How the configurational changes influence on molecular characteristics. The alkyl 3-azido-2,3-dideoxy-D-hexopyranosides - Theoretical approach

Abstract

In this paper we present two currents of our research. The first goal was the geometry optimization of the structures of derivatives of the alkyl 3-azido-2,3-dideoxy-D-hexopyranosides. Then, we examine the influence of the applied quantum methods on the values of molecular features describing these structures. We use two methods for geometry optimization: the semi-empirical PM7 method and DFT B3LYP/6-31++G* method. The results of comparison parameters of descriptors indicate that there are no statistical differences obtained from both methods. Thus, we recommend the PM7 method for geometry optimization of the derivatives of the alkyl 3-azido-2,3-dideoxy-D-hexopyranosides due to its time and computer resources requirements. Another part of the research was the examination, which groups of descriptors are the most suitable for identifying the similarities in the configuration, the substituents pattern and the molecular mass of 232 examined structures. To explore relation between configuration changes of the 3-azidosaccharides and influence of these changes on the molecular characteristic, we use hierarchical cluster analysis (HCA), where WHIM, 3D-MORSE, RDF and GETAWAY descriptors were selected. Depending on the group of descriptors, molecules are divided in various ways. In general, saccharide' structures are divided into groups based on the configuration of substituents (combination of epimers) or length of the O-glycoside chain. Never before, these saccharides derivatives, were investigated by chemometric analysis. The most problematic issue in experimental and theoretical research is the configuration of substituents in pyranoside ring. Due to vast number of configurations, it is possible to obtain massive amount of diverse structures. This problem concerns us and opens opportunity in investigation the effect of configuration on the parameter of molecules.

Keywords: 3-Azidodeoxysaccharides; Chemometric analysis; DFT B3LYP/ 6–31++G*; HCA analysis; Molecular descriptors; PM7.