Quantifying Possible Routes for SpnF-Catalyzed Formal Diels-Alder Cycloaddition

Journal of the American Chemical Society

Volumn 139, Issue 11, 2017, Pages 3942-3945

  Medvedev, Michael G ^a,b   Zeifman, Alexey A ^b   Novikov, Fedor N ^b,c   Bushmarinov, Ivan S ^a   Stroganov, Oleg V ^b,c   Titov, Ilya Yu ^b,c   Chilov, Ghermes G ^b,c   Svitanko, Igor V ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c MolTech Ltd   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; CATALYSIS; ENZYMES; MECHANISMS; QUANTUM THEORY;

DIELS-ALDER CYCLOADDITIONS; DIELS-ALDER REACTION; ENZYMATIC REACTION; FIRST-ORDER APPROXIMATIONS; ORGANIC SYNTHESIS; QUANTUM MECHANICAL; REACTION CATALYZED; [4 + 2] CYCLOADDITION;

CYCLOADDITION;

ENZYME; SPINOSYN A; SPNF ENZYME; UNCLASSIFIED DRUG; WATER;

ARTICLE; BIOSYNTHESIS; CYCLOADDITION; DIELS ALDER REACTION; ENZYME ACTIVE SITE; ENZYME MECHANISM; QUANTUM MECHANICS; WATER FLOW;

EID: 85015881878     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b13243     Document Type: Article

References (29)

1. Nishiwaki, N. Methods and Applications of Cycloaddition Reactions in Organic Syntheses; John Wiley & Sons: Hoboken, NJ, 2013.
2. Preiswerk, N.; Beck, T.; Schulz, J. D.; Milovník, P.; Mayer, C.; Siegel, J. B.; Baker, D.; Hilvert, D. Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 8013-8018 10.1073/pnas.1401073111
3. Guimarães, C. R. W.; Udier-Blagović, M.; Jorgensen, W. L. J. Am. Chem. Soc. 2005, 127, 3577-3588 10.1021/ja043905b
4. Klas, K.; Tsukamoto, S.; Sherman, D. H.; Williams, R. M. J. Org. Chem. 2015, 80, 11672-11685 10.1021/acs.joc.5b01951
5. Minami, A.; Oikawa, H. J. Antibiot. 2016, 69, 500-506 10.1038/ja.2016.67
6. Byrne, M. J.; Lees, N. R.; Han, L.-C.; van der Kamp, M. W.; Mulholland, A. J.; Stach, J. E. M.; Willis, C. L.; Race, P. R. J. Am. Chem. Soc. 2016, 138, 6095-6098 10.1021/jacs.6b00232
7. Li, L.; Yu, P.; Tang, M.-C.; Zou, Y.; Gao, S.-S.; Hung, Y.-S.; Zhao, M.; Watanabe, K.; Houk, K. N.; Tang, Y. J. Am. Chem. Soc. 2016, 138, 15837-15840 10.1021/jacs.6b10452
8. Kim, H. J.; Ruszczycky, M. W.; Choi, S.; Liu, Y.; Liu, H. Nature 2011, 473, 109-112 10.1038/nature09981
9. Yano, B. L.; Bond, D. M.; Novilla, M. N.; McFadden, L. G.; Reasor, M. J. Toxicol. Sci. 2002, 65, 288-298 10.1093/toxsci/65.2.288
10. Gordeev, E. G.; Ananikov, V. P. PLoS One 2015, 10, e0119984 10.1371/journal.pone.0119984
11. Hess, B. A., Jr.; Smentek, L. Org. Biomol. Chem. 2012, 10, 7503-7509 10.1039/c2ob25827g
12. Patel, A.; Chen, Z.; Yang, Z.; Gutiérrez, O.; Liu, H.; Houk, K. N.; Singleton, D. A. J. Am. Chem. Soc. 2016, 138, 3631-3634 10.1021/jacs.6b00017
13. Kim, N. H. Ph.D. Dissertation, The University of Texas at Austin, Austin, TX, 2013.
14. Black, K.; Liu, P.; Xu, L.; Doubleday, C.; Houk, K. N. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 12860-12865 10.1073/pnas.1209316109
15. Rogers, D. W.; Matsunaga, N.; Zavitsas, A. A. J. Org. Chem. 2006, 71, 2214-2219 10.1021/jo051358m
16. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241 10.1007/s00214-007-0310-x
17. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261 10.1063/1.1677527
18. Peverati, R.; Truhlar, D. G. Philos. Trans. R. Soc., A 2014, 372, 20120476 10.1098/rsta.2012.0476
19. Linder, M.; Brinck, T. Phys. Chem. Chem. Phys. 2013, 15, 5108-5114 10.1039/c3cp44319a
20. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158-6170 10.1063/1.478522
21. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104 10.1063/1.3382344
22. Medvedev, M. G.; Bushmarinov, I. S.; Sun, J.; Perdew, J. P.; Lyssenko, K. A. Science 2017, 355, 49-52 10.1126/science.aah5975
23. Watts, K. S.; Dalal, P.; Tebben, A. J.; Cheney, D. L.; Shelley, J. C. J. Chem. Inf. Model. 2014, 54, 2680-2696 10.1021/ci5001696
24. McGill, R.; Tukey, J. W.; Larsen, W. A. Am. Stat. 1978, 32, 12 10.1080/00031305.1978.10479236
25. Yu, P.; Patel, A.; Houk, K. N. J. Am. Chem. Soc. 2015, 137, 13518-13523 10.1021/jacs.5b06656
26. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, 1994.
27. Seeman, J. I. J. Chem. Educ. 1986, 63, 42 10.1021/ed063p42
28. Medford, A. J.; Wellendorff, J.; Vojvodic, A.; Studt, F.; Abild-Pedersen, F.; Jacobsen, K. W.; Bligaard, T.; Nørskov, J. K. Science 2014, 345, 197-200 10.1126/science.1253486
29. Sadovnichy, V.; Tikhonravov, A.; Voevodin, V.; Opanasenko, V. “Lomonosov”: Supercomputing at Moscow State University. In Contemporary High Performance Computing: from Petascale toward Exascale; Chapman & Hall/CRC Computational Science; CRC Press: Boca Raton, FL, 2013; pp 283-307.