Artículos de revistas
Stereoelectronic Effects Of The Glycosidic Linkage On The Conformational Preference Of D-sucrose
Registro en:
Rsc Advances. Royal Soc Chemistry, v. 6, p. 112806 - 112812, 2016.
2046-2069
WOS:000389905300012
10.1039/c6ra24413k
Autor
Rozada
Thiago de Castro; Pontes
Rodrigo Meneghetti; Rittner
Roberto; Basso
Ernani Abicht
Institución
Resumen
Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) The stereoelectronic effects involved in the conformations shown by D-sucrose were analysed at the M06-2X/6-31++ G(d, p) level, both under vacuum and in water with the continuum solvation model IEF-PCM, and employing the natural bond orbital theory (NBO) and non-covalent interactions (NCI). Different groups of conformations for D-sucrose in relation to the glycosidic linkage were evaluated and the results showed that not only were hydrogen bonds important to explain the relative energy observed, but it was also necessary to consider any stabilizing orbital interactions involving the glycosidic linkage. The most stable conformation observed in water had dihedral angles for the glycosidic linkage with values of 110.8 degrees and -44.9 degrees for phi and psi, respectively. 6 114 112806 112812 Brazilian Council for Scientific and Technological Development (CNPq) FAPESP [2014/25903-6] Fundacao Araucaria [211-14-20133971] Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)