A nucleotide dimer synthesis without protecting groups using montmorillonite as catalyst

Nucleosides, Nucleotides and Nucleic Acids

Volumn 31, Issue 7, 2012, Pages 536-566

  Joshi, Prakash C ^a   Aldersley, Michael F ^a   Zagorevskii, Dmitri V ^b   Ferris, James P ^a  

^a Rensselaer Polytechnic Institute   (United States)

^b RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

green chemistry; Montmorillonite; phosphorimidazolide; RNA dimers

Indexed keywords

D DIMER; DEOXYRIBONUCLEOSIDE; DIMER; MONTMORILLONITE; RIBONUCLEOSIDE 5' PHOSPHORIMIDAZOLIDE; RIBONUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; DIMER SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; OLIGOMERIZATION;

BENTONITE; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; DIMERIZATION; GREEN CHEMISTRY TECHNOLOGY; IMIDAZOLES; MODELS, MOLECULAR; NUCLEOSIDES; NUCLEOTIDES;

EID: 84864654622     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2012.701787     Document Type: Article

References (23)

1. Huang, W., and, Ferris, J. P. 2006. One-step, regioselective synthesis of up to 50-mers of RNA oligomers by montmorillonite catalysis. J. Am. Chem. Soc., 128 (27): 8914-8919. (Pubitemid 44061549)
2. Zagorevskii, D. V., Aldersley, M. F., and, Ferris, J. P. 2006. MALDI analysis of oligonucleotides directly from montmorillonite. J. Am. Soc. Mass. Spectr., 17 (9): 1265-1270. (Pubitemid 44292010)
3. Ferris, J. P. 2006. Montmorillonite-catalyzed formation of RNA oligomers: The possible role of catalysis in the origins of life. Phil. Trans. R. Soc. B: Biol. Sc., 361 (l474): 1777-1786. (Pubitemid 44580380)
4. Joshi, P. C., Aldersley, M. F., Delano, J. W., and, Ferris, J. P. 2009. Mechanism of montmorillonite catalysis in the formation of RNA oligomers. J. Am. Chem. Soc., 131 (37): 13369-13374.
5. Miyakawa, S., and, Ferris, J. P. 2003. Sequence-and regioselectivity in the montmorillonite-catalyzed synthesis of RNA. J. Am. Chem. Soc., l25 (27): 8202-8208. (Pubitemid 36828583)
6. Braibante, M. E.F., Braibante, H. T.S., de Carvalho Tavares, L., Rohte, S. F., Costa, C. C., Morel, A. F., Stüker, C. Z., and, Burrow, R. A. 2007. Efficient regiocontrolled synthesis and antimicrobial activity of pyrazoles. Synthesis, 16: 2485-2490. (Pubitemid 47338896)
7. Choudary, B. M., Sharma, G. V.M., and, Bharathi, P. 1989. Highly-selective Montmorillonite catalyst for hydrogenation of alkynes, alkenynes and alkadienes. Chem. Int. Ed Engl., 28 (4): 465-466. and Angewandte Chemie, 1989, 101 (4), 5067
8. Varma, R. S., Naicker, K. P., and, Aschberger, J. 1999. A facile preparation of alkyl azides from alkyl bromides and sodium azide using 18-crown-6 ether doped clay. Synthetic. Commun., 29 (16): 2823-2830. (Pubitemid 29287900)
9. Reese, C. B. 2005. Oligo-and poly-nucleotides: 50 years of chemical synthesis. Org. Biomol.Chem, 3 (2l): 3851-3868. (Pubitemid 41640794)
10. Bazzanini, R., Gouy, M.-H., Peyrottes, S., Gosselin, G., Perigaud, C., and, Manfredini, S. 2005. Influence of probe structure on unique (regiospecific) cleavage of RNA by RNase H. Nucleosides, Nucleotides Nucleic Acids, 24 (10-12): 1635-1649.
11. Metelev, V. G., Zayakina, G. V., Ryabushenko, I. L., Krynetskaya, N. F., Romanova, E. A., Oretskaya, T. S., and, Shabarova, Z. A. 1988. Influence of probe structure on unique (regiospecific) cleavage of RNA by RNase H. FEBS Letters, 226 (2): 232-234.
12. Harada, K., and, Orgel, L. E. 1991. The cyclization of arabinosyladenine-5-phosphorimidazolide. J. Mol. Evol., 32: 358-359.
13. Aldersley, M. F., Joshi, P. C., Price, J. D., and, Ferris, J. P. 2011. The role of montmorillonite in its catalysis of RNA synthesis. Appl. Clay Sci., 54 (1): 1-14.
14. Velikyan, I., Acharya, S., Trifonova, A., Foeldesi, A., and, Chattopadhyaya, J. 2001. The pK a's of 2-hydroxyl group in nucleosides and nucleotides. J. Am. Chem. Soc., 123 (12): 2893-2894. (Pubitemid 32910720)
15. Saenger, W. 1984. Principles of Nucleic Acid Structure, New York: Springer-Verlag.
16. Yu, Y., Nakamura, D., DeBoyace, K., Neisius, A. W., and, McGown, L. B. 2008. Tunable thermoassociation of binary guanosine gels. J. Phys. Chem. B., 112 (4): 1130-1134. (Pubitemid 351257477)
17. Kaucher, M. S., Lam, Y.-F., Pieraccini, S., Gottarelli, G., and, Davis, J. T. 2004. Using diffusion NMR to characterize guanosine self-association: Insights into structure and mechanism. Chem Eur. J., 11 (1): 164-173. (Pubitemid 40065632)
18. Qin, H., Ren, J., Wang, J., Luedtke, N. W., and, Wang, E. 2010. G-quadruplex-modulated fluorescence detection of potassium in the presence of a 3500-fold excess of sodium ions. Anal. Chem., 82 (19): 8356-8360. and references cited therein
19. Joyce, G. F., and, Orgel, L. E. 2006. Progress toward understanding the origin of the RNA world. In The RNAWorld, 3rd edn, Edited by: Gesteland, R. F., Cech, T. R. and Atkins, J. F. 23-56. Cold Spring Harbor Laboratory Press.
20. Ikemoto, T., Haze, A., Hatano, H., Kitarnoto, Y., Ishida, M., and, Nara, K. 1995. Phosphorylation of nucleosides with phosphorus oxychloride in trialkyl phosphate. Chem. Pharm. Bull., 43: 210-215.
21. Joyce, G. F., Inoue, T., and, Orgel, L. E. 1984. Non-enzymic template-directed synthesis on RNA random copolymers. Poly(C, U) templates. J. Mol. Biol., 176 (2): 279-306.
22. Joshi, P. C., Ferris, J. P., and, Pitsch, S. 2000. Homochiral selection in the montmorillonite· catalyzed and uncatalyzed prebiotic synthesis of RNA. Chem. Commun. (Cambridge), 24: 2497-2498. (Pubitemid 32001367)
23. Spartan '06 and Spartan '10. Irvine, CA: Wavefunction, Inc.