Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer’s chlorosugar
作者： Subhendu Sekhar Bag , Sangita Talukdar , S.J. Anjali
DOI: 10.1016/J.BMCL.2016.02.078
关键词:
摘要: We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center Hoffer's chlorosugar with various 5-substituted tetrazoles in THF presence K2CO3 proceeds regioselectivity N2-tetrazoles stereoselectivity α-chlorosugar very good yield. stereoelectronic steric effects play crucial role for observed outcome which is also supported from theoretical (DFT) study. methodology simple, eco-compatible tetrazolyl might find applications decorating biotechnological based material science applications.
sci-hub.se 参考文章(47)
Wolfram Saenger, Principles of Nucleic Acid Structure ,(1983)
Subhendu Sekhar Bag, Sangita Talukdar, Suman Kalyan Das, Design and Synthesis of Triazolyl‐Donor/Acceptor Unnatural Nucleosides and Oligonucleotide Probes Containing Triazolyl‐Phenanthrene Nucleoside Current protocols in human genetics. ,vol. 58, ,(2014) , 10.1002/0471142700.NC0132S58
Vyacheslav V Filichev, Maxim V Jasko, Alexander A Malin, Vadim Yu Zubarev, Vladimir A Ostrovskii, Synthesis of novel thymidine derivatives containing a polycyclic tetrazole linker Tetrahedron Letters. ,vol. 43, pp. 1901- 1903 ,(2002) , 10.1016/S0040-4039(02)00134-X
Ming Wah Wong, Regis Leung-Toung, Curt Wentrup, Tautomeric equilibrium and hydrogen shifts of tetrazole in the gas phase and in solution Journal of the American Chemical Society. ,vol. 115, pp. 2465- 2472 ,(1993) , 10.1021/JA00059A048
Ross H. Durland, T. Sudhakar Rao, Veeraiah Bodepudi, Dale M. Seth, Krishna Jayaraman, Ganapathi R. Revankar, Azole substituted oligonucleotides promote antiparallel triplex formation at non-homopurine duplex targets Nucleic Acids Research. ,vol. 23, pp. 647- 653 ,(1995) , 10.1093/NAR/23.4.647
J. T. Witkowski, Roland K. Robins, Robert W. Sidwell, Lionel N. Simon, Design, synthesis, and broad spectrum antiviral activity of 1-.beta.-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides Journal of Medicinal Chemistry. ,vol. 15, pp. 1150- 1154 ,(1972) , 10.1021/JM00281A014
Anil K. Bhattacharya, Robert K. Ness, Hewitt G. Fletcher, 2-Deoxy-D-erythro-pentose. IX.1 Some Relationships among the Rotations of Acylated Aldopentoses, Aldopentosyl Halides, and Anhydropentitols Journal of Organic Chemistry. ,vol. 28, pp. 428- 435 ,(1963) , 10.1021/JO01037A037
V. A. Ostrovskii, R. E. Trifonov, E. A. Popova, Medicinal chemistry of tetrazoles Russian Chemical Bulletin. ,vol. 61, pp. 768- 780 ,(2012) , 10.1007/S11172-012-0108-4
Mohindar S. Poonian, Eugene F. Nowoswiat, John F. Blount, Thomas H. Williams, Ross G. Pitcher, Michael J. Kramer, Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents Journal of Medicinal Chemistry. ,vol. 19, pp. 286- 290 ,(1976) , 10.1021/JM00224A016
Tim Efthymiou, Wei Gong, Jean-Paul Desaulniers, Chemical Architecture and Applications of Nucleic Acid Derivatives Containing 1,2,3-Triazole Functionalities Synthesized via Click Chemistry Molecules. ,vol. 17, pp. 12665- 12703 ,(2012) , 10.3390/MOLECULES171112665