Synthesis and biological studies of 35-deoxy amphotericin B methyl ester

Angewandte Chemie - International Edition

Volumn 47, Issue 23, 2008, Pages 4339-4342

  Szpilman, Alex M ^a   Manthorpe, Jeffrey M ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Amphotericin B; Antifungal agents; Mechanism of action; Natural products; Total synthesis

Indexed keywords

ESTERIFICATION; ESTERS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

AMPHOTERICIN B; ANTIFUNGAL AGENTS; MECHANISM OF ACTION; NATURAL PRODUCTS; TOTAL SYNTHESIS;

COMPLEXATION;

AMPHOTERICIN B; ANTIFUNGAL AGENT; DRUG DERIVATIVE; GLYCOSIDE; ION CHANNEL;

ARTICLE; CANDIDA ALBICANS; CELL MEMBRANE; CHEMISTRY; DRUG EFFECT; HYDROGEN BOND; SACCHAROMYCES CEREVISIAE; SYNTHESIS; TECHNIQUE;

AMPHOTERICIN B; ANTIFUNGAL AGENTS; CANDIDA ALBICANS; CELL MEMBRANE; GLYCOSIDES; HYDROGEN BONDING; ION CHANNELS; METHODS; SACCHAROMYCES CEREVISIAE;

EID: 46749087921     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800590     Document Type: Article

References (28)

1. A. M. Szpilman, D. M. Cereghetti, N. R. Wurtz, J. M. Manthorpe, E. M. Carreira, Angew. Chem. 2008, DOI: 10.1002/ange.200800589;
2. Angew. Chem. Int. Ed. 2008, DOI: 10.1002/anie.200800589.
3. S. C. Hartsel, C. Hatch, W. Ayenew, J. Liposome Res. 1993, 3, 377-408, and references therein.
4. P. Ganis, G. Avitabile, W. Mechlin, C. P. Schaffner, J. Am. Chem. Soc. 1971, 93, 4560-4564.
5. M. Baginski, H. Resat, J. A. Mccammon, Mol. Pharmacol. 1997, 52, 560-570.
6. Macrolide Antibiotics, Chemistry, Biology and Practice (Ed.: S. Omura), Academic Press, New York, 1984.
7. a) A. V. Demchenko, Synlett 2003, 1225-1240;
8. b) E. S. H. El Ashry, N. Rashed, E. S. I. Ibrahim, Curr. Org. Synth. 2005, 2, 175-213.
9. a) K. C. Nicolaou, T. K. Chakraborty, Y. Ogawa, R. A. Daines, N. S. Simpkins, G. T. Furst, J. Am. Chem. Soc. 1988, 110, 4660-4672;
10. b) K. C. Nicolaou, R. A. Daines, Y. Ogawa, T. K. Chakraborty, J. Am. Chem. Soc. 1988, 110, 4696-4705.
11. a) R. L. Halcomb, S. J. Danishefsky, J. Am. Chem. Soc. 1989, 111, 6661-6666;
12. b) D. Kahne, S. Walker, Y. Cheng, D. Van Engen, J. Am. Chem. Soc. 1989, 111, 6881-6882;
13. c) G. K. Packard, S. D. Rychnovsky, Org. Lett. 2001, 3, 3393-3396.
14. a) N. K. Kochetkov, A. Y. Khorlin, A. F. Bochkov, Tetrahedron 1967, 23, 693-707;
15. b) for a recent review, see: F. Kong, Carbohydr. Res. 2007, 342, 345-373.
16. A related approach was recently published: H. Yu, D. L. Williams, H. E. Ensley, Tetrahedron Lett. 2005, 46, 3417-3421.
17. Glycoside tosylates are capable of glycosidating simple alcohols: R. Eby, C. Schuerch, Carbohydr. Res. 1974, 34, 79-90.
18. A mixture of epimers is formed during the azide reduction. The saponification of methyl esters of acetonide-protected derivatives of natural amphotericin B (1) leads to epimerization, in contrast to what is observed for amphotericin B methyl ester.
19. V. Paquet, A. A. Volmer, E. M. Carreira, Chem. Eur. J. 2008, 14, 2465-2481.
20. a) P. van Hoogevest, B. de Kruijff, Biochim. Biophys. Acta Biomembr. 1978, 511, 397-407;
21. b) D. S. Orlov, T. Nguyen, R. I. Lehrer, J. Microbiol. Methods 2002, 49, 325-328.
22. a) A. Zumbuehl, P. Stano, M. Sohrmann, T. Vigassy, E. Pretsch, M. Peter, P. Walde, D. Jeannerat, E. M. Carreira, Angew. Chem. 2004, 116, 5293-5297;
23. Angew. Chem. Int. Ed. 2004, 43, 5181-5185;
24. Angew. Chem. 2004, 116, 5293-5297;
25. b) A. Zumbuehl, P. Stano, M. Sohrmann, M. Peter, P. Walde, E. M. Carreira, Org. Biomol. Chem. 2007, 5, 1339-1342;
26. c) V. Paquet, A. Zumbuehl, E. M. Carreira, Bioconjugate Chem. 2006, 17, 1460-1463;
27. d) A. Zumbuehl, P. Stano, D. Heer, P. Walde, E. M. Carreira, Org. Lett. 2004, 6, 3683-3686.
28. The width of the phospholipid bilayer of these LUVs is 37 Å and thus any formation of single-barrel ion channels should be precluded. See the Supporting Information for additional measurements.