Enzymatic basis of ribosomal peptide prenylation in cyanobacteria

Journal of the American Chemical Society

Volumn 133, Issue 34, 2011, Pages 13698-13705

  McIntosh, John A ^a   Donia, Mohamed S ^a   Nair, Satish K ^b   Schmidt, Eric W ^a  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS BUFFER; CLAISEN REARRANGEMENT; COMMON MODELS; CYCLIC PEPTIDES; ENZYME RECOGNITION; LEADER SEQUENCE; MACROCYCLICS; NATURAL PRODUCTS; PHENOLIC COMPOUNDS; POST-TRANSLATIONAL MODIFICATIONS; PRENYLATION; PRENYLTRANSFERASE; PROTEIN FAMILY; RIBOSOMAL PEPTIDES;

AMINO ACIDS; BIOCHEMISTRY; BIOSYNTHESIS; ENZYMES; PHENOLS;

PEPTIDES;

BACTERIAL ENZYME; BACTERIAL PROTEIN; CYCLOPEPTIDE; DIMETHYLALLYLTRANSFERASE; RIBOSOME PROTEIN; TYROSINE;

ARTICLE; BIOSYNTHESIS; CLAISEN REARRANGEMENT; CONTROLLED STUDY; CYANOBACTERIUM; ENZYME ACTIVITY; NONHUMAN; PROTEIN PRENYLATION;

AMINO ACID SEQUENCE; CYANOBACTERIA; DIMETHYLALLYLTRANSTRANSFERASE; GENE EXPRESSION; MOLECULAR SEQUENCE DATA; PEPTIDES; PHYLOGENY; PRENYLATION; RIBOSOMES;

EID: 80052087588     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205458h     Document Type: Article

References (57)

