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1 H‐nmr studies on the dinucleoside monophosphates containing 2′‐halogeno‐2′‐deoxypurinenucleosides: Effects of 2′‐substitutes on conformation
Author(s) -
Uesugi Seiichi,
Kaneyasu Toshinori,
Imura Junko,
Ikehara Morio,
Cheng Doris M.,
Kan Lousing,
Ts'o Paul O. P.
Publication year - 1983
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360220412
Subject(s) - chemistry , chemical shift , conformational isomerism , stereochemistry , furanose , substituent , population , nuclear magnetic resonance spectroscopy , base (topology) , alkane stereochemistry , electronegativity , crystallography , residue (chemistry) , proton , nucleoside , molecule , crystal structure , organic chemistry , ring (chemistry) , mathematical analysis , demography , mathematics , physics , quantum mechanics , sociology
Seven dinucleoside monophosphates containing 2′‐halogeno‐2′‐deoxypurine nucleoside residue, dAfl‐U, dAcl‐U, dAbr‐U, dAio‐U, dGfl‐U, and dIfl‐C, were chemically synthesized and investigated by 1 H‐nmr spectroscopy at 300 MHz. The sugar and backbone conformations of these compounds were analyzed by the spectral pattern of furanose proton resonances; and the extents of base‐base interaction were estimated from chemical shifts and their temperature‐dependent changes of base‐proton resonances. It is found that the population of C 3′ ‐ endo conformer and the extent of base‐base interaction decrease as the electronegativity of 2′‐substituent decreases in dAx‐U (x = fl, cl, br, and io) series. The C 3′ ‐ endo ( 3 E) population and the base‐base interaction in N fl‐U ( N = A,G)‐type dimers as well as dIfl‐C are relatively higher than the corresponding natural ribo‐dimers but can be recognized as grossly similar to the conformation of regular RNA dimers.