N-Glycosylamines of 4,6-O-ethylidene-#alpha#-D-glucopyranose: synthesis, characterisation and structure of CO_2H, Cl and F ortho-substituted phenyl derivatives and metal ion complexes of the CO_2H derivative

摘要

A saccharide based ligand suitable for metal binding (HL_(COOH)) has been synthesized using 4,6-O-ethylidene-#alpha#-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~+, Mg~(2+), Ca~(2+), Ba~(2+), Cd~(2+) and Hg~(2+) 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.