The crystal and molecular structures of esculetin 6-glucoside and 7-glucoside.

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概要

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• The structures of two dihydroxycoumarin glucosides, esculetin 6-glucoside (<B>E6G</B>) and escultin 7-glucoside (<B>E7G</B>) have been determined by the X-ray analysis. The crystal data are: <B>E6G</B>, C<SUB>15</SUB>H<SUB>16</SUB>O<SUB>9</SUB>·1.5H<SUB>2</SUB>O, orthorhombic P2<SUB>1</SUB>2<SUB>1</SUB>2<SUB>1</SUB> with <I>a</I>=11.358(2), <I>b</I>=36.850(9), <I>c</I>=7.663(1) Å and <I>Z</I>=8: and <B>E7G</B>, C<SUB>15</SUB>H<SUB>16</SUB>O<SUB>9</SUB>·2H<SUB>2</SUB>O, orthorhombic P2<SUB>1</SUB>2<SUB>1</SUB>2<SUB>1</SUB> with <I>a</I>=4.507(1), <I>b</I>=13.077(3), <I>c</I>=27.748(5) Å and <I>Z</I>=4. Both structures were solved by the direct method and refined by the least-squares to the final <I>R</I> values of 0.073 (2036 reflections) for <B>E6G</B> and 0.069 (1037 reflections) for <B>E7G</B>. The geometries of the glucosyl linkages in <B>E6G</B> and <B>E7G</B> are different: the torsion angles around the glucosidic C–O bond are −58.2° and 14.3° for the two crystallographically independent <B>E6G</B> molecules and 9.9° for <B>E7G</B>. The glucosidation at the 6-hydroxyl group causes little effect on the conjugation of the coumarin moiety, whereas the conjugation is greatly decreased in the glucosidation at 7-hydroxyl group. This fact suggests that <B>E6G</B> is energetically more stable than <B>E7G</B>. The enzymatic transglucosidation from 7- to 6-hydroxyl group may proceed utilizing such an energy difference.

• 公益社団法人 日本化学会の論文

著者

• SHIRAKI Masaru

  Research Institute for Polymers and Textiles

• Saito Norio

  Chemical Laboratory Meiji-gakuin University

• Sato Mitsuhiko

  Department Of Biology Faculty Of Science Tokyo Metropolitan University

• Ueno Katsuhiko

  Research Institute for Polymers and Textiles

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