Conformational preferences of the flexible galactofuranose sugar in gas-phase

Oznur Yeni (1) , Abdul-Rahman Allouche (2) , Laurent Legentil (3) , Vincent Ferrières (3) , Isabelle Compagnon (1)

1 iLM - DYNAMO - iLM - Structure et dynamique multi-échelle des édifices moléculaires
2 iLM - THEOCHEM - iLM - Physico-chimie théorique
3 ISCR - Institut des Sciences Chimiques de Rennes

In contrast with the predominant pyranose form of galactose, galactofuranose is known to be highly flexible. Such flexibility poses a remarkable challenge in terms of structural studies, thus hindering the in depth understanding of the structure/function relationship in this rare sugar. A thorough computational study based on molecular dynamics and density functional theory supported by vibrational spectroscopy in the gas phase was carried out to provide a better understanding of the instrinsic conformational preferences of galactofuranose. Based on energetic and spectroscopic criteria, we report a subtantially reduced conformational landscape: methyl α-D-galactofuranose adopts E2/1E conformations and methyl β-D-galactofuranose adopts 1T2/1E conformations.

Mots clés: FURANOSE RING; SPECTROSCOPY; GLYCANS

Domaines: Chimie théorique et/ou physique

Oznur Yeni, Abdul-Rahman Allouche, Laurent Legentil, Vincent Ferrières, Isabelle Compagnon. Conformational preferences of the flexible galactofuranose sugar in gas-phase. Physical Chemistry Chemical Physics, 2023, 25 (30), pp.20373-20380. ⟨10.1039/d3cp01671d⟩. ⟨hal-04189817⟩