Crystal and Molecular Structures of Carbon-Bridged Pyrimidine Cyclonucleosides. Substrate Analogs of Ribonuclease A

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概要

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• The crystal and molecular structures of carbon-bridged 6,5'-cyclo-5'-deoxy-4-thiouridine (6,5'-Cs^4U), 6,5'-cyclo-5'-deoxy-2', 3'-O-isopropylideneuridine (6,5'-CiU) and 6,6'-cyclo-5', 6'-dideoxy-allofuranosyluracil (6,6'-CU) have been determined by X-ray diffraction. The molecular conformations of 6,5'-Cs^4U and 6,5'-CiU are very similar; the conformation about the glycosidic bond is anti (low region), the torsion angle O(4')-C(1')-N(1)-C(2)being -150.0° for 6,5'-Cs^4U and -145.5° for 6,5'-CiU, and the sugar puckering being both O(4')-exo. On the other hand, 6,6'-CU takes the glycosidic torsion angle of -116.9(4)° (middle anti region) and the sugar conformation of C(4')-endo. The cyclization causes little alteration in the geometry of the base moiety. 6,5'-Cs^4U and 6,5'-CiU exhibit the similar base-base interactions between adjacent molecules, although their molecular packings are quite different; the 4-thiouracil or uracil moiety interacts with adjacent base moieties through hydrogen bonding and stacking interactions. In 6,6'-CU, cyclonucleosides were connected by hydrogen bondings between the hydroxyl and sugar ring oxygen atoms and between the hydroxyl groups and the base nitrogen and oxygen atoms. As the 2', 3'-cyclic phosphates of these carbon-bridged cyclonucleosides are hydrolyzed by ribonuclease A, it is suggested that the conformers found in these cyclonucleosides are recognized by the enzyme.

• 公益社団法人日本薬学会の論文
• 1989-08-25

著者

• 冨田 研一

  Faculty of Pharmaceutical Sciences, Osaka University

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 上田 亨

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 山縣 ゆり子

  Faculty of Pharmaceutical Sciences, Osaka University

• 佐野 友春

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 碓井 博幸

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 山縣 ゆり子

  阪大薬

• 山縣 ゆり子

  Faculty Of Pharmaceutical Sciences Osaka University

• 佐野 友春

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 上田 亨

  北海道大学薬学部

• 碓井 博幸

  Daiichi Pharmaceutical Co., Ltd.,

• 冨田 研一

  Faculty Of Pharmaceutical Sciences Osaka University

• 碓井 博幸

  Daiichi Pharmaceutical Co. Ltd.

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