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

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.
Authors:
 [1] ;  [2] ;  [3] ;  [4] ;  [4] ;  [1] ; ORCiD logo [1] ;  [1]
  1. Univ. Autonoma del Estado de Hidalgo, Pachuca (Mexico)
  2. Tokyo Inst. of Technology (Japan)
  3. 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)
  4. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Grant/Contract Number:
AC05-00OR22725
Type:
Accepted Manuscript
Journal Name:
International Journal of Quantum Chemistry
Additional Journal Information:
Journal Name: International Journal of Quantum Chemistry; Journal ID: ISSN 0020-7608
Publisher:
Wiley
Research Org:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1474511
Alternate Identifier(s):
OSTI ID: 1468362; OSTI ID: 1474684

Hernández-Hernández, Luis Alberto, Yi, Ruiqin, Cleaves, Henderson James, Fuentes-Cabrera, Miguel, Sumpter, Bobby G., Hernández-Hernández, Arturo, Rangel, Eduardo, and Vallejo, Emmanuel. Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues. United States: N. p., Web. doi:10.1002/qua.25714.
Hernández-Hernández, Luis Alberto, Yi, Ruiqin, Cleaves, Henderson James, Fuentes-Cabrera, Miguel, Sumpter, Bobby G., Hernández-Hernández, Arturo, Rangel, Eduardo, & Vallejo, Emmanuel. Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues. United States. doi:10.1002/qua.25714.
Hernández-Hernández, Luis Alberto, Yi, Ruiqin, Cleaves, Henderson James, Fuentes-Cabrera, Miguel, Sumpter, Bobby G., Hernández-Hernández, Arturo, Rangel, Eduardo, and Vallejo, Emmanuel. 2018. "Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues". United States. doi:10.1002/qua.25714.
@article{osti_1474511,
title = {Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues},
author = {Hernández-Hernández, Luis Alberto and Yi, Ruiqin and Cleaves, Henderson James and Fuentes-Cabrera, Miguel and Sumpter, Bobby G. and Hernández-Hernández, Arturo and Rangel, Eduardo and Vallejo, Emmanuel},
abstractNote = {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.},
doi = {10.1002/qua.25714},
journal = {International Journal of Quantum Chemistry},
number = ,
volume = ,
place = {United States},
year = {2018},
month = {9}
}

Works referenced in this record:

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Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
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