Interaction of metal ions with N-glycosylamines: isolation and characterization of the products of 4,6-O-benzylidene-N-(o-carboxyphenyl)-beta-D-glucopyranosylamine with different metal ions.
Metal-ion complexes of Li(+), Na(+), K(+), Mg(2+), Ca(2+), Ba(2+), Pb(2+), Cd(2+), Hg(2+) with 4,6-O-benzylidene-N-(o-carboxyphenyl)-beta-D-glucopyranosylamine were synthesized and isolated as solid products and characterized by analytical means as well as by spectral techniques, such as, 1H and 13C NMR, FTIR, absorption, FAB mass spectrometry, optical rotation and CD. While the alkali metal ions formed ML type of complexes, the other metal ions formed ML(2) type complexes. Molecular weights of the complexes of Li(+), Na(+) and K(+) were established based on the molecular-ion peaks in the FAB mass spectra. The saccharide portion remains in the beta-anomeric form even after the complexation. The spectral data, as well as the trends observed in the chemical shifts, indicate the interaction preferences between this glycosyl amine and different metal ions, and further reveal certain structural features of the complexes.
Das
T M
TM
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, 400 076, Mumbai, India.
Rao
C P
CP
Kolehmainen
E
E
D002104:Cadmium / Q000737:chemistry; D002942:Circular Dichroism; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006031:Glycosylation; D007477:Ions / Q000737:chemistry*; D007854:Lead / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D008628:Mercury / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D008673:Metals, Alkaline Earth / Q000737:chemistry*; D008956:Models, Chemical; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods
D007477:Ions; D008670:Metals; D008673:Metals, Alkaline Earth; D002104:Cadmium; D007854:Lead; C075822:glucopyranosylamine; D008628:Mercury; D005944:Glucosamine