Document Type
Article
Publication Date
2009
College/Unit
School of Pharmacy
Department/Program/Center
Pharmaceutical Sciences
Abstract
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.
Digital Commons Citation
Vongsutilers, Vorasit; Daft, Jonathan R.; Shaughnessy, Kevin H.; and Gannett, Peter M., "A General Synthesis of C8-Arylpurine Phosphoramidite" (2009). Faculty & Staff Scholarship. 2829.
https://researchrepository.wvu.edu/faculty_publications/2829
Source Citation
Vongsutilers, V., Daft, J., Shaughnessy, K., & Gannett, P. (2009). A General Synthesis of C8-Arylpurine Phosphoramidites. Molecules, 14(9), 3339–3352. https://doi.org/10.3390/molecules14093339
Comments
This is an open access article distributed under the Creative Commons Attribution License