1,N6-Etheno-7-deaza-2,8-diazaadenosine: syntheses, properties and conversion to 7-deaza-2,8-diazaadenosine
Lin, Wenqing; Li, Hong; Ming, Xin; Seela, Frank; Lin Wenqing; Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück; Center for Nanotechnology (CeNTech); Li Hong; Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück; Center for Nanotechnology (CeNTech); Ming Xin; Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück; Center for Nanotechnology (CeNTech); Seela Frank; Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück; Center for Nanotechnology (CeNTech)
Журнал:
Organic & Biomolecular Chemistry
Дата:
2005
Аннотация:
1,N<sup>6</sup>-Etheno-7-deaza-2,8-diazaadenosine (4) was synthesized from 8-aza-7-deazaadenosine (6) in 64% overall yield. The starting material 6 was obtained by the direct glycosylation of 8-aza-7-deazaadenine (7) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (8) (NO2 CH3, BF3·Et2O; 77% yield). Compound 4 was transformed into 7-deaza-2,8-diazaadenosine (5). The fluorescence of compound 4 shows an emission maximum at 531 nm (phosphate buffer; pH 7.0), which is bathochromically shifted compared to 1,N<sup>6</sup>-etheno-2-azaadenosine (3a) (495 nm). A conformational analysis was performed in the solid state and in solution.
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