Journal of the American Chemical Society, Vol.117, No.47, 11669-11672, 1995
Syntheses of (6,7-N-15)-Adenosine, (6,7-N-15)-2’-Deoxyadenosine, and (7-N-15)-Hypoxanthine
We have developed a high-yield route for the synthesis of [7-N-15]-hypoxanthine in four steps in an overall yield of 81%. This procedure uses [N-15]-sodium nitrite as the N-15 source and an inexpensive pyrimidine to provide an economical route to this useful N-15-labeled intermediate. Conversion to [7-N-15]-6-chloropurine followed by enzymatic transglycosylation gives the corresponding ribo- and 2’-deoxyribonucleosides. Ammonolysis of the 6-chloro moiety to give the [6,7-N-15]-labeled nucleosides is effected simply and in high yield using 2 equiv of [N-15]-ammonium chloride and 3 equiv of potassium bicarbonate.
Keywords:NITROGEN-15-LABELED OLIGODEOXYNUCLEOTIDES;N-15 NMR;ENZYMATIC-SYNTHESIS;ADENINE N1;BASE-PAIR;DEOXYNUCLEOSIDES;DEOXYADENOSINE;OLIGONUCLEOTIDES;NUCLEOSIDES;CONVERSION