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(27) Conserved are the hydrophobic interactions with the piperidinering of Trp90, hydrogen bonds between C16=O and Tyr113−OH andbetween C1=O and Ile87−NH, a dipolar contact between C1 andTyr113−OH, as well as aromatic hydrogen bonds with Tyr57, Phe67,
Phe130, and C17=O.
(28) Kozany, C.; März, A.; Kress, C.; Hausch, F. Fluorescent probes tocharacterise FK506-binding proteins. ChemBioChem 2009, 10, 1402−1410.
(29) For the [4.3.1]bicycle, an additional conformation with an O1−C1−C2−N7 dihedral angle of 144° is possible. Modelling studiessuggested that this endoconformation is less stable by 2.5 kcal/molcompared to the exoform due to repulsions between C4 of the piperidinering and C9 of the linker (Figure 5d).
(30) Ismail, M. A.; Brun, R.; Easterbrook, J. D.; Tanious, F. A.; Wilson,W. D.; Boykin, D. W.Synthesis and antiprotozoal activity of azaanaloguesof furamidine. J. Med. Chem. 2003, 46, 4761−4769.