1,N6-Etheno-7-deaza-2,8-diazaadenosine: syntheses, properties and conversion to 7-deaza-2,8-diazaadenosine.
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.
Lin
Wenqing
W
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, 49069, Osnabrück, Germany.
Li
Hong
H
Ming
Xin
X
Seela
Frank
F
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
C511521:1,N6-etheno-7-deaza-2,8-diazaadenosine; C511522:7-deaza-2,8-diazaadenosine; D001372:Aza Compounds; D000241:Adenosine