ion coordination plasticity relevant to peptide drug design

Bonn-Breach R, Gu Y, Jenkins J, Fasan R, Wedekind W*

Acta Crystallographica D 2019; D75 969-979 PDF.

61. A continuing career in biocatalysis: Frances H. Arnold

Fasan* R, Kan* SBJ, Zhao* H

ACS Catal. 2019; 9 9683-9697 (Invited article in honour of 2018 Nobel Laureate Frances Arnold)

60. Stereoselective Cyclopropanation of Electron-Deficient Olefins with a Cofactor Redesigned Carbene Transferase Featuring Radical Reactivity

Carminati D, and Fasan* R

ACS Catal. 2019; 9 9683-9697 PDF.

59. Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N–H Insertion

Steck V, Sreenilayam G, and Fasan* R

Synlett 2019; 30 A-F PDF.

58. Mechanistic Investigation of Biocatalytic Heme Carbenoid Si−H Insertions

Khade R, Chandgude A, Fasan* R and Zhang* Y

ChemCatChem 2019; 11,13 3101-3108 PDF.

57. Biocatalytic Strategy for Highly Diastereo‐ and Enantioselective Synthesis of 2,3‐Dihydrobenzofuran‐Based Tricyclic Scaffolds

Vargas D, Khade R, Zhang* Y and Fasan* R

Angew. Chem. Int. Ed. 2019; 58,30 10148-10152 PDF.

56. Stereodivergent Intramolecular Cyclopropanation Enabled by Engineered Carbene Transferases

Chandgude AL, Ren X, and Fasan* R

J. Am. Chem. Soc. 2019; 141, 23 9145-9150 PDF.

→ Highlighted in Nature Catalysis

→ Highlighted in SYNFACTS

55. Effect of proximal ligand substitutions on the carbene and nitrene transferase activity of myoglobin

Moore E , and Fasan* R

Tetrahedron 2019; 75, 16 2357-2363 PDF.

54. Origin of High Stereocontrol in Olefin Cyclopropanation Catalyzed by an Engineered Carbene Transferase

Tinoco A, Wei Y, Bacik JP, Carminati D, Moore E , Ando N, Zhang Y , and Fasan* R

ACS Catal. 2019; 9 1514-1524 PDF.

53. Highly Diastereo- and Enantioselective Synthesis of Nitrile-Substituted Cyclopropanes by Myoglobin-Mediated Carbene Transfer Catalysis

Chandgude AL, and Fasan* R

Angew. Chem. Int. Ed. 2018; 57, 48 15852-15856 PDF.

52. Myoglobin-catalyzed C—H functionalization of unprotected indoles

Vargas D, Tinoco A , Tyagi V and Fasan* R

Angew. Chem. Int. Ed. 2018; 57 9911–9915 PDF.

51. Chemoselective Cyclopropanation over Carbene Y—H insertion Catalyzed by an Engineered Carbene Transferase

Moore E, Steck V, Bajaj P and Fasan* R

J. Org. Chem. 2018; 83, 14 7480-7490 PDF.

50. Cyclopropanations via Heme Carbenes: Basic Mechanism and Effects of Carbene Substituent, Protein Axial Ligand, and Porphyrin Substitution

Wei Y, Tinoco A , Steck V, Fasan* R , and Zhang* Y

J. Am. Chem. Soc. 2018; 140 (5) 1649–1662 PDF.

49. Transcriptional coactivator PGC-1α contains a novel CBP80-binding motif that orchestrates efficient target gene expression

Cho H, Rambout X, Gleghorn ML, Nguyen PQT, Phipps CR, Miyoshi K, Myers JR, Kataoka N, Fasan R and Maquat* LE

Gene Dev. 2018; in press PDF.

48. Stabilization of the Reductase Domain in the Catalytically Self-Sufficient Cytochrome P450BM3 via Consensus-Guided Mutagenesis

Saab-Rincón* G, Alwaseem H, Guzmán-Luna V, Olvera L and Fasan R

ChemBioChem 2018; 19(6) 622-632 PDF.

47. Enzyme stabilization via computationally guided protein stapling

Moore EJ, Zorine D, Hansen WA, Khare* SD, Fasan* R

Proc. Nat. Acad. Sci. USA 2017; 114 (47) 12472–12477 PDF.

