A general synthesis of C8-arylpurine phosphoramidites.
A general scheme for the synthesis of C8-arylpurine phosphoramidites has been developed. C8-Arylation of C8-bromo-2'-deoxyguanosine is the key step and has been achieved through the use of a Suzuki coupling. Since the coupling reaction is conducted under aqueous conditions, it is unnecessary to protect and then deprotect the hydroxyl groups, thus saving several steps and improving overall yields. Once the C8-arylgroup is introduced, the glycosidic bond becomes very sensitive to acid catalyzed cleavage. Protection of the amino groups as the corresponding N,N-dimethylformamidine derivative improves stability of the derivatives. Synthetic C8-arylpurines were successfully used to prepare synthetic oligonucleotides.
West Virginia University, Department of Basic Pharmaceutical Sciences, Morgantown, WV 26506, USA. vorasit.v@chula.ac.th
Vorasit
V
Vongsutilers
Jonathan R
JR
Daft
Kevin H
KH
Shaughnessy
Peter M
PM
Gannett
D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D011687:Purines