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1,N6-Etheno-7-deaza-2,8-diazaadenosine: syntheses, properties and conversion to 7-deaza-2,8-diazaadenosine.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2005 May 07; Vol. 3 (9), pp. 1714-8. Date of Electronic Publication: 2005 Mar 30. - Publication Year :
- 2005
-
Abstract
- 1,N6-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 x 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.
Details
- Language :
- English
- ISSN :
- 1477-0520
- Volume :
- 3
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 15858655
- Full Text :
- https://doi.org/10.1039/b418849g