1. Brandt, W.; Bräuer, L.; Günnewich, N.; Kufka, J.; Rausch, F.; Schulze, D.; Schulze, E.; Weber, R.; Zakharova, S.; Wessjohann, L. Phytochemistry 2009, 70, 1758-1775
2. Nguyen, U. T.; Goody, R. S.; Alexandrov, K. ChemBioChem 2010, 11, 1194-1201
3. Gibbs, R. A. Nat. Chem. Biol. 2005, 1, 7-8
4. Casey, P. J.; Seabra, M. C. J. Biol. Chem. 1996, 271, 5289-5292
5. Sacchettini, J. C.; Poulter, C. D. Science 1997, 277, 1788-1789
6. Edwards, D. J.; Gerwick, W. H. J. Am. Chem. Soc. 2004, 126, 11432-11433
7. Reiss, Y.; Goldstein, J. L.; Seabra, M. C.; Casey, P. J.; Brown, M. S. Cell 1990, 62, 81-88
8. Kuzuyama, T.; Noel, J. P.; Richard, S. B. Nature 2005, 435, 983-987
9. Gebler, J. C.; Poulter, C. D. Arch. Biochem. Biophys. 1992, 296, 308-313
10. Saleh, O.; Haagen, Y.; Seeger, K.; Heide, L. Phytochemistry 2009, 70, 1728-1738
11. Donia, M. S.; Ravel, J.; Schmidt, E. W. Nat. Chem. Biol. 2008, 4, 341-343
12. Carroll, A. R.; Coll, J. C.; Bourne, D. J.; MacLeod, J. K.; Zabriskie, T.; Ireland, C. M.; Bowden, B. F. Aust. J. Chem. 1996, 49, 659-667
13. Okada, M.; Sato, I.; Cho, S. J.; Iwata, H.; Nishio, T.; Dubnau, D.; Sakagami, Y. Nat. Chem. Biol. 2005, 1, 23-24
14. McIntosh, J. A.; Donia, M. S.; Schmidt, E. W. Nat. Prod. Rep. 2009, 26, 537-559
15. Donia, M. S.; Schmidt, E. W. Chem. Biol. 2011, 18, 508-519
16. Donia, M. S.; Hathaway, B. J.; Sudek, S.; Haygood, M. G.; Rosovitz, M. J.; Ravel, J.; Schmidt, E. W. Nat. Chem. Biol. 2006, 2, 729-735
17. Leikowski, N.; Fewer, D. P.; Sivonen, K. Appl. Environ. Microbiol. 2009, 75, 853-857
18. McIntosh, J. A.; Schmidt, E. W. ChemBioChem 2010, 11, 1413-1421
19. McIntosh, J. A.; Robertson, C. R.; Vinayak, A.; Satish, N. K.; Bulaj, G. W.; Schmidt, E. W. J. Am. Chem. Soc. 2010, 132, 15499-15501
20. McIntosh, J. A.; Donia, M. S.; Schmidt, E. W. J. Am. Chem. Soc. 2010, 132, 4089-4091
21. Lee, J.; McIntosh, J. A.; Hathaway, B. J.; Schmidt, E. W. J. Am. Chem. Soc. 2009, 131, 2122-2214
22. Quillinan, A. J.; Scheinmann, F. J. Chem. Soc. D 1971, 966-967
23. Tisdale, E. J.; Slobodov, I.; Theodorakis, E. A. Org. Biomol. Chem. 2003, 1, 4418-4422
24. Nicolaou, K. C.; Li, J. Angew. Chem., Int. Ed. 2001, 40, 4264-4268
25. Jost, M.; Zocher, G.; Tarcz, S.; Matuscheck, M.; Xie, X.; Li, S. M.; Stehle, T. J. Am. Chem. Soc. 2010, 132, 17849-17858
26. Haagen, Y.; Unsöld, I.; Westrich, L.; Gust, B.; Richard, S. B.; Noel, J. P.; Heide, L. FEBS Lett. 2007, 581, 2889-2893
27. Ding, Y.; de Wet, J. R.; Cavalcoli, J.; Li, S.; Greshock, T. J.; Miller, K. A.; Finefield, J. M.; Sunderhaus, J. D.; McAfoos, T. J.; Tsukamoto, S.; Williams, R. M.; Sherman, D. H. J. Am. Chem. Soc. 2010, 132, 12733-12740
28. Schultz, A. W.; Lewis, C. A.; Luzung, M. R.; Baran, P. S.; Moore, B. S. J. Nat. Prod. 2010, 73, 373-377
29. Balibar, C. J.; Howard-Jones, A. R.; Walsh, C. T. Nat. Chem. Biol. 2007, 3, 584-592
30. Pojer, F.; Wemakor, E.; Kammerer, B.; Chen, H.; Walsh, C. T.; Li, S. M.; Heide, L. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 2316-2321
31. Oman, T. J.; van der Donk, W. A. Nat. Chem. Biol. 2010, 6, 9-18
32. Murakami, M.; Itou, Y.; Ishida, K.; Shin, H. J. J. Nat. Prod. 1999, 62, 725-755
33. Ahmed, F.; Ohtsuki, T.; Aida, W.; Ishibashi, M. J. Nat. Prod. 2008, 71, 1963-1966
34. Gebler, J. C.; Woodside, A. B.; Poulter, C. D. J. Am. Chem. Soc. 1992, 114, 7354-7360
35. Donia, M. S.; Schmidt, E. W. Chem. Biol. 2011, 18, 508-519
36. Sobolev, V. S.; Potter, T. L.; Horn, B. W. Phytochem. Anal. 2006, 17, 312-322
37. Miranda, C. L.; Stevens, J. F.; Ivanov, V.; McCall, M.; Frei, B.; Deinzer, M. L.; Buhler, D. R. J. Agric. Food Chem. 2000, 48, 3876-3884
38. Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 9228-9229
39. Hoarau, C.; Pettus, R. R. T. Synlett 2003, 127-137
40. Bagnell, L.; Cablewski, T.; Strauss, C. R.; Trainor, R. W. J. Org. Chem. 1996, 61, 7355-7359
41. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275-3279
42. Majumdar, K. C.; Alam, S.; Chattopadhyay, B. Tetrahedron 2008, 64, 597-643
43. Knowles, J. R.; Copley, S. D. J. Am. Chem. Soc. 1987, 109, 5008-5013
44. Grieco, P. A. Aldrichimica Acta 1991, 24, 59-66
45. White, W. N.; Wolfarth, E. U. J. Org. Chem. 1970, 35, 2196-2199
46. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735-1766
47. Harfenist, M.; Thom, E. J. Org. Chem. 1972, 37, 841-848
48. Goering, H. L.; Jacobson, R. R. J. Am. Chem. Soc. 1958, 80, 3277-3285
49. Zou, H. X.; Xie, X.; Zheng, X. D.; Li, S. M. Appl. Microbiol. Biotechnol. 2011, 89, 1443-1451
50. Donia, M. S.; Schmidt, E. W. Comprehensive Natural Products Chemistry II; Mander, L.; Liu, H.-W., Eds.; Elsevier: Oxford, U.K., 2008; Vol. 2, pp 539-558.
51. Kremer, A.; Li, S. M. Microbiology 2010, 156, 278-286
52. Uyeda, C.; Rötheli, A. R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 9753-9756
53. Andrews, P. R.; Smith, G. D.; Young, I. G. Biochemistry 1973, 12, 3492-3498
54. Woodside, A. B.; Huang, Z.; Poulter, C. D. Org. Synth. 1988, 66, 211-215
55. Woodside, A. B.; Huang, Z.; Poulter, C. D. Org. Synth. 1993, 8, 616-620
56. Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1986, 51, 4768-4779
57. Stankova, I. G.; Videnov, G. I.; Golovinsky, E. V.; Jung, G. J. Peptide Sci. 1999, 5, 392-398