Aqueous-phase Sonogashira alkynylation to synthesize 5-substituted pyrimidine and 8-substituted purine nucleosides.
In this unit, an efficient method for the synthesis of alkyne-modified nucleosides in an aqueous solvent system is described. The method allows direct palladium-catalyzed alkynylation of readily available unprotected 8-bromo-2'-deoxyguanosine (8-BrdG), 8-bromo-2'-deoxyadenosene (8-BrdA), 8-bromoadenosine (8-BrA), and 5-iodo-2'-deoxyuridine (5-IdU) precursors. The optimal catalyst is derived from palladium acetate, tri-(2,4-dimethyl-5-sulfonatophenyl)phosphane (TXPTS), and CuI.
Department of Chemistry, The University of Alabama, Tuscaloosa, AL, USA.
Joon Hyung
JH
Cho
Kevin H
KH
Shaughnessy
D000480:Alkynes / Q000138:chemical synthesis*; D001557:Benzenesulfonates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003849:Deoxyguanosine / Q000031:analogs & derivatives / Q000737:chemistry; D007065:Idoxuridine / Q000031:analogs & derivatives / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*
C439365:8-bromo-2'-deoxyguanosine; D000480:Alkynes; D001557:Benzenesulfonates; D007454:Iodides; D010720:Phosphines; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; C029954:5'-deoxy-5'-iodouridine; D010165:Palladium; D003300:Copper; C073870:cuprous iodide; D003849:Deoxyguanosine; D007065:Idoxuridine