Conformational preference and chiroptical response of carbohydrates D-ribose and 2-deoxy-D-ribose in aqueous and solid phases

Maria Mar Quesada-Moreno, Luis Miguel Azofra Mesa, Juan Ramon Aviles-Moreno, Ibon Alkorta, Jose Elguero, Juan Jesus Lopez-Gonzalez

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15 Citations (Scopus)


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, a-furanose, ?-furanose, a-pyranose, and ?-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 a- and ?-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.
Original languageEnglish
Pages (from-to)14599 - 14614
Number of pages16
JournalJournal of Physical Chemistry B
Issue number47
Publication statusPublished - 2013
Externally publishedYes

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