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

Scope of Work
Terta-(hydrazinecarboxamide) cyclophanes (i.e., 13) possess flexible structures and unlike 10,
they cannot undergo dynamic exchange under normal condition, however in the presence of
Lewis-acid catalysts, they might undergo catalytic transamidation. 11 The novel tetra-(hydrazinecarboxamide)
cyclophanes 13 assume a conformation in which the NH moieties are syn-anti
oriented, which has been confirmed by 2D-ROESY NMR. A new class of two-armed receptors
(i.e., 14) was synthesized in extension to the synthetic strategy used in the preparation of the
novel macrocycles 10 and 13. 12 Receptor 14 showed unprecedented dual self-assembly and
recognition in the gas phase with formation of structurally unique associations of hosts and
guests. The NH moieties in 14 assume a syn-syn conformation, which is stabilized by inter- and
intramolecular hydrogen bonds. Selective recognition to chiral carboxylic acids and oligopeptide
guests has also been demonstrated.
Figure 3.6 Macrocycle 13 and receptor 14 which bind with oligopeptides.
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