A post-PKS oxidation of the amphotericin B skeleton predicted to be critical for channel formation is not required for potent antifungal activity.

نویسندگان

  • Daniel S Palacios
  • Thomas M Anderson
  • Martin D Burke
چکیده

(4e) Zumbuehl, A.; Jeannerat, D.; Martin, S.E.; Sohrmann, M.; Stano, P.; Vigassy, T.; Clark, D.D.; Hussey, S.L.; Peter, M.; Peterson, B.R.; Pretsch, E.; Walde, P.; Carreira, E.M. Angew. Chem. Int. Ed. 2004, 43, 5181-5185. (7b) Baginski, M.; Resat, H.; McCammon, J.A. Mol. Pharmacol. 1997, 52, 560-570. (8) (a) McNamara, C.M.; Box, S.; Crawforth, J.M.; Hickman, B.S.; Norwood, T.J.; Rawlings, B.J. J. Chem. Soc. Perkin Trans. 1 1998, 83-87. (b) Caffrey, P.; Lynch, S.; Flood, E. Finnan, S.; Oliynyk, M. Chem. Biol. 2001, 8, 713723. (10) (a) Chéron, M.; Cybulska, B.; Mazerski, J.; Grzybowska, J.; Czerwinski, A.; Borowski, E. Biochem. Pharmacol. 1988, 37, 827-836. (b) Matsumori, N.; Yamaji, N.; Matsuoka, S.; Oishi, T.; Murata, M. J. Am. Chem. Soc. 2002, 124, 4180-4181. (e) Umegawa, Y.; Matsumori, N.; Oishi, T.; Murata, M. Tetrahedron Lett. 2007, 48, 3393-3396. (13) (a) Nicolaou, K.C.; Chakraborty, T.K.; Ogawa, Y.; Daines, R.A.; Simpkins, N.S.; Furst, G.T. J. Am. Chem. Soc. 1988, 110, 4660-4672. (b) A degradative synthesis of 4 is described in the patent literature: Driver, M.J.; Greenless, A.R.; and MacPherson, D.T. U.S. Patent # 5,204,330, 1993. (c) MacPherson, D.T.; Corbett, D.F.; Costello, B.C.; Driver, M.J.; Greenless, A.R.; Maclachlan, W.S.; Shanks, C.T.; Taylor, A.W. Adventures in Polyene Macrolide Chemistry :The Derivatisation of Amphotericin B. In Recent Advances in the Chemistry of Anti-Infective Agents; Bently P.H. and Ponsford, R. Eds.; Royal Society of Chemistry : Cambridge, 1993; Special Publication No. 119, pp 205-222. (d) An impure sample of 4 was prepared via genetic engineering of the producer: Carmody, M.; Murphy, B.; Byrne, B.; Power, P.; Rai, D.; Rawlings, B.; Caffrey, P. J. Biol. Chem. 2005, 280, 34420-34426. (15) Garegg, P.J.; Samuelsson, B.; J. Chem. Soc., Perkin Trans. I 1980, 2866-2869. (18) Hutchins, R.O.; Kandasamy, D.; Dux, F.; Maryanoff, C.A.; Rotstein, D.; Goldsmith, B.; Burgoyne, W.; Cistone, F.; Dalessandro, J.; Puglis, J. J. Org. Chem. 1978, 43, 2259-2267. (19) (a) Sowinski, P.; Pawlak, J.; Borowski, E.; Gariboldi, P. Magn. Res. Chem. 1992, 30, 275-279. (24) Fujii, G.; Chang, J.-E.; Coley, T.; Steere, B. Biochemistry 1997, 36, 4959-4968.

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عنوان ژورنال:
  • Journal of the American Chemical Society

دوره 129 45  شماره 

صفحات  -

تاریخ انتشار 2007