DFT/B3LYP Study of Thermochemistry of D-Glucosamine, a Representative Polyfunctional Bioorganic Compound


Department of Chemistry,Sharif University of Technology


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
Anity (MIA), metal binding sites, Anion Anity (AA), acidity and proton anity, have been
explored, using the Density Functional Theory (DFT) and a 6-311++Gbasis 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 di erent 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.