Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Polynucleotides. LV. Synthesis and Properties of Dinucleoside Monophosphates derived from Adenine 8, 2'-S- and Uracil 6, 2'-O-Cyclonucleosides. Further Support for the Left-Handed Stacking of Oligonucleotides having High-Anti Base Torsion Angles
池原 森男上杉 晴一志田 敏夫
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キーワード: paper chromatography
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1980 年 28 巻 1 号 p. 189-197

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Two sequence isomers of dinucleoside monophosphates, 8, 2'-anhydro-8-thio-9-β-D-arabinofuranosyladenylyl-(3'-5')-6, 2'-anhydro-6-oxy-1-β-D-arabinofuranosyluracil (AspU°) (III) and 6, 2'-anhydro-6-oxy-1-β-D-arabinofuranosyluridylyl-(3'-5')-8, 2'-anhydro-8-thio-9-β-D-arabinofuranosyladenine (U°pAs) (IV), were synthesized by condensation of suitably protected nucleoside and nucleotide units using dicyclohexyl carbodiimide as a condensing reagent. Examination of the UV, CD and NMR spectra of these dimers led us to the conclusion that, whereas compound III did not take a stacked conformation, compound IV took a well-stacked conformation, in which the bases were stacked along a left-handed screw axis. The adoption of this conformation could be interpreted in terms of the high base torsion angles in both nucleoside units.
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© The Pharmaceutical Society of Japan
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