Stereoselective noncovalent interactions of monosaccharides with hydrazine

Proton-bound complexes between underivatized monosaccharides and hydrazine have been generated in an ion trap mass spectrometer by electrospray ionization (ESI) and their collision induced decomposition (CID) investigated. The CID spectra of the selected complexes are invariably characterized by losses of hydrazine and several water molecules in proportions and at collision energies which markedly depend upon the nature and the structural features of the specific monosaccharide. Structural analysis of the proton-bound monosaccharide/hydrazine complexes at the B3LYP/6-31G(d,p) level of theory allowed to interpret the mass spectrometric results in terms of the specific intracomplex interactions between the amine and the various functional groups of the monosaccharide.