Synthesis and binding properties of hybrid cyclophane-azamacrocyclic receptors

Benniston, A.C., Gunning, P. and Peacock, R.D. (2005) Synthesis and binding properties of hybrid cyclophane-azamacrocyclic receptors. Journal of Organic Chemistry, 70, pp. 115-123. (doi:10.1021/jo048621o)

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Abstract

Three new azamacrocyclic-cyclophane hybrid receptors L1, L2, and L3 have been synthesized that incorporate either 1,4,7,10-tetraazacyclododecane (cyclen) or 1,4,7-triazacyclononane (tacn) unit(s) tethered via a short amidic spacer to an electron donor and a H-bonding crown ether polycycle. The crown ether is designed to act as a host toward biologically relevant guests, whereas the macrocycle can coordinate a zinc(II) or a copper(II) ion. The pKa of this bound water in the zinc(II) complex of L1 and L2 is 7.5. Isothermal calorimetry experiments carried out on [ZnL1(OH2)](CF3SO3)2 and [Zn2L2(OH2)2](CF3SO3)4 in buffered water (pH 7.4) at 25 °C show that the host strongly binds a series of phosphate derivatives. In comparison, the complex [CuL3(OH2)2](CF3SO3)2 is a poor receptor toward phosphate substrates.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Peacock, Dr Robert
Authors: Benniston, A.C., Gunning, P., and Peacock, R.D.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry

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