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Computer‐Aided Molecular Design of Hydrogen Bond Equivalents of Nucleobases: Theoretical Study of Substituent Effects on the Hydrogen Bond Energies of Nucleobase Pairs
Author(s) -
Kawahara Shunichi,
Uchimaru Tadafumi
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300015
Subject(s) - chemistry , substituent , nucleobase , hydrogen bond , ab initio , computational chemistry , nucleic acid , bond energy , molecular orbital , ab initio quantum chemistry methods , bond order , low barrier hydrogen bond , base pair , bond length , crystallography , stereochemistry , molecule , organic chemistry , dna , biochemistry
Substituent effects on the hydrogen bond energies of Watson−Crick‐type base pairs, formed between a chemically modified nucleic acid base derivative and an unmodified one, were evaluated by ab initio molecular orbital theory. Different trends were observed in the relationship between the substituent and the hydrogen bond energy in each base pair. The predicted hydrogen bond energies correlated well with the experimentally measured binding properties, and so ab initio calculation appears to be an effective method with which to estimate the stabilities of base pairs between chemically modified nucleic acid bases. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)