Genetically programmed chiral organoborane synthesis

Nature

Volumn 552, Issue 7683, 2017, Pages 132-136

  Jennifer Kan, S B ^a   Huang, Xiongyi ^a   Gumulya, Yosephine ^a   Chen, Kai ^a   Arnold, Frances H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CARBENE; CYTOCHROME C; LEWIS BASE; ORGANOBORON DERIVATIVE; BORON; HYDROGEN;

BACTERIUM; BIOTRANSFORMATION; CATALYSIS; CATALYST; CELL; ENZYME ACTIVITY; GENETIC ENGINEERING;

ARTICLE; BIOCATALYSIS; BORYLATION; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ENGINEERING; ESCHERICHIA COLI; HYDROGEN BOND; NONHUMAN; PRIORITY JOURNAL; RHODOTHERMUS; RHODOTHERMUS MARINUS; CHEMICAL STRUCTURE; CHEMISTRY; DIRECTED MOLECULAR EVOLUTION; ENZYMOLOGY; GENETICS; METABOLIC ENGINEERING; METABOLISM; STEREOISOMERISM;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; RHODOTHERMUS;

BIOCATALYSIS; BORON; CYTOCHROMES C; DIRECTED MOLECULAR EVOLUTION; ESCHERICHIA COLI; HYDROGEN; HYDROGEN BONDING; METABOLIC ENGINEERING; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR STRUCTURE; RHODOTHERMUS; STEREOISOMERISM;

EID: 85040338163     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature24996     Document Type: Article

References (44)

