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1H-nmr studies on the dinucleoside monophosphates containing 2′-halogeno-2′-deoxypurinenucleosides: Effects of 2′-substitutes on conformation

✍ Scribed by Seiichi Uesugi; Toshinori Kaneyasu; Junko Imura; Morio Ikehara; Doris M. Cheng; Lousing Kan; Paul O. P. Ts'o

Publisher
Wiley (John Wiley & Sons)
Year
1983
Tongue
English
Weight
694 KB
Volume
22
Category
Article
ISSN
0006-3525

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✦ Synopsis

Seven dinucleoside monophosphates containing 2'-halogeno-2'-deoxypurine nucleoside residue, dAfl-U, dAcl-U, dAbr-U, dAio-U, dGfl-U, dIfl-U, and dIfl-C, were chemically synthesized and investigated by '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 Csf-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 Cr-endo (3E) population and the base-base interaction in Nfl-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.

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