Abstract
In contrast to tetrazole, pyridine hydrochloride/imidazole converts nucleoside phosphoramidites to intermediates that show a high preference for phosphitilating hydroxyl groups relative to nucleoside amino groups. Use of this activating agent and incorporation of a pyridine hydrochloride/aniline wash step in the synthetic cycles permit synthesis of mixed base twenty-mer oligonucleotides from nucleoside reagents containing unprotected amino groups. This approach should be useful for the synthesis of oligonucleotide analogues containing substituents sensitive to reagents used in conventional deblocking steps. Pyridine hydrochloride itself is an effective reagent for activating nucleoside methylphosphonoamidites and ribonucleoside phosphoramidites, as well as deoxyribonucleoside phosphoramidites, when high O/N selectivety is not needed.
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Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Alul R. H., Singman C. N., Zhang G. R., Letsinger R. L. Oxalyl-CPG: a labile support for synthesis of sensitive oligonucleotide derivatives. Nucleic Acids Res. 1991 Apr 11;19(7):1527–1532. doi: 10.1093/nar/19.7.1527. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Barone A. D., Tang J. Y., Caruthers M. H. In situ activation of bis-dialkylaminophosphines--a new method for synthesizing deoxyoligonucleotides on polymer supports. Nucleic Acids Res. 1984 May 25;12(10):4051–4061. doi: 10.1093/nar/12.10.4051. [DOI] [PMC free article] [PubMed] [Google Scholar]