Synthesis, mechanism and fluorescence properties of 8-(aryl)-3-beta-D-ribofuranosylimidazo[2,1-i]purine 5'-phosphate derivatives.
The synthesis of new fluorescent nucleotides is described. This synthesis comprises two parallel reactions, the Kornblum oxidation and imidazole formation, which lead to 8-(aryl)-3-beta-D-ribofuranosylimidazo[2,1-i]purine 5'-phosphates 2 from AMP or ATP. A detailed mechanism is proposed based on monitoring the reaction by 1H- and 13C-NMR spectroscopy, MS, FAB, HPLC, and pH meter. The spectral and fluorescent properties of the new derivatives at various pH values are described. Excitation and emission maxima for 3 were observed at 290 and 420 nm, respectively, in both basic and neutral media. In acidic media, the emission maximum shifted to 410 nm, however, the fluorescence intensity increased 1.5-fold. ATP analogues 2b and 3b exhibited relative stability regarding hydrolysis by type II ATPDase. Compound 3b is relatively chemically stable at pH 10.4 and 7.4.
Fischer
B
B
Department of Chemistry, Gonda-Goldscmied Medical Research Center, Bar-Ilan University, Ramat-Gan, Israel.
Kabha
E
E
Gendron
F P
FP
Beaudoin
A R
AR
D000249:Adenosine Monophosphate / Q000737:chemistry*; D000255:Adenosine Triphosphate / Q000737:chemistry*; D000818:Animals; D001081:Apyrase / Q000378:metabolism; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009005:Monosaccharides / Q000138:chemical synthesis*; D011687:Purines / Q000138:chemical synthesis*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013154:Spleen / Q000502:physiology
D009005:Monosaccharides; D011687:Purines; D000249:Adenosine Monophosphate; D000255:Adenosine Triphosphate; D001081:Apyrase