1,N-6-Etheno-7-deaza-2,8-diazaadenosine: syntheses, properties and conversion to 7-deaza-2,8-diazaadenosine

Autor(en): Lin, WQ
Li, H
Ming, X
Seela, F
Stichwörter: 3,5-CYCLIC PHOSPHATE; 3,N-4-ETHENO; ADENOSINE; BIOLOGICAL-ACTIVITY; Chemistry; Chemistry, Organic; CRYSTAL; DERIVATIVES; DNA; PYRAZOLOPYRIMIDINE NUCLEOSIDES
Erscheinungsdatum: 2005
Herausgeber: ROYAL SOC CHEMISTRY
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
Volumen: 3
Ausgabe: 9
Startseite: 1714
Seitenende: 1718
Zusammenfassung: 
1,N-6-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-beta-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-6-etheno-2-azaadenosine (3a) (495 nm). A conformational analysis was performed in the solid state and in solution.
ISSN: 14770520
DOI: 10.1039/b418849g

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