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)

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