Выходит 6 номеров в год
ISSN Печать: 1045-4403
ISSN Онлайн: 2162-6502
Indexed in
The Synthesis of C8-Aryl Purines, Nucleosides and Phosphoramidites
Краткое описание
C8-Aryl purines, their nucleosides, and phosphoramidites has been synthetic targets for more than 60 years. Interest in these compounds stems from their utility as fluorescent markers, they have therapeutic uses, are biomarkers, biomolecular probes, supramolecular building blocks, and for conformational studies. Until recently, the selective arylation of the C8-position of purines has been a challenging task. Several approaches have been explored including building them up from a pyrimidine or selective C8-modification of an unsubstituted purine. Neither of these approaches has proven to have broad scope. The discovery that C8-aryl purine nucleosides can be made via the Suzuki cross-coupling reaction has allowed a diverse array of analogues to be prepared and, in turn, the corresponding phosphoramidites. The latter is particularly significant as C8-aryl purine adducts are a major mutation observed from aromatic carcinogens and ready access to C8-aryl phosporamidites will facilitate the synthesis and study of C8-aryl purine biomarkers and modified oligonucleotides.
-
Seidu-Larry Salifu, Krieg Bettina, Hirsch Markus, Helm Mark, Domingo Olwen, A modified guanosine phosphoramidite for click functionalization of RNA on the sugar edge, Chemical Communications, 48, 89, 2012. Crossref
-
Thomsen Nissa M., Vongsutilers Vorasit, Gannett Peter M., ChemInform Abstract: The Synthesis of C8-Aryl Purines, Nucleosides, and Phosphoramidites, ChemInform, 43, 17, 2012. Crossref
-
Dolzhenko Anton V., Kalinina Svetlana A., Kalinin Dmitrii V., A novel multicomponent microwave-assisted synthesis of 5-aza-adenines, RSC Advances, 3, 36, 2013. Crossref
-
Gigante Alba, Priego Eva-María, Sánchez-Carrasco Paula, Ruiz-Pérez Luis Miguel, Vande Voorde Johan, Camarasa María- José, Balzarini Jan, González-Pacanowska Dolores, Pérez-Pérez María-Jesús, Microwave-assisted synthesis of C-8 aryl and heteroaryl inosines and determination of their inhibitory activities against Plasmodium falciparum purine nucleoside phosphorylase, European Journal of Medicinal Chemistry, 82, 2014. Crossref
-
Merino Pedro, Delso Ignacio, Tejero Tomás, Ghirardello Mattia, Juste-Navarro Verónica, Nucleoside Diphosphate Sugar Analogues that Target Glycosyltransferases, Asian Journal of Organic Chemistry, 5, 12, 2016. Crossref
-
Shaughnessy Kevin, Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides, Molecules, 20, 5, 2015. Crossref
-
Elgemeie Galal H., Mohamed Reham A., Microwave chemistry: Synthesis of purine and pyrimidine nucleosides using microwave radiation, Journal of Carbohydrate Chemistry, 38, 1, 2019. Crossref
-
Nazarian Zohreh, Dabiri Minoo, Orthoesters: Multiple Role Players in Organic Synthesis, ChemistrySelect, 5, 15, 2020. Crossref
-
Balasubramaniyam Thananjeyan, Oh Kwnag-Im, Jin Ho-Seong, Ahn Hye-Bin, Kim Byeong-Seon, Lee Joon-Hwa, Non-Canonical Helical Structure of Nucleic Acids Containing Base-Modified Nucleotides, International Journal of Molecular Sciences, 22, 17, 2021. Crossref