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Title: Isomeric effects on the self-assembly of a plausible prebiotic nucleoside analogue: A theoretical study

Journal Article · · International Journal of Quantum Chemistry
DOI:https://doi.org/10.1002/qua.25314· OSTI ID:1341529
 [1];  [2];  [2];  [1]
  1. Escuela Superior de Apan, Universidad Autonoma del Estado de Hidalgo (Mexico)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science (CNMS) and Computer Science and Mathematics Division
+ Show Author Affiliations

For this study, the self-assembly properties of N(9)-(2,3-dihydroxypropyl adenine) (DHPA), a plausible prebiotic nucleoside analogue of adenosine, were investigated using density functional theory. Two different isomers were considered, and it is found that while both isomers can form a variety of structures, including chains, one of them is also able to form cages and helixes. When these results were put in the context of substrate supported molecular self-assembly, it is concluded that gas-phase self-assembly studies that consider isomer identity and composition not only can aid interpreting the experimental results, but also reveal structures that might be overlooked otherwise. In particular, this study suggest that a double-helical structure made of DHPA molecules which could have implications in prebiotic chemistry and nanotechnology, is stable even at room temperature. For example electrical properties (energy gap of 4.52eV) and a giant permanent electrical dipole moment (49.22 Debye) were found in our larger double-helical structure (3.7 nm) formed by 14 DHPA molecules. Lastly, the former properties could be convenient for construction of organic dielectric-based devices.

Research Organization:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Oak Ridge Leadership Computing Facility (OLCF)
Sponsoring Organization:
USDOE Office of Science (SC)
Grant/Contract Number:
AC05-00OR22725
OSTI ID:
1341529
Journal Information:
International Journal of Quantum Chemistry, Vol. 117, Issue 3; ISSN 0020-7608
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 2 works
Citation information provided by
Web of Science

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Cited By (2)

Theoretical and experimental evidence of conformational transformation in stereoisomers of nucleoside analogues
  • Hernández-Hernández, Luis Alberto; Yi, Ruiqin; Cleaves, Henderson James
  • International Journal of Quantum Chemistry, Vol. 118, Issue 20 https://doi.org/10.1002/qua.25714
journal September 2018
Computational study on the interaction of nucleobases with boron-rich boron nitride nanotubes journal July 2018

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
36 MATERIALS SCIENCE