Molecular Conformations of Carbon-Bridged Cyclodeoxyadenosines in the Solid State and in Solution.2'-Deoxy-8,2'-methanoadenosine and 2'-Deoxy-8,2'-ethanoadenosine

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• Two carbon-bridged cyclodeoxyadenosines, 2'-deoxy-8,2'-methanoadenosine (8,2'-MA) and 2'-deoxy-8.2'-ethanoadenosine (8,2'-EA), were investigated by X-ray and nuclear magnetic resonance (NMR) analyses. Both compounds crystallize in the orthorhombic system with space group P2_12_12_1. The unit-cell dimensions are a=9.427 (1), b=17.287 (2)and c=6.908 (1)Å for 8,2'-MA and a=15.599(4), b=19.468 (5) and c=9.955 (3) Å for 8,2'-EA. Both structures were solved by direct methods and refined to R values of 0.037 for 8,2'-MA and 0.052 for 8,2'-EA. There are two independent cyclonucleoside molecules and one isopropanol molecule per asymmetric unit in the crystal of 8,2'-EA. The glycosidec torsion angles, x, O(4')-C(1')-N(9)-C(4), are -68.7 (5)° and -77.2(4)° for molecules (a) and (b) of 8,2'-EA, respectively, and -65.7(4)° for 8,2'-MA, and are in high-anti conformation (x; -90°--50°). The deoxyribose ring of 8,2'-MA takes the C(3')-exo, C(4')-endo twist pucker, and the conformation about the C(4')-C(5') bond is gauche^+.In contrast, both deoxyribose rings of 8,2'-EA exhibit C(1')-exo envelope puckering, and the conformation about the C(4')-C(5') bond is gauche^+ for molecule (a) and trans for molecule (b). ^1H-NMR data indicate that both of the cyclonucleosides in solution exist in the equilibrium of several sugar and exocyclic conformations. 8,2'-EA adopts two different conformations, even around the glycosidic bound.

• 公益社団法人日本薬学会の論文
• 1992-01-25

著者

• 冨田 研一

  Faculty of Pharmaceutical Sciences, Osaka University

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 松田 彰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 上田 亨

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 山縣 ゆり子

  Faculty of Pharmaceutical Sciences, Osaka University

• 山縣 ゆり子

  阪大薬

• 山縣 ゆり子

  Faculty Of Pharmaceutical Sciences Osaka University

• 唯井 博之

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 上田 亨

  北海道大学薬学部

• 冨田 研一

  Faculty Of Pharmaceutical Sciences Osaka University

• 唯井 博之

  Faculty Of Pharmaceutical Sciences Hokkaido University

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