214918-86-2Relevant academic research and scientific papers
Unexpected reactivity of N2-benzylidene guanosine derivatives
Mons, Stephane,Lebeau, Luc,Mioskowski, Charles
, p. 9183 - 9186 (2007/10/03)
Guanosine derivatives masked at the sugar are protected at N2 by a benzylideneamine group for the first time. The free 5'-hydroxyl function reveals to be incompatible with the N2-protective group that is then rapidly hydrolyzed to regenerate the free exocyclic amine.
Synthesis of enzymatically stable analogues of GDP for binding studies with transducin, the G-protein of the visual photoreceptor
Vincent, Stephane,Grenier, Sonya,Valleix, Alain,Salesse, Christian,Lebeau, Luc,Mioskowski, Charles
, p. 7244 - 7257 (2007/10/03)
The synthesis of five enzymatically stable analogues of guanosine diphosphate (GDP) has been carried out. The pyrophosphate moiety was mimicked in turn by the malonate, the acetophosphonate, the phosphonoacetate, the methylene-bis-phosphonate, and the imidodiphosphate groups. All the compounds were prepared via the synthesis of a transient fully protected nucleoside diphosphate analogue, and the final deprotection step was achieved by catalytic hydrogenolysis. The biological properties of the compounds have been evaluated toward transducin, the G-protein of the visual photoreceptor. Three guanosine imidodiphosphate derivatives bearing a linker at different positions on the sugar and on the base were then prepared and evaluated, giving some insight into the GDP binding site of transducin.
