Journal of the Chemical Society, Dalton Transactions p. 3107 - 3112 (1994)
Update date:2022-08-03
Topics:
Bayada, Anne
Lawrance, Geoffrey A.
Maeder, Marcel
O'Leary, Margaret A.
Copper(II)-directed condensation between 4,7-diazadecane-1,10-diamine, formaldehyde and 1-nitro-3-(2-nitroethyl)benzene yielded the macrocyclic <10-nitro-10-(3-nitrobenzyl)-1,4,8,12-tetraazacyclopentadecane>copper(II) ion.Reduction (Zn,HCl) gave the pendant-arm macrocycle 10-(3-aminobenzyl)-1,4,8,12-tetraazacyclopentadec-10-ylamine as the hydrochloride salt.Condensation reactions with 1-nitro-4-(2-nitroethyl)benzene and 2-phenylnitroethane were also successful.The capacity of the aminobenzyl C-pendant introduced by this facile chemistry for covalent attachment has been examined by attachment of 10-(3-aminobenzyl)-1,4,8,12-tetraazacyclopentadec-10-ylamine to the acidic cation-exchange resin CM Bio-Gel A and to horse heart cytochrome c, employing a water-soluble carbodiimide coupling agent at pH 5 to promote amide formation.The attachment was probed by copper(II) complexation to the bound macrocycle and subsequent spectroscopic or voltammetric analysis.
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