TY - JOUR
T1 - Conformational preference and chiroptical response of carbohydrates D-ribose and 2-deoxy-D-ribose in aqueous and solid phases
AU - Quesada-Moreno, Maria Mar
AU - Azofra Mesa, Luis Miguel
AU - Aviles-Moreno, Juan Ramon
AU - Alkorta, Ibon
AU - Elguero, Jose
AU - Lopez-Gonzalez, Juan Jesus
PY - 2013
Y1 - 2013
N2 - 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.
AB - 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.
UR - http://pubs.acs.org.ezproxy.lib.monash.edu.au/doi/pdf/10.1021/jp405121s
U2 - 10.1021/jp405121s
DO - 10.1021/jp405121s
M3 - Article
VL - 117
SP - 14599
EP - 14614
JO - Journal of Physical Chemistry B
JF - Journal of Physical Chemistry B
SN - 1520-6106
IS - 47
ER -