Abstract
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.
| Original language | English |
|---|---|
| Article number | e25714 |
| Journal | International Journal of Quantum Chemistry |
| Volume | 118 |
| Issue number | 20 |
| DOIs | |
| State | Published - Oct 15 2018 |
Funding
M. Fuentes-Cabrera and B. G. Sumpter acknowledge work performed at the Center for Nanophase Materials Sciences (CNMS), a US Department of Energy (DOE) Office of Science User Facility. Yi Ruiqin and H. J. Cleaves II acknowledge support from the JSPS KAKENHI Grant-in-Aid for Scientific Research on Innovative Areas “Hadean Bioscience”, grant number JP26106003. This project was also partially supported by the ELSI Origins Network (EON), which is supported by a grant from the John Templeton Foundation. The opinions expressed in this publication are those of the authors and do not necessarily reflect the views of the John Templeton Foundation. They would also like to thank Dr. Yayoi Hongo (ELSI) for assistance obtaining MS spectra and Dr. Gary Newman and Professor Nicholas Hud (Georgia Institute of Technology) for assistance obtaining CD spectra. This research was conducted at the Escuela Superior de Apan and the CNMS. Computations also used resources of the Oak Ridge Leadership Computing Facility at the Oak Ridge National Laboratory, which is supported by the Office of Science of the U.S. DOE under Contract No. DE-AC05-00OR22725. We acknowledge computational facilities to ABACUS and Cluster Abacus-I. L. A. Hernández-Hernández and A. Hernández-Hernández acknowledge technical support of A. Garcia-Sotelo and M. Guerrero from Cinvestav-IPN. We acknowledge computational and experimental facilities to Dr. Miguel A. Melendez Lira from Cinvestav-IPN. The authors acknowledge to J. Jesús Pelayo for the fruitful comments on this work. Japan Society for the Promotion of Science KAKENHI Grant-in-Aid for Scientific Research on Innovative Areas “Hadean Bioscience”, Grant/Award Number: JP26106003; U.S. Department of Energy, Grant/Award Number: DE-AC05-00OR22725; Office of Science; Oak Ridge National Laboratory; Georgia Institute of Technology; John Templeton Foundation information Japan Society for the Promotion of Science KAKENHI Grant-in-Aid for Scientific Research on Innovative Areas ?Hadean Bioscience?, Grant/Award Number: JP26106003; U.S. Department of Energy, Grant/Award Number: DE-AC05-00OR22725; Office of Science; Oak Ridge National Laboratory; Georgia Institute of Technology; John Templeton FoundationM. Fuentes-Cabrera and B. G. Sumpter acknowledge work performed at the Center for Nanophase Materials Sciences (CNMS), a US Department of Energy (DOE) Office of Science User Facility. Yi Ruiqin and H. J. Cleaves II acknowledge support from the JSPS KAKENHI Grant-in-Aid for Scientific Research on Innovative Areas ?Hadean Bioscience?, grant number JP26106003. This project was also partially supported by the ELSI Origins Network (EON), which is supported by a grant from the John Templeton Foundation. The opinions expressed in this publication are those of the authors and do not necessarily reflect the views of the John Templeton Foundation. They would also like to thank Dr. Yayoi Hongo (ELSI) for assistance obtaining MS spectra and Dr. Gary Newman and Professor Nicholas Hud (Georgia Institute of Technology) for assistance obtaining CD spectra. This research was conducted at the Escuela Superior de Apan and the CNMS. Computations also used resources of the Oak Ridge Leadership Computing Facility at the Oak Ridge National Laboratory, which is supported by the Office of Science of the U.S. DOE under Contract No. DE-AC05-00OR22725. We acknowledge computational facilities to ABACUS and Cluster Abacus-I. L. A. Hern?ndez-Hern?ndez and A. Hern?ndez-Hern?ndez acknowledge technical support of A. Garcia-Sotelo and M. Guerrero from Cinvestav-IPN. We acknowledge computational and experimental facilities to Dr. Miguel A. Melendez Lira from Cinvestav-IPN. The authors acknowledge to J. Jes?s Pelayo for the fruitful comments on this work.
| Funders | Funder number |
|---|---|
| CNMS | |
| Center for Nanophase Materials Sciences | |
| ELSI Origins Network | |
| EON | |
| John Templeton FoundationM | |
| US Department of Energy | |
| U.S. Department of Energy | DE-AC05-00OR22725 |
| U.S. Department of Energy | |
| John Templeton Foundation | |
| Office of Science | |
| Oak Ridge National Laboratory | |
| Georgia Institute of Technology | |
| Japan Society for the Promotion of Science | JP26106003 |
| Japan Society for the Promotion of Science |
Keywords
- conformational transformations
- nucleoside analogues
- stereoisomers