Experimental lineage and functional analysis of a remotely directed peptide epoxidation catalyst

Journal of the American Chemical Society

Volumn 136, Issue 14, 2014, Pages 5301-5308

  Lichtor, Phillip A ^a   Miller, Scott J ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDES;

DIRECTING GROUPS; EPOXIDATION CATALYSTS; FARNESOL; MODIFIED CATALYSTS; N-TERMINALS; NMR STUDIES; SELECTIVE EPOXIDATION; SIDE-CHAINS;

CATALYST SELECTIVITY;

FARNESOL; EPOXIDE; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CATALYST; CONFORMATION; CONFORMATIONAL TRANSITION; ENANTIOSELECTIVITY; EPOXIDATION; HYDROGEN BOND; PEPTIDE ANALYSIS; PEPTIDE LIBRARY; PROTEIN SECONDARY STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CATALYSIS; EPOXY COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PEPTIDES;

EID: 84897975989     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja410567a     Document Type: Article

References (54)

1. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370
2. Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450-2494
3. Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299
4. Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 4389-4391
5. Malkov, A. V.; Czemerys, L.; Malyshev, D. A. J. Org. Chem. 2009, 74, 3350-3355
6. Egami, H.; Oguma, T.; Katsuki, T. J. Am. Chem. Soc. 2010, 132, 5886-5895
7. Zhang, W.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 286-287
8. Zhi, L.; Wei, Z.; Yamamoto, H. Angew. Chem., Int. Ed. 2008, 47, 7520-7522
9. Olivares-Romero, J. L.; Zhi, L.; Yamamoto, H. J. Am. Chem. Soc. 2013, 135, 3411-3413
10. Li, Z.; Yamamoto, H. J. Am. Chem. Soc. 2010, 132, 7878-7880
11. Leow, D.; Li, G.; Mei, T.-S.; Yu, J.-Q. Nature 2012, 486, 518-522
12. Tang, R.-Y.; Li, G.; Yu, J.-Q. Nature 2014, 507, 215-220
13. Breslow, R.; Maresca, L. M. Tetrahedron Lett. 1977, 18, 623-626
14. Breslow, R.; Maresca, L. M. Tetrahedron Lett. 1978, 19, 887-890
15. Das, S.; Incarvito, C. D.; Crabtree, R. H.; Brudvig, G. W. Science 2006, 312, 1941-1943
16. Li, J.-J.; Giri, R.; Yu, J.-Q. Tetrahedron 2008, 64, 6979-6987
17. Lichtor, P. A.; Miller, S. J. Nat. Chem. 2012, 4, 990-995
18. Lichtor, P. A.; Miller, S. J. ACS Comb. Sci. 2011, 13, 321-326
19. Peris, G.; Jakobsche, C. E.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 8710-8711
20. Lam, K. S.; Lebl, M.; Krchnák, V. Chem. Rev. 1997, 97, 411-448
21. Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. Int. J. Pept. Protein Res. 1991, 37, 487-493
22. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84
23. Taylor, S. J.; Morken, J. P. Science 1998, 280, 267-270
24. Krattiger, P.; McCarthy, C.; Pfaltz, A.; Wennemers, H. Angew. Chem., Int. Ed. 2003, 42, 1722-1724
25. Lingard, I.; Bhalay, G.; Bradley, M. Chem. Commun. 2003, 2310-2311
26. Clouet, A.; Darbe, T.; Reymond, J.-L. Angew. Chem., Int. Ed. 2004, 43, 4612-4615
27. Krattiger, P.; Kovasy, R.; Revell, J. D.; Ivan, S.; Wennemers, H. Org. Lett. 2005, 7, 1101-1103
28. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496-6502
29. Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221-232
30. Haque, T. S.; Littler, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975-6985
31. Miller, S. J. Acc. Chem. Res. 2004, 37, 601-610 and references therein
32. Angione, M. C.; Miller, S. J. Tetrahedron 2006, 62, 5254-5261
33. Blank, J. T.; Miller, S. J. Biopolymers 2006, 84, 38-47
34. Lewis, C. A.; Miller, S. J. Angew. Chem., Int. Ed. 2006, 45, 5616-5619
35. Cowen, B. J.; Saunders, L. B.; Miller, S. J. J. Am. Chem. Soc. 2009, 131, 6105-6107
36. Lewis, C. A.; Longcore, K. E.; Miller, S. J.; Wender, P. A. J. Nat. Prod. 2009, 72, 1864-1869
37. Fowler, B. S.; Mikochik, P. J.; Miller, S. J. J. Am. Chem. Soc. 2010, 132, 2870-2871
38. Fowler, B. S.; Laemmerhold, K. M.; Miller, S. J. J. Am. Chem. Soc. 2012, 134, 9755-9761
39. Barrett, K. T.; Miller, S. J. J. Am. Chem. Soc. 2013, 135, 2963-2966
40. Linton, B. R.; Reutershan, M. H.; Aderman, C. M.; Richardson, E. A.; Brownell, K. R.; Ashley, C. W.; Evans, C. A.; Miller, S. J. Tetrahedron Lett. 2007, 48, 1993-1997
41. Akagawa, K.; Akabane, H.; Sakamoto, S.; Kudo, K. J. Org. Chem. 2008, 10, 2035-2037
42. Wu, F.-C.; Da, C.-S.; Du, Z.-X.; Guo, Q.-P.; Li, W.-P.; Yi, L.; Jia, Y.-N.; Ma, X. J. Org. Chem. 2009, 74, 4812-4818
43. Akagawa, K.; Suzuki, R.; Kudo, K. Adv. Synth. Catal. 2012, 354, 1280-1286
44. Mahajan, M.; Bhattacharjya, S. Angew. Chem., Int. Ed. 2013, 52, 6430-6434
45. Du, Z.-X.; Zhang, L.-Y.; Fan, X.-Y.; Wu, F.-C.; Da, C.-S. Tetrahedron Lett. 2013, 54, 2828-2832
46. Bryan, P.; Pantoliano, M. W.; Quill, S. G.; Hsiu, H.-Y.; Poulos, T. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 3743-3745
47. Brünger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J.-S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Acta Crystallogr. 1998, D54, 905-921
48. Brünger, A. T. Nat. Protoc. 2007, 2, 2728-2733
49. Halpern, J. Science 1982, 217, 401-407
50. Milner-White, E. J.; Ross, B. M.; Ismail, R.; Belhadj-Mostefa, K.; Poet, R. J. Mol. Biol. 1988, 204, 777-782
51. Henbest, H. B.; Wilson, R. A. L. Chem. Ind. 1956, 26, 659
52. Uppenberg, J.; Öhrner, N.; Norin, M.; Hult, K.; Kleywegt, G. J.; Patkar, S.; Waagen, V.; Anthonsen, T.; Jones, T. A. Biochemistry 1995, 34, 16838-16851
53. Magnusson, A.; Hult, K.; Holmquist, M. J. Am. Chem. Soc. 2001, 123, 4354-4355
54. Knowles, R. R.; Jacobsen, E. N. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20678