Next Article in Journal
Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones
Previous Article in Journal
Synthesis and Pharmacological Screening of Several Aroyl and Heteroaroyl Selenylacetic Acid Derivatives as Cytotoxic and Antiproliferative Agents
Molecules 2009, 14(9), 3339-3352; doi:10.3390/molecules14093339
Article

A General Synthesis of C8-Arylpurine Phosphoramidites

1
,
1
,
2
 and
1,*
Received: 10 July 2009 / Revised: 20 August 2009 / Accepted: 27 August 2009 / Published: 2 September 2009
Download PDF [265 KB, uploaded 18 June 2014]

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 C8-arylpurine synthesis; Suzuki coupling; phosphoramidite
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Vongsutilers, V.; Daft, J.R.; Shaughnessy, K.H.; Gannett, P.M. A General Synthesis of C8-Arylpurine Phosphoramidites. Molecules 2009, 14, 3339-3352.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert