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Substituent effects of phthalimide‐based nucleoside analogs on binding a CG Watson–Crick base pair
Author(s) -
Xiao Z.,
Weisz K.
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1243
Subject(s) - chemistry , phthalimide , substituent , stereochemistry , guanosine , molecular structure of nucleic acids: a structure for deoxyribose nucleic acid , cytosine , nucleoside , residue (chemistry) , base pair , crystallography , dna , biochemistry
Five differently substituted phthalimide nucleosides were studied by NMR spectroscopic techniques for their ability to recognize and bind a cytosine–guanosine (CG) Watson–Crick base pair in CD 2 Cl 2 . Whereas only rather weak binding was observed for analogs with an amino, acetamido, or benzamido substituent, strong binding was observed with the analogs carrying an ureido and n ‐butyl ureido residue. 2D NOE measurements at low temperatures confirm the proposed binding mode for the high‐affinity ligands but indicate binding interactions for the weakly bound analogs different from the expected geometry. Copyright © 2007 John Wiley & Sons, Ltd.