Structure–property relationships for solubility of monosaccharides

A series of difficulties make inaccessible precise experimental determinations of solubilities in standard conditions for monosaccharides; in water, the monosaccharides may switch from the acyclic to cyclic form and also the cyclic forms can undergo mutarotation. There are many ways to express the structural information as structure descriptors, but the alternatives become fewer when looking for invariants with good identification abilities, and the characteristic polynomial is one of them. The disadvantage of the characteristic polynomial resides in the fact that is defined with disregard of the chemical information coming from the type of the element and the type of the bond. Here, an extension of the characteristic polynomial was used accounting for the chemical information. In water, monosaccharides exist in all forms, but only one is an invariant for all the acyclic form. If it is something in structure which associates the structure information with the solubility, then it is present in all its form including the acyclic one, and therefore, the acyclic forms can be used to derive structure–property relationships. A search for linear relationships expressing the solubility as a function of the structure of the acyclic forms of monosaccharides was conducted by using the extension of the characteristic polynomial. The search used the experimental data available to select the models that are able to estimate the solubility, with each different to the other in terms of the effects considered. Considering the obtained results, the extended characteristic polynomial provides a very good estimation capability for the solubilities of monosaccharides.