A polyoxapolyaza macrobicyclic receptor for the recognition of zwitterions

Pedro Mateus; Rita Delgado; Paula Brandão; Vítor Félix

doi:10.1039/C2OB25725D

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Organic & Biomolecular Chemistry

Issue 29, 2012

The international home of synthetic, physical and biomolecular organic chemistry.

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A polyoxapolyaza macrobicyclic receptor for the recognition of zwitterions

Pedro Mateus,^a Rita Delgado,*^a Paula Brandão^b and Vítor Félix^c

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Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal
E-mail: delgado@itqb.unl.pt ;
Tel: (+351) 214469737

Departamento de Química, CICECO, Universidade de Aveiro, 3810-193 Aveiro, Portugal

Departamento de Química, CICECO, and Secção Autónoma de Ciências da Saúde, Universidade de Aveiro, 3810-193 Aveiro, Portugal

Org. Biomol. Chem., 2012,10, 5529-5532

DOI: 10.1039/C2OB25725D
Received 13 Apr 2012, Accepted 19 Jun 2012
First published online 20 Jun 2012

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Abstract
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A polyoxapolyaza heteroditopic macrobicyclic compound (btpN₄O₃) was synthesized. The acid–base behaviour of the compound as well as its binding ability for zwitterionic amino acids were studied by potentiometry at 298.2 ± 0.1 K in H₂O–MeOH (50:50 v/v) and at I = 0.10 ± 0.01 M in NMe₄TsO. The H_nbtpN₄O₃ⁿ⁺ showed preference for amino acids containing tetrahedral anionic groups.