𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Methylation of zebularine investigated using density functional theory calculations

✍ Scribed by Lalitha Selvam; Fang Fang Chen; Feng Wang

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
540 KB
Volume
32
Category
Article
ISSN
0192-8651

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Deoxyribonucleic acid (DNA) methylation is an epigenetic phenomenon, which adds methyl groups into DNA. This study reveals methylation of a nucleoside antibiotic drug 1‐(β‐D‐ribofuranosyl)‐2‐pyrimidinone (zebularine or zeb) with respect to its methylated analog, 1‐(β‐D‐ribofuranosyl)‐5‐methyl‐2‐pyrimidinone (d5) using density functional theory calculations in valence electronic space. Very similar infrared spectra suggest that zeb and d5 do not differ by types of the chemical bonds, but distinctly different Raman spectra of the nucleoside pair reveal that the impact caused by methylation of zeb can be significant. Further valence orbital‐based information details on valence electronic structural changes caused by methylation of zebularine. Frontier orbitals in momentum space and position space of the molecules respond differently to methylation. Based on the additional methyl electron density concentration in d5, orbitals affected by the methyl moiety are classified into primary and secondary contributors. Primary methyl contributions include MO8 (57a), MO18 (47a), and MO37 (28a) of d5, which concentrates on methyl and the base moieties, suggest certain connection to their Frontier orbitals. The primary and secondary methyl affected orbitals provide useful information on chemical bonding mechanism of the methylation in zebularine. © 2011 Wiley Periodicals, Inc. J Comput Chem, 2011

📜 SIMILAR VOLUMES

The calculation of magnetisabilities usi
The calculation of magnetisabilities using current density functional theory
✍ Aaron M. Lee; Susan M. Colwell; Nicholas C. Handy 📂 Article 📅 1994 🏛 Elsevier Science 🌐 English ⚖ 680 KB

The theory for the calculation of magnetisabilities using current density functional theory, which follows from the original theory of Vignale, Rasolt and Geldart, has been implemented. We present an initial application of this theory to the set of small molecules HZ, HF, Nz. CO, H20, and NH3.

Theoretical auger electron spectra of po
Theoretical auger electron spectra of polymers by density functional theory calculations using model dimers
✍ Takao Otsuka; Seiji Koizumi; Kazunaka Endo; Hiroyuki Kawabe; Delano P. Chong 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 155 KB

## Abstract We propose a new approach for analysis of Auger electron spectra (AES) of polymers by density functional theory (DFT) calculations with the Slater's transition‐state concept. Simulated AES and X‐ray photoelectron spectra (XPS) of four polymers [(CH~2~CH~2~)~__n__~ (PE), (CH~2~CH(CH~3~))

Conformational analysis of n-alkanes usi
Conformational analysis of n-alkanes using density functional theory. Comparison with ab initio calculations
✍ Seiji Tsuzuki; Tadafumi Uchimaru; Kazutoshi Tanabe 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 269 KB

Relative conformational energies of n-butane, n-pentane and n-hexane were calculated by the DFT method (Becke's exchange and Lee, Yang and Parr's correlation functionals) with the 6-31G \* basis set. The calculated energies were compared with experimental values and ab initio calculations. The DFr r