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A General Synthesis of C8-Arylpurine Phosphoramidites
West Virginia University, Department of Basic Pharmaceutical Sciences, P.O. Box 9530, Morgantown, WV 26506, USA
Department of Chemistry and Center for Green Manufacturing, The University of Alabama, Box 870336, Tuscaloosa, Alabama 35487-0336, USA
* Author to whom correspondence should be addressed.
Received: 10 July 2009; in revised form: 20 August 2009 / Accepted: 27 August 2009 / Published: 2 September 2009
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.
Keywords: C8-arylpurine synthesis; Suzuki coupling; phosphoramidite
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Vongsutilers, V.; Daft, J.R.; Shaughnessy, K.H.; Gannett, P.M. A General Synthesis of C8-Arylpurine Phosphoramidites. Molecules 2009, 14, 3339-3352.
Vongsutilers V, Daft JR, Shaughnessy KH, Gannett PM. A General Synthesis of C8-Arylpurine Phosphoramidites. Molecules. 2009; 14(9):3339-3352.
Vongsutilers, Vorasit; Daft, Jonathan R.; Shaughnessy, Kevin H.; Gannett, Peter M. 2009. "A General Synthesis of C8-Arylpurine Phosphoramidites." Molecules 14, no. 9: 3339-3352.