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

Introduction
incorporate β-cyclodextrin units. 17 Terephthaldehyde 13 forms inclusion complexes with
β-cyclodextrin 14 in water. 18 β-Cyclodextrin 14 was reported to have a diameter of 7.8 Å, while
the cavity size of trianglimine 4 was reported to be 10.5 Å. 9,10,19 Trianglimine 4 and β-cyclodextrin
14 have accordingly complement in their sizes. The [3+3]-cyclocondensation reaction of
inclusion complex 15 with (1R,2R)-1,2-diaminocyclohexane 1 forms an interlocked catenanelike
intermediate structure, which upon in situ reduction with sodium borohydrides (NaBH 4 )
gives 16 (Figure 2.5).
Figure 2.5 Trianglimine 4 forming interlocked structure with β-cyclodextrin 14.
Trianglamines have been used as chiral probes for recognition of chiral carboxylic acids 17-22
both in the gas phase and in solution (Figure 2.6). 20-22 Molecular recognition in the gas phase was
investigated by ESI-MS and MS/MS by observing the molecular ion peaks corresponding to the
host/guest complexes (i.e., 23). Changes in CD-spectra (Circular dichroism) and titration NMR
confirm molecular recognition in solution.
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