46. Stereoselective olefin cyclopropanation under aerobic conditions with an artificial enzyme incorporating an iron-chlorin e6 cofactor

Sreenilayam G, Moore EJ, Steck V, Fasan* R

ACS Catal. 2017; 7 7629−7633 PDF.

45. Anticancer activity profiling of parthenolide analogs generated via P450-mediated chemoenzymatic synthesis

Alwaseem H, Frisch BJ, Fasan* R

Bioorg. Med. Chem. 2018; 26 1365–1373 PDF.

44. Design and Evolution of a Macrocyclic Peptide Inhibitor of the Sonic Hedgehog/Patched Protein-Protein Interaction

Owens AE, de Paola I, Hansen WA, Liu YW, Khare SD, Fasan* R

J. Am. Chem. Soc. 2017; 139 (36) 12559-12568 PDF.

→ Selected as JACS Spotlight paper

→ Highlighted in Chemical & Engineering News

→ Highlighted in University of Rochester Newscenter

43. Exploiting and engineering hemoproteins for abiological carbene and nitrene transfer reactions

Brandenberg OF, Fasan* R and Arnold* FH

Curr. Opin. Biotechnol. 2017; 47 102–111 PDF.

42. New functional twists for P450s

Fasan R

Nat. Chem. 2017; 9 (7) 609-611 PDF.

41. Metal substitution modulates the reactivity and extends the reaction scope of myoglobin carbene transfer catalysts

Sreenilayam G, Moore EJ, Steck V, and Fasan* R

Adv. Synth. Cat. 2017; 359 (12) 2076–2089 PDF.

40. Highly Diastereo- and Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes via Myoglobin-Catalyzed Transfer of Trifluoromethylcarbene

Tinoco A, Steck V, Tyagi V and Fasan* R

J. Am. Chem. Soc. 2017; 139 (15) 5293–5296 PDF.

→ Highlighted in Chemical & Engineering News

→ Highlighted in SYNFACTS

39. Two-tier Screening Platform for Directed Evolution of AminoacyltRNA Synthetases with Enhanced Stop Codon Suppression Efficiency

Owens AE, Grasso K, Ziegler C and Fasan* R

ChemBioChem 2017; 18 (12) 1109–1116 PDF.

38. Ribosomal Synthesis of Thioether-Bridged Bicyclic Peptides

Bionda N and Fasan* R

Methods Mol. Biol. 2016; 1495 57-76 PDF.

37. Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity

Bajaj P, Sreenilayam G, Tyagi V and Fasan* R

Angew. Chem. Int. Ed. 2016; 55 16110–16114, PDF.

→ Highlighted in SYNFACTS

→ Highlighted in ACIE

36. Biocatalytic Synthesis of Allylic and Allenyl Sulfides through a Myoglobin-Catalyzed Doyle–Kirmse Reaction

Tyagi V, Sreenilayam G, Bajaj P, Tinoco A and Fasan* R

Angew. Chem. Int. Ed. 2016; 55 13562 –13566, PDF.

35. Chemoenzymatic synthesis and antileukemic activity of novel C9- and C14-functionalized parthenolide analogs

Tyagi V, Alwaseem H, O’Dwyer KM, Ponder J, Li QY, Jordan CT, and Fasan* R

Bioorg. Med. Chem. 2016; 24 3876–3886, PDF

34. Aldehyde and ketone synthesis via P450-catalyzed oxidative deamination of alkyl azides

Giovani S, Alwaseem H, and Fasan* R

ChemCatChem 2016; 8 2609–2613 , PDF.

33. Side-chain-to-tail cyclization of ribosomally derived peptides promoted by aryl and alkyl amino-functionalized unnatural amino acids

Frost JR, Wu Z, Lam YC, Owens AE, and Fasan* R

Org. Biomol. Chem. 2016; 14 5803-5812, PDF

32. Myoglobin-catalyzed olefination of aldehydes

Tyagi V, and Fasan* R

Angew. Chem. Int. Ed. 2016; 55 2512–2516, PDF.

→ Highlighted in SYNFORM

→ Highlighted in SYNFACTS

31. Efficient conversion of primary azides to aldehydes catalyzed by active site variants of myoglobin

Giovani S, Singh R, and Fasan* R

Chem. Sci. 2016; 7 234-239, PDF

30. Ribosomal synthesis of natural product-like bicyclic peptides in E. coli

Bionda N, and Fasan* R

ChemBioChem 2015; 16 2011-2016, PDF

29. Ribosomal Synthesis of Macrocyclic Peptides in Vitro and in Vivo Mediated by Genetically Encoded Amino-Thiol Unnatural Amino Acids

Frost JR, Jacob NT, Papa L, Owens A, and Fasan* R

ACS Chem. Biol. 2015; 10 (8), 1805–1816, PDF.

