Crystal structure of adenine-1-(2-carboxyethyl)uracil (1:1) complex. A model for interactions of amino acid side chains with nucleic acid base pair.

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概要

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• As a model for protein-nucleic acid interactions, crystals of the title complex were prepared from a water–ethanol (1 : 1) solution containing equimolar amounts of adenine and 1-(2-carboxyethyl)uracil. The space group is P2<SUB>1</SUB>/c with the unit cell dimensions of <I>a</I>=12.567(1), <I>b</I>=13.358(1), <I>c</I>=8.032(1) Å and β=93.28(1)°. The crystal structure was determined by X-ray analysis. The final <I>R</I> value was 0.053. The adenine and uracil moieties form a reversed Hoogsteen base pair in which N(7) and N(6) of adenine are hydrogen-bonded with N(3) and O(2) of uracil, respectively. The carboxyl group is dissociated and hydrogen-bonded to the protonated N(1) of adenine in the adjacent base pair at a distance of 2.542(3) Å. It is suggested that the protonation of adenine–uracil reversed Hoogsteen base pair could occur to make the base pair more stable, and the dissociated carboxyl group may be hydrogen-bonded to it in the protein–nucleic acid interactions.

• 公益社団法人 日本化学会の論文

著者

• Takenaka Akio

  Laboratory of Chemistry for Natural Products, Tokyo Institute of Technology

• Sasada Yoshio

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Fujita Shigeo

  Laboratory of Chemistry for Natural Products, Tokyo Institute of Technology

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