title: Conformational preference and chiroptical response of carbohydrates D-ribose and 2-deoxy-D-ribose in aqueous and solid phases.
abstract: This work targets the structural preferences of D-ribose and 2-deoxy-D-ribose in water solution and solid phase. A theoretical DFT (B3LYP and M06-2X) and MP2 study has been undertaken considering the five possible configurations (open-chain, α-furanose, β-furanose, α-pyranose, and β-pyranose) of these two carbohydrates with a comparison of the solvent treatment using only a continuum solvation model (PCM) and the PCM plus one explicit water molecule. In addition, experimental vibrational studies using both nonchiroptical (IR-Raman) and chiroptical (VCD) techniques have been carried out. The theoretical and experimental results show that α- and β-pyranose forms are the dominant configurations for both compounds. Moreover, it has been found that 2-deoxy-D-ribose presents a non-negligible percentage of open-chain forms in aqueous solution, while in solid phase this configuration is absent.
authors.affiliation: Department of Physical and Analytical Chemistry, University of Jaén , Campus Las Lagunillas, E-23071 Jaén, Spain.
authors.forename: María Mar
authors.initials: MM
authors.lastname: Quesada-Moreno
authors.forename: Luis Miguel
authors.initials: LM
authors.lastname: Azofra
authors.forename: Juan Ramón
authors.initials: JR
authors.lastname: Avilés-Moreno
authors.forename: Ibon
authors.initials: I
authors.lastname: Alkorta
authors.forename: José
authors.initials: J
authors.lastname: Elguero
authors.forename: Juan Jesús
authors.initials: JJ
authors.lastname: López-González
mesh_terms: D002236:Carbohydrate Conformation; D003855:Deoxyribose / Q000737:chemistry*; D008958:Models, Molecular; D012266:Ribose / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D014867:Water; D003855:Deoxyribose; D012266:Ribose