28. Intermolecular carbene S-H insertion catalyzed by engineered myoglobin-based catalysts

Tyagi V, Bonn RB, and Fasan* R

Chem. Sci. 2015; 6, 2488-2494, PDF.

→ Highlighted in Nature Chemistry

27. Synthesis of Macrocyclic Organo-Peptide Hybrids from Ribosomal Polypeptide Precursors via CuAAC-/hydrazide-mediated cyclization

Smith JM, and Fasan* R

Meth. Mol. Biol. 2015; 1248, 23-38

26. Myoglobin-catalyzed intermolecular carbene N-H insertion with arylamine substrates

Sreenilayam G, and Fasan* R

Chem. Commun. 2015; 15 1532-1534.

25. Highly Diastereoselective and Enantioselective Olefin Cyclopropanation Using Engineered Myoglobin-Based Catalysts

Bordeaux M, Tyagi V, and Fasan* R

Angew. Chem. Int. Ed. 2015; 54 (6), 1744-1748, PDF.

24. Enzymatic C(sp3)—H amination: P450-catalyzed conversion of carbonazidates into oxazolidinones

Singh R, Kolev JN, Sutera PA, and Fasan* R

ACS Catal. 2015; 5 (3), 1685-1691, PDF.

→ Selected for the inside back cover of the February issue

→ Highlighted in SYNFACTS

23. Bioinspired strategy for the ribosomal synthesis of thioether-bridged macrocyclic peptides in bacteria

Bionda N, Cryan AL, and Fasan* R

ACS Chem. Biol. 2014; 9 (9) 2008 - 2013, PDF.

22. Intramolecular C(sp3)—H amination of arylsulfonyl azides with engineered and artificial myoglobin-based catalysts

Bordeaux M, Singh R, and Fasan* R

Bioorganic Med. Chem. 2014; 22 (20) 5697 – 5704, PDF.

→ Contribution to special issue "Natural, engineered, and artificial biocatalysts for organic synthesis" (Guest Editor: Rudi Fasan) in occasion of 2014 Tetrahedron Young Investigator Award

21. Designer macrocyclic organo-peptide hybrids inhibit the interaction between p53 and HDM2/X by accommodating a functional α-helix

Smith JM, Frost JR, and Fasan* R

Chem. Commun. 2014; 50 (39) 5027 - 5030, PDF.

20. Enhancing the Efficiency and Regioselectivity of P450 Oxidation Catalysts via Unnatural Amino Acid Mutagenesis

Kolev NJ, Zaengle JM,Ravikumar R, and Fasan* R

ChemBioChem 2014; 15 (7) 1001-1010, PDF.

19. P450-catalyzed intramolecular sp3 C—H amination with arylsulfonyl azide substrates

Singh R, Bordeaux M, and Fasan* R

ACS Catal. 2014; 4 (2) 546–552, PDF.

→ Highlighted in SYNFACTS

→ Highlighted in Angewandte Chemie International Edition

18. Synthesis of bicyclic organo-peptide hybrids via oxime/intein-mediated macrocyclization followed by disulfide bond formation

Smith JM, Hill NC, Krasniak PJ, and Fasan* R

Org. Biomol. Chemistry 2014; 12 (7), 1135-1142, PDF.

17. Discovery of potent parthenolide-based antileukemic agents enabled by late-stage P450-mediated C―H functionalization

Kolev NJ, O'Dwyer KM, Jordan CT, and Fasan* R

ACS Chem. Biol. 2014; 9 (1), 164-173, PDF

→ Highlighted in Chemical Research in Toxicol

16. Design, synthesis, and diversification of ribosomally derived peptide macrocycles

Frost JR, Smith JM, and Fasan* R

Curr. Opin. Struct. Biol. 2013; 23(4), 571-580.

15. Emerging Strategies to Access Peptide Macrocycles from Genetically Encoded Polypeptides

Smith JM, Frost JR, and Fasan* R

J. Org. Chem. 2013; 78(8), 3525–3531, PDF.

14. Macrocyclization of Organo-Peptide Hybrids via a Dual Bioorthogonal Ligation: Insights from Structure-Reactivity Studies

Frost JR, Vitali F, Jacob NT, Brown MD, and Fasan* R

ChemBioChem 2013; 14(1), 147-160, PDF.

