88508-63-8Relevant academic research and scientific papers
Synthesis and enzymatic deprotection of biodegradably protected dinucleoside-2′,5′-monophosphates: 3-(Acetyloxy)-2,2- bis(ethoxycarbonyl)propyl phosphoesters of 3′-O-(acyloxymethyl)adenylyl- 2′,5′-adenosines
Kiuru, Emilia,Ora, Mikko,Beigelman, Leonid,Blatt, Lawrence,Loennberg, Harri
experimental part, p. 266 - 286 (2011/10/05)
As a first step towards a viable prodrug strategy for short oligoribonucleotides, such as 2-5A and its congeners, adenylyl-2′, 5′-adenosines bearing a 3-(acetyloxy)-2,2-bis(ethoxycarbonyl)propyl group at the phosphate moiety, and an (acetyloxy)methyl- or a (pivaloyloxy)methyl- protected 3′-OH group of the 2′-linked nucleoside have been prepared. The enzyme-triggered removal of these protecting groups by hog liver carboxyesterase at pH 7.5 and 37° has been studied. The (acetyloxy)methyl group turned out to be too labile for the 3′-O-protection, being removed faster than the phosphate-protecting group, which results in 2′,5′- to 3′,5′-isomerization of the internucleosidic phosphoester linkage. In addition, the starting material was unexpectedly converted to the 5′-O-acetylated derivative. (Pivaloyloxy)methyl group appears more appropriate for the purpose. The fully deprotected 2′,5′-ApA was accumulated as a main product, although, even in this case, the isomerization of the starting material takes place.
Synthesis of [18F]-labeled adenosine analogues as potential PET imaging agents
Alauddin, Mian M.,Fissekis, John D.,Conti, Peter S.
, p. 805 - 814 (2007/10/03)
The syntheses of adenosine analogues, 2′-deoxy-2′-[ 18F]fluoro-9-β-D-arabinofuranosyladenine ([18F]-FAA) and 3′-deoxy-3′-[18F]fluoro-9-β -D-xylofuranosyladenine ([18F]-FXA) are reported. Adenosine (1) was converted to its methoxytrityl derivatives 2 and 3 as a mixture. After separation, these derivatives were converted to their respective triflates 4 and 5. Each triflate was reacted with tetrabutylammonium[18F] fluoride to produce 6b or 7b, which by acidic hydrolysis yielded compounds 8b and 9b. Crude preparations were purified by HPLC to obtain the desired pure products. The radiochemical yields were 10-18 % decay corrected (d.c.) for 8b and 30-40% (d.c.) for 9b in 4 and 3 runs, respectively. Radiochemical purity was > 99% and specific activity was > 74 GBq/μmol at the end of synthesis (EOS). The synthesis time was 90-95 min from the end of bombardment (EOB). Copyright
