Total synthesis of proximicin A - C and synthesis of new furan-based DNA binding agents

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2804-2807

  Wolter, Falko E ^a   Schneider, Kathrin ^a   Davies, Brian P ^a   Socher, Elke R ^b   Nicholson, Graeme ^c   Seitz, Oliver ^b   Süssmuth, Roderich D ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

^c UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CONGOCIDINE; DISTAMYCIN A; DNA; DRUG DERIVATIVE; FURAN; FURAN DERIVATIVE; NYLON; PROXIMICIN A; PROXIMICIN B; PROXIMICIN C;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; SYNTHESIS;

AMINO ACIDS; DISTAMYCINS; DNA; FURANS; MOLECULAR STRUCTURE; NETROPSIN; NYLONS;

EID: 67649482474     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901003p     Document Type: Article

References (27)

1. (a) Finlay, A. C.; Hochstein, F. A.; Sobin, B. A.; Murphy, F. X. J. Am. Chem. Soc. 1951, 73, 341-343.
2. (b) Arcamone, F.; Penco, S.; Orezzi, P.; Nicolella, V.; Pirelli, A. Nature 1964, 203, 1064-1065.
3. (c) Zimmer, C.; Wahnert, U. Prog. Biophys. Mol. Biol. 1986, 47, 31-112.
4. (a) Bailly, C.; Chaires, J. B. Bioconjug. Chem. 1998, 9, 513-538.
5. (b) Dervan, P. B.; Poulin-Kerstien, A. T.; Fechter, E. J.; Edelson, B. S. Top. Curr. Chem. 2005, 253, 1-31.
6. (c) Lown, J. W. J. Mol. Recognit. 1994, 7, 79-88.
7. (d) Wemmer, D. E. Annu Rev. Biophys. Biomol. Struct. 2000, 29, 439-461.
8. (e) Dervan, P. B. Bioorg Med. Chem. 2001, 9, 2215-2235.
9. (f) Boger, D. L.; Fink, B. E.; Hedrick, M. P. J. Am. Chem. Soc. 2000, 122, 6382-6394. Incorporation of a 2,5-disubstituted furan amino acid:
10. (g) Lee, M.; Krowicki, K.; Shea, R. G.; Lown, J. W.; Pon, R. T. J. Mol. Recogn. 1989, 2, 84-93.
11. (a) Schneider, K.; Keller, S.; Wolter, F. E.; Roeglin, L.; Beil, W.; Seitz, O.; Nicholson, G.; Bruntner, C.; Riedlinger, J.; Fiedler, H.-P.; Süssmuth, R. D. Angew. Chem., Int. Ed. 2008, 47, 3258-3261.
12. (b) Fiedler, H.-P.; Bruntner, C.; Riedlinger, J.; Bull, A. T.; Knutsen, G.; Goodfellow, M.; Jones, A.; Maldonado, L.; Pathom-Aree, W.; Beil, W.; Schneider, K.; Keller, S.; Süssmuth, R. D. J. Antibiot. 2008, 61, 158-163.
13. Wolter, F. E.; Molinari, L.; Socher, E. R.; Schneider, K.; Nicholson, G.; Beil, W.; Seitz, O.; Süssmuth, R. D. Bioorg. Med. Chem. Lett. 2009, doi: 10.1016/j.bmcl.2009.04.042.
14. (a) Lee, H. K.; Chan, K. F.; Hui, C. W.; Yim, H. K.; Wu, X. W.; Wong, H. N. C. Pure Appl. Chem. 2005, 77, 139-143.
15. (b) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076-2080.
16. (c) Keay, B. A. Chem. Soc. Rev. 1999, 28, 209-215.
17. (d) Jeevanandam, A.; Ghule, A.; Ling, Y. C Curr. Org. Chem. 2002, 6, 841-864.
18. (e) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955-2020.
19. (f) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1999, 2849-2866.
20. (g) Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850-852.
21. Lee, G. C. M.; Holmes, J. M.; Harcourt, D. A.; Garst, M. E. J. Org. Chem. 1992, 57, 3126-3131.
22. (a) Taylor, J. S.; Schultz, P. G.; Dervan, P. B. Tetrahedron 1984, 40, 457-465.
23. (b) Yamamoto, Y.; Kimachi, T.; Kanaoka, Y.; Kato, S.; Bessho, K.; Matsumoto, T.; Kusakabe, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 7801-7804.
24. Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804-3805.
25. (a) Boger, D. L.; Fink, B. E.; Brunette, S. R.; Tse, W. C.; Hedrick, M. P. J. Am. Chem. Soc. 2001, 123, 5878-5891.
26. (b) Satz, A. L.; Bruice, T. C. Bioorg. Med. Chem. 2000, 8, 1871-1880.
27. Kopka, M. L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R. E. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 1376-1380.