Abstract
A new simple and convenient approach to the synthesis of oligonucleotides containing pyrene or cholesterol moieties is described. The approach does not require a special phosphoramidite reagent as it is based on Staudinger reaction between an azidoalkyl derivative of either pyrene or cholesterol and a polymer-supported internucleoside 2-cyanoethyl phosphite, which is formed during phosphoramidite condensation.
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N. Venkatesan, S. J. Kim, B. H. Kim, Curr. Med. Chem., 2003, 10, 1973–1991.
A. J. A. Cobb, Org. Biomol. Chem., 2007, 5, 3260–3275.
K. Yamana, H. Zako, K. Asazuma, R. Iwase, H. Nakano, A. Murakami, Angew. Chem., Int. Ed., 2001, 40, 1104–1106.
V. A. Korshun, D. A. Stetsenko, M. J. Gait, J. Chem. Soc., Perkin Trans. 1, 2002, 41, 1092–1104.
M. W. Reed, E. A. Lukhtanov, V. V. Gorn, D. D. Lucas, J. H. Zhou, S. B. Pai, Y. Cheng, R. B. Meyer, Jr., J. Med. Chem., 1995, 38, 4587–4596.
Y. J. Seo, H. S. Jeong, E.-K. Bang, G. T. Hwang, J. H. Jung, S. K. Jang, B. H. Kim, Bioconjugate Chem., 2006, 17, 1151–1155.
T. Shiraishi, P. E. Nielsen, Bioconjugate Chem., 2012, 23, 196–202.
R. L. Letsinger, M. E. Schott, J. Am. Chem. Soc., 1981, 103, 7394–7396.
J. Nielsen, M. H. Caruthers, J. Am. Chem. Soc., 1988, 110, 6275–6276.
D. A. Stetsenko, M. S. Kupryushkin, D. V. Pyshnyi, Application for a RF patent No. 2014117293 on 29.04.2014.
M. S. Kupryushkin, M. D. Nekrasov, D. A. Stetsenko, D. V. Pyshnyi, Org. Lett., 2014, 16, 2842–2845.
M. E. Jung, S. Ouk, D. Yoo, C. L. Sawyers, C. Chen, C. Tran, J. Wongvipat, J. Med. Chem., 2010, 53, 2779–2796.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1678–1681, July, 2015.
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Kupryushkin, M.S., Apukhtina, V.S., Vasilyeva, S.V. et al. A new simple and convenient method for preparation of oligonucleotides containing a pyrene or a cholesterol moiety. Russ Chem Bull 64, 1678–1681 (2015). https://doi.org/10.1007/s11172-015-1059-3
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DOI: https://doi.org/10.1007/s11172-015-1059-3