1. Renata, H., Wang, Z. J. & Arnold, F. H. Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution. Angew. Chem. Int. Ed. 54, 3351-3367 (2015).
2. Hyster, T. K. & Ward, T. R. Genetic optimization of metalloenzymes: enhancing enzymes for non-natural reactions. Angew. Chem. Int. Ed. 55, 7344-7357 (2016).
3. Hammer, S. C., Knight, A. M. & Arnold, F. H. Design and evolution of enzymes for non-natural chemistry. Curr. Opin. Green Sustainable Chem. 7, 23-30 (2017)
4. Coelho, P. S. et al. A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo. Nat. Chem. Biol. 9, 485-487 (2013).
5. Jeschek, M. et al. Directed evolution of artificial metalloenzymes for in vivo metathesis. Nature 537, 661-665 (2016).
6. Kan, S. B. J., Lewis, R. D., Chen, K. & Arnold, F. H. Directed evolution of cytochrome c for carbon-silicon bond formation: Bringing silicon to life. Science 354, 1048-1051 (2016).
7. Tinoco, A., Steck, V., Tyagi, V. & Fasan, R. Highly diastereo- and enantioselective synthesis of trifluoromethyl-substituted cyclopropanes via myoglobin-catalyzed transfer of trifluoromethylcarbene. J. Am. Chem. Soc. 139, 5293-5296 (2017).
8. Stelter, M. et al. A novel type of monoheme cytochrome c: biochemical and structural characterization at 1.23 A resolution of Rhodothermus marinus cytochrome c. Biochemistry 47, 11953-11963 (2008).
9. Cheng, Q.-Q., Zhu, S.-F., Zhang, Y.-Z., Xie, X.-L. & Zhou, Q.-L. Copper-catalyzed B-H bond insertion reaction: a highly efficient and enantioselective C-B bond-forming reaction with amine-borane and phosphine-borane adducts. J. Am. Chem. Soc. 135, 14094-14097 (2013).
10. Chen, D., Zhang, X., Qi, W.-Y., Xu, B. & Xu, M.-H. Rhodium(i)-catalyzed asymmetric carbene insertion into B-H bonds: highly enantioselective access to functionalized organoboranes. J. Am. Chem. Soc. 137, 5268-5271 (2015).
11. Hyde, S. et al. Copper-catalyzed insertion into heteroatom-hydrogen bonds with trifluorodiazoalkanes. Angew. Chem. Int. Ed. 55, 3785-3789 (2016).
12. Irschik, H., Schummer, D., Gerth, K., Höfle, G. & Reichenbach, H. The tartrolons, new boron-containing antibiotics from a myxobacterium, Sorangium cellulosum. J. Antibiot. 48, 26-30 (1995).
13. Wolkenstein, K., Sun, H., Falk, H. & Griesinger, C. Structure and absolute configuration of Jurassic polyketide-derived spiroborate pigments obtained from microgram quantities. J. Am. Chem. Soc. 137, 13460-13463 (2015).
14. Chen, X. et al. Structural identification of a bacterial quorum-sensing signal containing boron. Nature 415, 545-549 (2002).
15. Elshahawi, S. I. et al. Boronated tartrolon antibiotic produced by symbiotic cellulose-degrading bacteria in shipworm gills. Proc. Natl Acad. Sci. USA 110, E295-E304 (2013).
16. Dembitsky, V. M., Al Quntar, A. A. & Srebnik, M. Natural and synthetic small boron-containing molecules as potential inhibitors of bacterial and fungal quorum sensing. Chem. Rev. 111, 209-237 (2011).
17. Prier, C. K., Zhang, R. K., Buller, A. R., Brinkmann-Chen, S. & Arnold, F. H. Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme. Nat. Chem. 9, 629-634 (2017).
18. Das, B. C. et al. Boron chemicals in diagnosis and therapeutics. Future Med. Chem. 5, 653-676 (2013).
19. Miyaura, N. & Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 95, 2457-2483 (1995).
20. Leonori, D. & Aggarwal, V. K. Lithiation-borylation methodology and its application in synthesis. Acc. Chem. Res. 47, 3174-3183 (2014).
21. Leonori, D. & Aggarwal, V. K. Stereospecific couplings of secondary and tertiary boronic esters. Angew. Chem. Int. Ed. 54, 1082-1096 (2015).
22. Tehfe, M. A. et al. A water-compatible NHC-borane: Photopolymerizations in water and rate constants for elementary radical reactions. ACS Macro Lett. 1, 92-95 (2012).
23. Handa, S., Wang, Y., Gallou, F. & Lipshutz, B. H. Sustainable Fe-ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water. Science 349, 1087-1091 (2015).
24. Chang, M. C. Y., Pralle, A., Isacoff, E. Y. & Chang, C. J. A selective, cell-permeable optical probe for hydrogen peroxide in living cells. J. Am. Chem. Soc. 126, 15392-15393 (2004).
25. Halo, T. L., Appelbaum, J., Hobert, E. M., Balkin, D. M. & Schepartz, A. Selective recognition of protein tetraserine motifs with a cell-permeable, pro-fluorescent bis-boronic acid. J. Am. Chem. Soc. 131, 438-439 (2009).
26. Kim, J. & Bertozzi, C. R. A bioorthogonal reaction of N-oxide and boron reagents. Angew. Chem. Int. Ed. 54, 15777-15781 (2015).
27. Li, X. & Curran, D. P. Insertion of reactive rhodium carbenes into boron-hydrogen bonds of stable N-heterocyclic carbene boranes. J. Am. Chem. Soc. 135, 12076-12081 (2013).
28. Curran, D. P. et al. Synthesis and reactions of N-heterocyclic carbene boranes. Angew. Chem. Int. Ed. 50, 10294-10317 (2011).
29. Würtemberger-Pietsch, S., Radius, U. & Marder, T. B. 25 years of N-heterocyclic carbenes: activation of both main-group element-element bonds and NHCs themselves. Dalton Trans. 45, 5880-5895 (2016).
30. Arslan, E., Schulz, H., Zufferey, R., Künzler, P & Thöny-Meyer, L. Overproduction of the Bradyrhizobium japonicum c-type cytochrome subunits of the cbb3 oxidase in Escherichia coli. Biochem. Biophys. Res. Commun. 251, 744-747 (1998).
31. Kille, S. et al. Reducing codon redundancy and screening effort of combinatorial protein libraries created by saturation mutagenesis. ACS Synth. Biol. 2, 83-92 (2013).
32. Mara, M. W. et al. Metalloprotein entatic control of ligand-metal bonds quantified by ultrafast X-ray spectroscopy. Science 356, 1276-1280 (2017).
33. Renata, H. et al. Identification of mechanism-based inactivation in P450-catalyzed cyclopropanation facilitates engineering of improved enzymes. J. Am. Chem. Soc. 138, 12527-12533 (2016).
34. Hernandez, K. E. et al. Highly stereoselective biocatalytic synthesis of key cyclopropane intermediate to ticagrelor. ACS Catal. 6, 7810-7813 (2016).
35. Argintaru, O. A., Ryu, D., Aron, I. & Molander, G. A. Synthesis and applications of α-trifluoromethylated alkylboron compounds. Angew. Chem. Int. Ed. 52, 13656-13660 (2013).
36. 3 and organoboron functional groups. J. Org. Chem. 82, 1951-1960 (2017).
37. Kanouni, T., Stafford, J. A., Veal, J. M. & Wallace, M. B. Histone demethylase inhibitors. WO 2014/151106 A1 (2014).
38. Scopes, D. Pyrrolo [3,2-E] [1,2,4] triazolo [1,5-A] pyrimidines derivatives as inhibitors of microglia activation. US patent 2012/0289523 A1 (2012).
39. Gibson, D. G. et al. Enzymatic assembly of DNA molecules up to several hundred kilobases. Nat. Methods 6, 343-345 (2009).
40. Sambrook, J., Frisch, E. & Maniatis, T. Molecular Cloning: A Laboratory Manual (Cold Spring Harbor Laboratory Press, 1989).
41. Berry, E. A. & Trumpower, B. L. Simultaneous determination of hemes a, b, and c from pyridine hemochrome spectra. Anal. Biochem. 161, 1-15 (1987).
42. Yang, J.-M. et al. Catalytic B−H bond insertion reactions using alkynes as carbene precursors. J. Am. Chem. Soc. 139, 3784-3789 (2017).
43. Allen, T. H., Kawamoto, T., Gardner, S., Geib, S. J. & Curran, D. P. N-heterocyclic carbene boryl iodides catalyze insertion reactions of N-heterocyclic carbene boranes and diazoesters. Org. Lett. 19, 3680-3683 (2017).
44. Wang, Z. J. et al. Improved cyclopropanation activity of histidine-ligated cytochrome P450 enables the enantioselective formal synthesis of levomilnacipran. Angew. Chem. Int. Ed. 53, 6810-6813 (2014).