13. Controlled Oxidation of Remote sp3 C-H Bonds in Artemisinin via P450 Catalysts with Fine-Tuned Regio- and Stereoselectivity

Zhang K, Shafer BM, Demars II MD, Stern HA, and Fasan* R

J. Am. Chem. Soc. 2012; 134(45), 18695–18704, PDF.

→ Highlighted in Chemical & Engineering News

→ Highlighted in JACS Spotlight

→ Highlighted in Faculty1000

12. Tuning P450 Enzymes as Oxidation Catalysts

Fasan* R
ACS Catal. 2012; 2, 647-666, PDF.

→ Selected for the cover of the April issue

11. Diverse Organo-Peptide Macrocycles via a Fast and Catalyst-Free Oxime/Intein-Mediated Dual Ligation

Satyanarayana M, Vitali F, Frost JR, and Fasan* R
Chem. Commun. 2012; 48(10), 1461-1463, PDF.

10. Modular Assembly of Macrocyclic Organo-Peptide Hybrids using Synthetic and Genetically Encoded Precursors

Smith JM, Vitali F, Archer SA, and Fasan* R
Angew. Chem. Int. Ed. Engl. 2011; 50(22), 5075-5080, PDF.

→ Selected as 'Hot Paper' by the journal editorial board.

9. P450 Fingerprinting Method for Rapid Discovery of Terpene Hydroxylating P450 Catalysts with Diversified Regioselectivity

Zhang Z, El Damaty S, and Fasan* R
J. Am. Chem. Soc. 2011; 133(10), 3242-3245, PDF.

From Postdoctoral and Graduate Studies

8."Chemo-Enzymatic Fluorination of Unactivated Organic Compounds", Rentmeister A, Arnold FH, Fasan* R Nat. Chem. Biol. 2009; 5(1), 26-28, PDF.

→ Highlighted by Faculty of 1000 ("Must Read").

→ Highlighted by Graham Sandford in "Engineering fluorination" Nat. Chem. Biol. 5, 6-7.

→ Highlighted by Cormac Murphy in "Fluorinated drug metabolism in microorganisms" Chimica Oggi-Chemistry Today 30, 16-19.

7. "Improved product-per-glucose yields in P450-dependent biotransformations using engineered E. coli", Fasan R, Crook NC, Peters MW, Meinhold P, Buelter T, Landwehr M, Cirino PC, Arnold* FH Biotechnol. Bioeng. 2011; 108(3), 500-510, PDF.

6. "Evolutionary history of a specialized propane monooxygenase", Fasan R, Meharenna YT, Snow CD, Poulos TL, Arnold* FH J. Mol. Biol. 2008; 383(5), 1069-1080, PDF.

5. "Engineered alkane-hydroxylating cytochrome P450BM3 exhibiting native-like catalytic properties", Fasan R, Chen MM, Crook NC, Arnold* FH Angew. Chem. Int. Ed. Engl. 2007; 46(44), 8414-8418, PDF.

4. "Structure-activity studies in a family of beta-hairpin protein epitope mimetic inhibitors of the p53-HDM2 protein-protein interaction", Fasan R, Dias RL, Moehle K, Zerbe O, Obrecht D, Mittl PR, Grütter MG, Robinson* JA ChemBioChem 2006; 7(3), 515-526, PDF.

3. "Protein ligand design: from phage display to synthetic protein epitope mimetics in human antibody Fc-binding peptidomimetics", Dias RL, Fasan R, Moehle K, Renard A, Obrecht D, Robinson* JA J. Am. Chem. Soc. 2006; 128(8), 2726-2732, PDF.

2. "Molecular basis of RNA recognition by the human alternative splicing factor Fox-1", Auweter SD, Fasan R, Reymond L, Underwood JG, Black DL, Pitsch S, Allain* FH EMBO J. 2006; 25(1), 163-173, PDF.

1. "Using a beta-hairpin to mimic an alpha-helix: cyclic peptidomimetic inhibitors of the p53-HDM2 protein-protein interaction", Fasan R, Dias RL, Moehle K, Zerbe O, Vrijbloed JW, Robinson* JA Angewandte Chemie International Edition in English 2004; 43(16), 2109-2112, PDF.

→ Highlighted by Faculty of 1000.