D-glucosamine, as a representative polyfunctional compound, is a bioactive amino sugar In this study, the gas phase thermochemical properties of D-glucosamine, including its Metal Ion Affinity (MIA), metal binding sites, Anion Affinity (AA), acidity and proton affinity, have been explored, using the Density Functional Theory (DFT) and a 6-311++G**basis set. The summary of the MIA and AA results (in kcal/mol-1) are: Li+= 67.6, Na+= 51.1, K+= 37.3, Mg2+= 207.9, Ca2+= 150.4, Zn2+= 251.2, Cl-= 27.4, CN-= 28.0. The acidity values calculated at different sites, including four -OH groups and one -NH2 group, range from 344.0 to 373.0 kcal/mol-1. These results, surprisingly, indicate how drastically the presence of multiple -OH and -NH2 groups may vary the thermochemical properties of a polyfunctional bioorganic compound, such as D-glucosamine.