Total synthesis and biological evaluation of the antibiotic lysocin E and its enantiomeric, epimeric, and N-demethylated analogues

Angewandte Chemie - International Edition

Volumn 54, Issue 5, 2015, Pages 1556-1560

  Murai, Motoki ^a   Kaji, Takuya ^a   Kuranaga, Takefumi ^a   Hamamoto, Hiroshi ^a   Sekimizu, Kazuhisa ^a   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Antibiotics; Natural products; Solid phase synthesis; Structure activity relationships; Total synthesis

Indexed keywords

ANTIBIOTICS; BACTERIA; ENANTIOMERS;

ANTI-BACTERIAL ACTIVITY; BIOLOGICAL EVALUATION; CHIRAL RECOGNITION; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; NATURAL PRODUCTS; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ANTIINFECTIVE AGENT; COORDINATION COMPOUND; CYCLOPEPTIDE; LYSOCIN E; PALLADIUM;

CATALYSIS; CHEMISTRY; DRUG EFFECTS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TEST; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CATALYSIS; COORDINATION COMPLEXES; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS; PALLADIUM; PEPTIDES, CYCLIC; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84921523214     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410270     Document Type: Article

References (49)

1. a) F. D. Lowy, J. Clin. Invest. 2003, 111, 1265
2. b) The Antibiotic Alarm, Nature 2013, 495, 141.
3. a) A. Coates, Y. Hu, R. Bax, C. Page, Nat. Rev. Drug Discovery 2002, 1, 895
4. b) C. Walsh, Nat. Rev. Microbiol. 2003, 1, 65
5. c) M. S. Butler, M. A. Cooper, J. Antibiot. 2011, 64, 413
6. d) K. M. G. O'Connell, J. T. Hodgkinson, H. F. Sore, M. Welch, G. P. C. Salmond, D. R. Spring, Angew. Chem. Int. Ed. 2013, 52, 10706
7. Angew. Chem. 2013, 125, 10904.
8. H. Hamamoto, M. Urai, K. Ishii, J. Yasukawa, A. Paudell, M. Murai, T. Kaji, T. Kuranaga, K. Hamase, T. Katsu, J. Su, T. Adachi, R. Uchida, H. Tomoda, M. Yamada, M. Souma, H. Kurihara, M. Inoue, K. Sekimizu, Nat. Chem. Biol, DOI: 10.1038/NCHEMBIO.1710.
9. Z. Tynecka, Z. Szczesniak, A. Malm, R. Los, Res. Microbiol. 1999, 150, 555.
10. For reviews, see: a) D. J. Newman, G. M. Cragg, J. Nat. Prod. 2007, 70, 461
11. b) J. W.-H. Li, J. C. Vederas, Science 2009, 325, 161
12. c) P. A. Wender, V. A. Verma, T. J. Paxton, T. H. Pillow, Acc. Chem. Res. 2008, 41, 40
13. d) A. M. Szpilman, E. M. Carreira, Angew. Chem. Int. Ed. 2010, 49, 9592
14. Angew. Chem. 2010, 122, 9786
15. e) R. M. Wilson, S. J. Danishefsky, Angew. Chem. Int. Ed. 2010, 49, 6032
16. Angew. Chem. 2010, 122, 6168.
17. R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149.
18. For reviews, see: a) J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243
19. b) S. C. Stolze, M. Kaiser, Synthesis 2012, 44, 1755.
20. For recent accounts on SAR studies on peptidic natural products from our laboratory, see: a) H. Itoh, M. Inoue, Acc. Chem. Res. 2013, 46, 1567
21. b) M. Inoue, Proc. Jpn. Acad. Ser. B 2014, 90, 56.
22. For recent reviews on non-ribosomal peptides, see: a) S. A. Sieber, M. A. Marahiel, Chem. Rev. 2005, 105, 715
23. b) C. T. Walsh, R. V. O'Brien, C. Khosla, Angew. Chem. Int. Ed. 2013, 52, 7098
24. Angew. Chem. 2013, 125, 7238.
25. S. Wang, J. Am. Chem. Soc. 1973, 95, 1328.
26. L. A. Carpino, H. Shroff, S. A. Triolo, E. M. E. Mansour, H. Wenschuh, F. Albericio, Tetrahedron Lett. 1993, 34, 7829.
27. a) L. A. Carpino, G Y Han, J. Am. Chem. Soc. 1970, 92, 5748
28. b) Fmoc Solid Phase Peptide Synthesis - A Practical Approach (Eds.: W C. Chan, P.D. White), Oxford University Press, Oxford, 2000.
29. For related approaches to cyclic peptides, see: a) A. Trzeciak, W Bannwarth, Tetrahedron Lett. 1992, 33, 4557
30. b) S. A. Kates, N. A. Solé, C. R. Johnson, D. Hudson, G Barany, F Albericio, Tetrahedron Lett. 1993, 34, 1549
31. c) S. C. Stolze, M. Meltze, M. Ehrmann, M. Kaiser, Chem. Commun. 2010, 46, 8857
32. d) J. Lee, J. H. Griffin, T.I. Nicas, J. Org. Chem. 1996, 61, 3983
33. e) R. Krishnamoorthy, L. D. Vazquez-Serrano, J. A. Turk, J. A. Kowalski, A. G Benson, N. T. Breaux, M. A. Lipton, J. Am. Chem. Soc. 2006, 128, 15392
34. f) M. J. Dixon, A. Nathubhai, O. A. Andersen, D M. F van Aalten, I. M. Eggleston, Org. Biomol. Chem. 2009, 7, 259
35. g) T Walther, H.-D Arndt, H. Waldmann, Org. Lett. 2008, 10, 3199
36. h) M. Pelay-Gimeno, Y. García-Ramos, M. J. Martin, J. Spengler, J. M. Molina-Guijarro, S. Munt, A. M. Francesch, C. Cuevas, J. Tulla-Puche, F. Albericio, Nat. Commun. 2013, 4, 2352.
37. a) S. Mazur, P. Jayelekshmy, J. Am. Chem. Soc. 1979, 101, 677
38. for a review, see: b) C. J. White, A. K. Yudin, Nat. Chem. 2011, 509.
39. R. Noyori, T. Ohkuma, M. Kitamura, J. Am. Chem. Soc. 1987, 109, 5856.
40. L. Coutable, K. Adil, C. Saluzzo, Tetrahedron 2008, 64, 11296.
41. a) H.-M. Yu, S.-T. Chen, K.-T. Wang, J. Org. Chem. 1992, 57, 4781
42. b) S. A. Palasek, Z. J. Cox, J. M. Collins, J. Pept. Sci. 2007, 13, 143
43. c) B. Bacsa, K. Horváti, S. Bõsze, F. Andreae, C. O. Kappe, J. Org. Chem. 2008, 73, 7532.
44. V. Dourtoglou, B. Gross, V. Lambropoulou, C. Zioudrou, Synthesis 1984, 572.
45. S. Friedrich-Bochnitschek, H. Waldmann, H. Kunz, J. Org. Chem. 1989, 54, 751.
46. J. Coste, D. Le-Nguyen, B. Castro, Tetrahedron Lett. 1990, 31, 205.
47. a) J. Chatterjee, C. Gilon, A. Hoffman, H. Kessler, Acc. Chem. Res. 2008, 41, 1331
48. b) J. Chatterjee, F. Rechenmacher, H. Kessler, Angew. Chem. Int. Ed. 2013, 52, 254
49. Angew. Chem. 2013, 125, 268.