The Development of Novel Antibiotics Using ... - Jacobs University

The polar carbamate group participates efficiently in strengthening the binding interactions in the
formed complex 42. In addition to improving water solubility, introducing polar functionalities
and isolation of the macrocycle, which binds preferentially to oligopeptides can lead to discovery
of a novel macrocycle which can function as an antibiotic. We probed the dynamic reversibility
of tetra-carbohydrazide cyclophanes and proved that they were fully reversible under thermo-
dynamic control. We hope that this new class of macrocycles will find wide applications in drug
discovery using DCC.
Table 4. High resolution ESI-TOF MS data in the positive ion mode for library members hosting oligopeptides,
products appeared as [M+H] + ions
Host/Guest
complex
Measured m/z Molecular Formula Theoretical m/z Error
[ppm]
28/37 1489.6005 [M+H] + C 69 H 84 N 16 O 22 1489.6019 0.9
30/37 1423.5649 [M+H] + C 68 H 78 N 16 O 19 1423.5702 3.7
32/37 1564.6445 [M+H] + C 75 H 89 N 17 O 21 1564.6492 3.0
33/37 1348.5243 [M+H] + C 62 H 73 N 15 O 20 1348.5229 ˗1.0
28/38 1418.5591 [M+H] + C 66 H 79 N 15 O 21 1418.5648 4.0
30/38 1352.5285 [M+H] + C 65 H 73 N 15 O 18 1352.5331 3.4
32/38 1493.6091 [M+H] + C 72 H 84 N 16 O 20 1493.6121 2.0
40 1223.4929 [M+H] + C 60 H 66 N 14 O 15 1223.4905 ˗2.0
41 1289.5235 [M+H] + C 61 H 72 N 14 O 18 1289.5222 ˗1.0
42 1364.5635 [M+H] + C 67 H 77 N 15 O 17 1364.5695 4.4
43 1162.6380 [M+H] + C 48 H 87 N 15 O 18 1162.6426 4.0
44 1549.8487 [M+H] + C 64 H 116 N 20 O 24 1549.8544 3.7
Acknowledgements
Hany Nour deeply thanks Deutscher Akademischer Austauschdienst (DAAD) for financial
support and Jacobs University for excellent facilities.
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