Oligonucleotide synthesis using ionic liquids as soluble supports

Nucleosides, Nucleotides and Nucleic Acids

Volumn 26, Issue 10-12, 2007, Pages 1287-1293

  Donga, Robert A ^a   Hassler, Matthew ^a   Chan, Tak Hang ^a   Damha, Masad J ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Oligonucleotides; Soluble ionic tags

Indexed keywords

IONIC LIQUID; OLIGONUCLEOTIDE;

ARTICLE; COST EFFECTIVENESS ANALYSIS; PURIFICATION; SYNTHESIS;

IONIC LIQUIDS; NUCLEOSIDES; OLIGONUCLEOTIDES;

EID: 36949001120     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701530533     Document Type: Article

References (18)

1. Fodor, S.P.; Rava, R.P.; Huang, X.C.; Pease, A.C.; Holmes, C.P.; Adams, C.L. Multiplexed biochemical assays with biological chips. Nature 1993, 364, 555-556.
2. Barone, A.D.; Beecher, J.E.; Bury, P.A.; Chen, C.; Doede, T.; Fidanza, J.A.; McGall, G.H. Photolithographic synthesis of high-density oligonucleotide probe arrays. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 525-531.
3. Damha, M.J.; Ogilvie, K.K. Oligoribonucleotide synthesis. The silyl-phosphoramidite method. Methods in Molecular Biology 1993, 20, 81-114.
4. a) Pon, R.T.; Yu, S.; Guo, Z.; Deshmukh, R.; Sanghvi, Y.S. Reusable solid-phase supports for oligonucleotides and antisense therapeutics. J. Chem. Soc. Perkin Trans. 2001, 1, 2638-2643;
5. b) Sanghvi, Y.S. personal communication.
6. Horvath, I.T.; Rabai, J. Facile catalyst separation without water: Fluorous biphase hydroformylation of olefins. Science 1994, 266, 72-75.
7. Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P., Wipf, P.; Curran, D.P. Fluorous synthesis: A fluorous-phase strategy for improving separation efficiency in organic synthesis. Science 1997, 275, 823-826.
8. Horvath, I.T. Fluorous biphase chemistry. Accounts Chem. Res. 1998, 31, 641-650.
9. Betzemeier, B.; Knochel, P. Palladium-catalyzed cross-coupling of organozinc bromides with aryl iodides in perfluorinated solvents. Angewandte Chemie 1997, 36, 2623-2624.
10. Wende, M.; Meier, R.; Gladysz, J.A. Fluorous catalysis without fluorous solvents: A friendlier catalyst recovery/recycling protocol based upon thermomorphic properties and liquid/solid phase separation. J. Am. Chem. Soc. 2001, 123, 11490-11491.
11. Bonora, G.M.; Scremin, C.L.; Colonna, F.P.; Garbesi, A. HELP (high efficiency liquid phase) new oligonucleotide synthesis on soluble polymeric support. Nucleic Acids Res. 1990, 18, 3155-3159.
12. Gravert, D.J.; Janda, K.D. Organic synthesis on soluble polymer supports: Liquid-phase methodologies. Chem. Rev. 1997, 97, 489-509.
13. Toy, P.H.; Janda, K.D. Soluble polymer-supported organic synthesis. Accounts Chem. Res. 2000, 33, 546-554.
14. Donga, R.A.; Khaliq-Uz-Zaman, S.M.; Chan, T.-H.; Damha, M.J. A novel approach to oligonucleotide synthesis using an imidazolium ion tag as a soluble support. J. Org. Chem. 2006, 71, 7907-7910.
15. Law, M.C.; Wong, K.-Y.; Chan, T.H. Solvent-free route to ionic liquid precursors using a water-moderated microwave process. Green Chemistry 2002, 4, 328-330.
16. Reese, C.B.; Serafinowska, H.T.; Zappia, G. An acetal group suitable for the protection of 2′-hydroxy functions in rapid oligoribonucleotide synthesis. Tetrahedron Lett. 1986, 27, 2291-2294.
17. Kierzek, R.; Ito, H.; Bhatt, R.; Itakura, K. Selective N-deacylation of N,O-protected nucleosides by zinc bromide. Tetrahedron Lett. 1981, 22, 3761-3764.
18. Hayakawa, Y.; Uchiyama, M.; Noyori, R. Nonaqueous oxidation of nucleoside phosphites to phosphates. Tetrahedron Lett. 1986, 27, 4191-4194.