Acta Chim. Sinica ›› 2015, Vol. 73 ›› Issue (4): 357-365.DOI: 10.6023/A14120869 Previous Articles    

Article

核酸碱基与甘氨酸二肽间氢键作用的最佳位点

刘畅, 于歌, 黄翠英, 王长生   

  1. 辽宁师范大学化学化工学院 大连 116029
  • 投稿日期:2014-12-16 发布日期:2015-01-28
  • 通讯作者: 王长生 E-mail:chwangcs@lnnu.edu.cn
  • 基金资助:

    项目受国家自然科学基金(No. 21173109), 辽宁省优秀人才基金(No. LR2012037)和大连市领军人才资助.

Site Preferences of Nucleic Acid Bases Hydrogen Bonding to Glycine Dipeptide

Liu Chang, Yu Ge, Huang Cuiying, Wang Changsheng   

  1. School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029
  • Received:2014-12-16 Published:2015-01-28
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21173109), Program for Liaoning Excellent Talents in University, China (No. LR2012037), and Program for Leading Figures in Dalian, China.

The optimal structures of twenty-eight hydrogen-bonded complexes, containing one glycine dipeptide molecule and one of the nucleic acid base adenine, thymine, uracil, guanine and cytosine, were obtained at the B3LYP/6-31+G(d,p) level. The binding energies of these complexes were further evaluated at the CP-corrected MP2/aug-cc-pVTZ level. The site-preferences of the five nucleic acid bases hydrogen bonding to glycine dipeptide are explored. The calculation results show that any of the five nucleic acid bases can hydrogen bond to glycine dipeptide through different binding site. The hydrogen-bonded complexes formed through site A3 of adenine, site T1 of thymine, site U1 of uracil, site C1 of cytosine and site G3 of guanine are the most stable. The stability of the hydrogen-bonded complexes is associated with the enthalpy change of the protonation/deprotonation reaction of the nucleic acid bases. The more negative the enthalpy change of the protonation reaction or the smaller the enthalpy change of the deprotonation reaction, the more stable the hydrogen-bonded complexes.

Key words: glycine dipeptide, nucleic acid base, hydrogen-bonded complex, binding energy, protonation reaction, deprotonation reaction