A novel polymer supported approach to nucleoside modification

The Journal of Organic Chemistry
Suyeal Bae, Mahesh K Lakshman

Abstract

Polymer-supported O(6)-(benzotriazol-1-yl)inosine derivatives (Pol-I and Pol-dI) have been synthesized reasonably effectively via reaction of nucleoside phosphonium salts with polymer-linked HOBt (Pol-HOBt). In constast to solution chemistry, use of polymer-supported BOP (Pol-BOP) did not lead to efficient nucleoside loading. Presence of the nucleosides on the support could be readily detected by MAS NMR. Exposure of the polymer-supported nucleosides, Pol-I and Pol-dI, to alcohol, phenol, thiol and amine nucleophiles caused cleavage from the support leading directly to the C-6 modified nucleoside analogues. To our knowledge, these are the first examples of the application of such technology for nucleoside modification. Where possible, results of reactions with the polymer-supported nucleosides are compared to those from solution chemistry, providing insight into the differences between the two techniques. These new polymer-supported nucleosides can be conveniently utilized for diversity-oriented synthesis.

References

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Dec 12, 2001·The Journal of Organic Chemistry·E A Véliz, P A Beal
Feb 15, 2002·Organic Letters·Yongseok ChoiVictor E Marquez
Mar 27, 2004·Nucleosides, Nucleotides & Nucleic Acids·Zlatko JanebaMorris J Robins
Apr 28, 2006·Angewandte Chemie·Pallavi LagisettyMahesh K Lakshman
Jan 25, 2007·Journal of the American Chemical Society·Suyeal Bae, Mahesh K Lakshman
Nov 30, 2007·The Journal of Organic Chemistry·Zhao-Kui WanTarek S Mansour
Jan 22, 2008·The Journal of Organic Chemistry·Suyeal Bae, Mahesh K Lakshman

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Citations

Oct 8, 2009·Journal of the American Chemical Society·Lirui Guan, Marc M Greenberg
Jul 5, 2012·The Journal of Organic Chemistry·Mahesh K LakshmanJan Balzarini
Mar 20, 2010·The Journal of Organic Chemistry·Mahesh K LakshmanBilly W Day
Sep 18, 2010·Organic Letters·Hari Prasad Kokatla, Mahesh K Lakshman
Jul 8, 2009·Organic & Biomolecular Chemistry·Mahesh K Lakshman, Josh Frank
May 4, 2013·Nucleosides, Nucleotides & Nucleic Acids·Peng Zhao, Lihe Zhang
Oct 17, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sakilam SatishkumarMahesh K Lakshman
Jan 1, 2009·European Journal of Organic Chemistry·Mahesh K LakshmanAmit Kumar
Jun 16, 2012·Current Protocols in Nucleic Acid Chemistry·Hari Prasad Kokatla, Mahesh K Lakshman
Oct 4, 2019·European Journal of Organic Chemistry·Tashrique A KhandakerMahesh K Lakshman
May 1, 2010·European Journal of Organic Chemistry·Amit KumarMahesh K Lakshman
Feb 8, 2021·European Journal of Medicinal Chemistry·Xia LinWeisen Lan
Nov 12, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sakilam SatishkumarMahesh K Lakshman
Aug 21, 2012·Organic Letters·Gui-Rong QuJohn S Fossey
Dec 15, 2021·The Journal of Organic Chemistry·Dellamol SebastianMahesh K Lakshman

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