Total synthesis and complete structural assignment of Yaku'amide A

Journal of the American Chemical Society

Volumn 135, Issue 14, 2013, Pages 5467-5474

  Kuranaga, Takefumi ^a   Sesoko, Yusuke ^a   Sakata, Komei ^a   Maeda, Naoya ^a   Hayata, Atsushi ^a   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID RESIDUES; BIOLOGICAL ASSAYS; CONFORMATIONAL PROPERTIES; CROSS COUPLING REACTIONS; DEHYDROAMINO ACID; PEPTIDE SEQUENCES; STRUCTURAL ASSIGNMENTS; SYNTHETIC METHODOLOGY;

AMINO ACIDS; PEPTIDES; STEREOCHEMISTRY; STEREOSELECTIVITY;

AMIDES;

AMIDE; AMINE; AMINO ACID; CYTOTOXIN; DIOXANE; TETRAPEPTIDE; UNCLASSIFIED DRUG; YAKU AMIDE A;

AMIDATION; AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS COUPLING REACTION; CYTOTOXICITY; DEHYDRATION; ENANTIOMER; EPIMER; EPIMERIZATION; HYDROGENATION; HYDROGENOLYSIS; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTEIN STRUCTURE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; SYNTHESIS;

MOLECULAR STRUCTURE; OLIGOPEPTIDES;

EID: 84876028199     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja401457h     Document Type: Article

References (70)

1. Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897
2. Fusetani, N.; Matsunaga, S. Chem. Rev. 1993, 93, 1793
3. Bewley, C. A.; Faulkner, D. J. Angew. Chem., Int. Ed. 1998, 37, 2162
4. Blunt, J. W.; Copp, B. R.; Keyzers, R. A.; Munro, M. H. G.; Prinsep, M. R. Nat. Prod. Rep. 2012, 29, 144
5. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2007, 70, 461
6. Butler, M. S. Nat. Prod. Rep. 2008, 25, 475
7. Cragg, G. M.; Grothaus, P. G.; Newman, D. J. Chem. Rev. 2009, 109, 3012
8. Mishra, B. B.; Tiwari, V. K. Eur. J. Med. Chem. 2011, 46, 4769
9. Sieber, S. A.; Marahiel, M. A. Chem. Rev. 2005, 105, 715
10. McIntosh, J. A.; Donia, M. S.; Schmidt, E. W. Nat. Prod. Rep. 2009, 26, 537
11. Arnison, P. G.; Bibb, M. J.; Bierbaum, G.; Bowers, A. A.; Bugni, T. S.; Bulaj, G.; Camarero, J. A.; Campopiano, D. J.; Challis, G. L.; Clardy, J.; Cotter, P. D.; Craik, D. J.; Dawson, M.; Dittmann, E.; Donadio, S.; Dorrestein, P. C.; Entian, K.-D.; Fischbach, M. A.; Garavelli, J. S.; Göransson, U.; Gruber, C. W.; Haft, D. H.; Hemscheidt, T. K.; Hertweck, C.; Hill, C.; Horswill, A. R.; Jaspars, M.; Kelly, W. L.; Klinman, J. P.; Kuipers, O. P.; Link, A. J.; Liu, W.; Marahiel, M. A.; Mitchell, D. A.; Moll, G. N.; Moore, B. S.; Müller, R.; Nair, S. K.; Nes, I. F.; Norris, G. E.; Olivera, B. M.; Onaka, H.; Patchett, M. L.; Piel, J.; Reaney, M. J. T.; Rebuffat, S.; Ross, R. P.; Sahl, H.-G.; Schmidt, E. W.; Selsted, M. E.; Severinov, K.; Shen, B.; Sivonen, K.; Smith, L.; Stein, T.; Süssmuth, R. D.; Tagg, J. R.; Tang, G.-L.; Truman, A. W.; Vederas, J. C.; Walsh, C. T.; Walton, J. D.; Wenzel, S. C.; Willey, J. M.; van der Donk, W. A. Nat. Prod. Rep. 2013, 30, 108
12. Ueoka, R.; Ise, Y.; Ohtsuka, S.; Okada, S.; Yamori, T.; Matsunaga, S. J. Am. Chem. Soc. 2010, 132, 17692
13. Shimada, N.; Morimoto, K.; Naganawa, H.; Takita, T.; Hamada, M.; Maeda, K.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1981, 34, 1613
14. Shiroza, T.; Ebisawa, N.; Furihata, K.; Endo, T.; Seto, H.; Otake, N. Agric. Biol. Chem. 1982, 46, 865
15. Culvenor, C. C. J.; Cockrum, P. A.; Edgar, J. A.; Frahn, J. L.; Gorst-Allman, C. P.; Jones, A. J.; Marasas, W. F. O.; Murray, K. E.; Smith, L. W.; Steyn, P. S.; Vleggaar, R.; Wessels, P. L. J. Chem. Soc., Chem. Commun. 1983, 1259
16. Zenkoh, T.; Ohtsu, Y.; Yoshimura, S.; Shigematsu, N.; Takase, S.; Hino, M. J. Antibiot. 2003, 56, 694
17. Rajashankar, K. R.; Ramakumar, S.; Jain, R. M.; Chauhan, V. S. J. Am. Chem. Soc. 1995, 117, 11773
18. Thormann, M.; Hofmann, H.-J. J. Mol. Struct (Theochem) 1998, 431, 79
19. Siodłak, D.; Grondys, J.; Lis, T.; Bujak, M.; Broda, M. A.; Rzeszotarska, B. J. Pept. Sci. 2010, 16, 496
20. Rich, D. H.; Bhatnager, P. K. J. Am. Chem. Soc. 1978, 100, 2212
21. Ward, D. E.; Vázquez, A.; Pedras, M. S. C. J. Org. Chem. 1999, 64, 1657
22. Yamori, T. Cancer Chemother. Pharmacol. 2003, 52, S74
23. Yaguchi, S.; Fukui, Y.; Koshimizu, I.; Yoshimi, H.; Matsuno, T.; Gouda, H.; Hirono, S.; Yamazaki, K.; Yamori, T. J. Natl. Cancer Inst. 2006, 98, 545
24. Yamori, T.; Matsunaga, A.; Sato, S.; Yamazaki, K.; Komi, A.; Ishizu, K.; Mita, I.; Edatsugi, H.; Matsuba, Y.; Takezawa, K.; Nakanishi, O.; Kohno, H.; Nakajima, Y.; Komatsu, H.; Andoh, T.; Tsuruo, T. Cancer Res. 1999, 59, 4042
25. Hamada, T.; Matsunaga, S.; Yano, G.; Fusetani, N. J. Am. Chem. Soc. 2005, 127, 110
26. Inoue, M.; Shinohara, N.; Tanabe, S.; Takahashi, T.; Okura, K.; Itoh, H.; Mizoguchi, Y.; Iida, M.; Lee, N.; Matsuoka, S. Nat. Chem. 2010, 2, 280
27. Matsuoka, S.; Shinohara, N.; Takahashi, T.; Iida, M.; Inoue, M. Angew. Chem., Int. Ed. 2011, 50, 4879
28. Shinohara, N.; Itoh, H.; Matsuoka, S.; Inoue, M. ChemMedChem 2012, 7, 1770
29. Itoh, H.; Matsuoka, S.; Kreir, M.; Inoue, M. J. Am. Chem. Soc. 2012, 134, 14011
30. Although the biosynthesis of yaku'amides is not elucidated, Piel and co-workers suggested a ribosomal origin of yaku'amides. They proved that polytheonamide B is a posttranslationally modified ribosomal peptide. Freeman, M. F.; Gurgui, C.; Helf, M. J.; Morinaka, B. I.; Uria, A. R.; Oldham, N. J.; Sahl, H.-G.; Matsunaga, S.; Piel, J. Science 2012, 338, 387
31. Ma, Z.; Naylor, B. C.; Loertscher, B. M.; Hafen, D. D.; Li, J. M.; Castle, S. L. J. Org. Chem. 2012, 77, 1208
32. Saavedra, C. J.; Boto, A.; Hernández, R. Org. Lett. 2012, 14, 3788
33. Hamphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243
34. Bonauer, C.; Walenzyk, T.; König, B. Synthesis 2006, 1
35. Nakamura, Y.; Ito, A.; Shin, C. Bull. Chem. Soc. Jpn. 1994, 67, 2151
36. Stohlmeyer, M. M.; Tanaka, H.; Wandless, T. J. J. Am. Chem. Soc. 1999, 121, 6100
37. Shangguan, N.; Joullié, M. Tetrahedron Lett. 2009, 50, 6748
38. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
39. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450
40. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13
41. Shen, R.; Lin, C. T.; Porco, J. A., Jr. J. Am. Chem. Soc. 2002, 124, 5650
42. Fürstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286
43. Dias, L. C.; de Oliveira, L. G.; Vilcachagua, J. D.; Nigsch, F. J. Org. Chem. 2005, 70, 2225
44. Okamoto, K.; Sakagami, M.; Feng, F.; Togame, H.; Takemoto, H.; Ichikawa, S.; Matsuda, A. Org. Lett. 2011, 13, 5240
45. For related examples, see: Cesati, R. R., III; Dwyer, G.; Jones, R. C.; Hayes, M. P.; Yalamanchili, P.; Casabier, D. S. Org. Lett. 2007, 9, 5617
46. Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851
47. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421
48. Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667
49. Li, P.; Evans, C. D.; Wu, Y.; Cao, B.; Hamel, E.; Joullié, M. M. J. Am. Chem. Soc. 2008, 130, 2351
50. Dettwilter, J. E.; Lubell, W. D. J. Org. Chem. 2003, 68, 177 see also ref 9b
51. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155
52. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277
53. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091
54. Andrés, J. M.; Manzano, R.; Pedrosa, R. Chem.-Eur. J. 2008, 14, 5116
55. Gagnier, S. V.; Larock, R. C. J. Org. Chem. 2000, 65, 1525
56. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205
57. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397
58. Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120
59. Evans, D. A.; Starr, J. T. J. Am. Chem. Soc. 2003, 125, 13531
60. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559
61. Prashad, M.; Har, D.; Kim, H.-Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067
62. Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853
63. Yabuuchi, T.; Kusumi, T. J. Org. Chem. 2000, 65, 397
64. Takano, S.; Akiyama, Y.; Sato, S.; Ogasawara, K. Chem. Lett. 1983, 12, 1593
65. Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412
66. Watanabe, T.; Imaizumi, T.; Chinen, T.; Nagumo, Y.; Shibuya, M.; Usui, T.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2010, 12, 1040
67. Lucey, C.; Kelly, S. A.; Mann, J. Org. Biomol. Chem. 2007, 5, 301
68. Avenoza, A.; Barriobero, J.; Busto, J. H.; Cativiela, C.; Peregrina, J. M. Tetrahedron Asymmetry 2002, 13, 625
69. PyBOP was utilized for condensation reactions of the α,β- unsaturated acids in order to avoid the undesired nucleophilic addition of the amine to the coupling reagent. For an example of the related undesired reaction, see: Story, S. C.; Aldrich, J. V. Int. J. Peptide Protein Res. 1994, 43, 292
70. El-Faham, A.; Subiós-Funosas, R.; Prohens, R.; Albericio, F. Chem.-Eur. J. 2009, 15, 9404