Conformational search and spectroscopic analysis of bis -β- d -glucopyranosyl azacrown derivative
| Autor: | Stanislaw Porwanski, Marta Adamiak, Anna Ignaczak |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Hydrogen bond Chemistry Chemical shift Organic Chemistry Infrared spectroscopy 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry 0104 chemical sciences NMR spectra database Crystallography chemistry.chemical_compound Drug Discovery Molecule Conformational isomerism Derivative (chemistry) |
| Zdroj: | Tetrahedron. 74:2166-2173 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.03.025 |
| Popis: | 1,10-N,N′-bis-(β- d -ureidoglucopyranosyl)-4,7,13-trioxa-1,10-diazacyclopentadecane is a new, recently synthesized compound, which exhibits complexation ability towards drugs. In the present study various theoretical methods, including molecular mechanics, computer simulations, semiempirical and DFT calculations, are applied to find the lowest energy conformers of this molecule in vacuo and in aqueous solution. For the most stable structures the vibrational frequencies as well as the C and H chemical shifts were computed. Along with the theoretical investigation the IR in the KBr discs and the NMR spectra in water and in pyridine were experimentally recorded. It is shown that in the lowest energy structures the two glucosyl units are placed on the same side of the diazacrown ring with their mutual orientations favoring formation of hydrogen bonds. The “open” structure, in which no such hydrogen bonds can be formed, is found to have much higher energy. The computed and measured IR spectra and NMR chemical shifts are compared and discussed in detail. The most stable structures are analyzed with respect to the possible mechanism of complexation of drugs. |
| Databáze: | OpenAIRE |
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