N-Glycosylamines of 4,6-O-ethylidene-α-D-glucopyranose: synthesis, characterisation and structure of CO2H, Cl and F ortho-substituted phenyl derivatives and metal ion complexes of the CO2H derivative

Abstract

A saccharide based ligand suitable for metal binding (HL_COOH) has been synthesized using 4,6-O-ethylidene-α-D-glucopyranose (4,6-O-EGP) and anthranilic acid. A few analogous glycosylamines with chloro and fluoro ortho substitutions have also been synthesized and characterised. Complexes of HL_COOH with Na⁺, K⁺, Mg²⁺, Ca²⁺, Ba²⁺, Cd²⁺ and Hg²⁺ have been isolated and characterised fully. The crystal structures of 4,6-O-EGP, the chloro analogue of HL_COOH and the K⁺ complex of L_COOH are established. The anomeric nature, orientation of the binding core and the co-ordination aspects of K⁺ have been derived from these structures.