Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues

Hernández-Hernández, Luis Alberto; Yi, Ruiqin; Cleaves, Henderson James; Fuentes-Cabrera, Miguel; Sumpter, Bobby G.; Hernández-Hernández, Arturo; Rangel, Eduardo; Vallejo, Emmanuel

doi:10.1002/qua.25714

Title: Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues

Journal Article · Sun Sep 02 00:00:00 EDT 2018 · International Journal of Quantum Chemistry

DOI:https://doi.org/10.1002/qua.25714· OSTI ID:1474511

Hernández-Hernández, Luis Alberto ^[1]; Yi, Ruiqin ^[2]; Cleaves, Henderson James ^[3]; Fuentes-Cabrera, Miguel ^[4]; Sumpter, Bobby G. ^[4]; Hernández-Hernández, Arturo ^[1];

^[1]; Vallejo, Emmanuel ^[1]

Univ. Autonoma del Estado de Hidalgo, Pachuca (Mexico)
Tokyo Inst. of Technology (Japan)
Tokyo Inst. of Technology (Japan); Inst. for Advanced Study, Princeton, NJ (United States); Blue Marble Space Inst. of Science, Washington, DC (United States); Georgia Inst. of Technology, Atlanta, GA (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

A theoretical and experimental characterization of N(1)-(2',3'-dihydroxypropil)thymine (DHPT), a potential prebiotic nucleoside analogue of 5-methyluridine, is performed. A proposed methodology based on a solvation method was used to study conformational transformations of the different low-energy conformers of DHPT according to time-dependent IR spectroscopy. NMR and CD spectroscopy provides additional evidence of these transformations. The conformational transformations appear to be due to solvent and DHPT interactions. This highlights the importance of experimental conditions on conformer ratio equilibrium, in particular, the interpretation of experimental conditions used for determining the stereoisomers' absolute configuration.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Oak Ridge Leadership Computing Facility (OLCF)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC05-00OR22725; DE‐AC05‐00OR22725

OSTI ID:: 1474511

Alternate ID(s):: OSTI ID: 1468362; OSTI ID: 1474684

Journal Information:: International Journal of Quantum Chemistry, Vol. 118, Issue 20; ISSN 0020-7608

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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