Solid-supported diphosphitylating and triphosphitylating reagents for nucleoside modification

Current Protocols in Nucleic Acid Chemistry

Volumn , Issue SUPPL. 33, 2008, Pages

  Ahmadibeni, Yousef ^a   Parang, Keykavous ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

Diphosphodiester; Diphosphorylation; Modified oligodeoxynucleotides; Nucleosides; Solid phase synthesis; Triphosphorylation

Indexed keywords

4 HYDROXYBENZYL ALCOHOL; 5 HYDROXYMETHYL 2 ACETOXYBENZOIC ACID; ACETYLSALICYLIC ACID; ADENOSINE DIPHOSPHATE; ALCOHOL DERIVATIVE; DIPHOSPHITYLATING REAGENT; N BOC 4 HYDROXYBENZYL ALCOHOL; OLIGODEOXYNUCLEOTIDE; OLIGONUCLEOTIDE; POLYMER; REAGENT; TERT BUTYL HYDROPEROXIDE; THYMIDINE DIPHOSPHATE; TRIPHOSPHITYLATING REAGENT; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE;

CROSS COUPLING REACTION; DNA MODIFICATION; NUCLEOTIDE METABOLISM; OXIDATION; PHOSPHORYLATION; PRIORITY JOURNAL; PROTEIN PURIFICATION; REVIEW; SOLID PHASE SYNTHESIS;

EID: 57349128385     PISSN: 19349270     EISSN: 19349289     Source Type: Journal    
DOI: 10.1002/0471142700.nc1308s33     Document Type: Review

References (25)

1. Ahmadibeni, Y. and Parang, K. 2005. Selective diphosphorylation, dithiodiphosphorylation, triphosphorylation and trithiotriphosphorylation of unprotected carbohydrates and nucleosides. Org. Lett. 7:5589-5592.
2. Ahmadibeni, Y. and Parang, K. 2007. Synthesis and evaluation of oligodeoxynucleotides containing internucleotide diphosphodiester linkages. Angew. Chem. Int. Ed. Engl. 46:4739-4743.
3. Arts, E.J. and Wainberg, M.A. 1996. Mechanisms of nucleoside analog antiviral activity and resistance during human immunodeficiency virus reverse transcription. Antimicrob. Agents Chemother. 40:527-540.
4. -32P-labeled or unlabeled nucleoside 5′-triphosphates and thiamine triphosphate. Anal. Biochem. 322:190-197.
5. Burgess, K. and Cook, D. 2000. Synthesis of nucleoside triphosphates. Chem. Rev. 100:2047-2059.
6. Désaubry, L., Shoshani, I., and Johnson, R.A. 1995. Synthesis of 2′-deoxy- and 2′, 5′-dideoxyadenosine-3′-di- and 3′-triphosphate. Tetrahedron Lett. 36:995-996.
7. Furman, P.A., Fyfe, J.A., St. Clair, M.H., Weinhold, K., Rideout, J.L., Freeman, G.A., Lehrman, S.N., Bolognesi, D.P., Broder, S., Mitsuya, H., and Barry, D.W. 1986. Phosphorylation of 3′-azido-3′-deoxythymidine and selective interaction of the 5′-triphosphate with human immunodeficiency virus reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A. 83:8333-8337.
8. He, K., Hasan, A., Kryzanowska, B., and Shaw, B.R. 1998. Synthesis and separation of diastereomers of ribonucleoside 5′-(α-Pborano) triphosphates. J. Org. Chem. 63:5769-5773.
9. Hovinen, J., Azhayeva, E., Azhayev, A., Gustaev, A., and Lonnberg, H. 1994. Synthesis of 3′-O-(ω-aminoalkyoxymethyl)thymidine 5′-triphosphates, terminators of DNA synthesis that enable 3′-labeling. J. Chem. Soc. Perkin Trans. I 1:211-217.
10. Kaiser, E., Colescott, R.L., Bossinger, C.D., and Cook, P.I. 1970. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34:595-598.
11. Kaur, H., Babu, B.R., and Maiti, S. 2007. Perspectives on chemistry and therapeutic applications of locked nucleic acid (LNA). Chem. Rev. 107:4672-4697.
12. Kumar, A., Ye, G., Ahmadibeni, Y., and Parang, K. 2006. Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: Applications in solid-phase organic synthesis. J. Org. Chem. 71:7915-7918.
13. Matsukura, M., Shinozuka, K., Zon, G., Mitsuya, H., Reitz, M., Cohen, J.S., and Broder, S. 1987. Phosphorothioate analogs of oligodeoxynucleotides: Inhibitors of replication and cytopathic effects of human immunodeficiency virus. Proc. Natl. Acad. Sci. U.S.A. 84:7706-7710.
14. Mofatt, J.G. and Khorana, H.G. 1961. Nucleoside polyphosphates. X. The synthesis and some reactions of nucleoside 5′-phosphoromorpholidates and related compounds. Improved methods for the preparation of nucleoside 5′-polyphosphates. J. Am. Chem. Soc. 83:649-658.
15. Opalinska, J. 2007. Nucleic acid drugs in the clinic. Expert Opin. Drug Dis. 2:321-333.
16. Pensato, S., Saviano, M., and Romanelli, A. 2007. New peptide nucleic acid analogues: Synthesis and applications. Expert Opin. Biol. Ther. 7:1219-1232.
17. Prober, J.M., Trainor, G.L., Dam, R.J., Hobbs, F.W., Robertson, C.W., Zagursky, R.J., Cocuzza, A.J., Hensen, M.A., and Baumeister, K. 1987. A system for rapid DNA sequencing with fluorescent chain-terminating dideoxynucleotides. Science 238:336-341.
18. Sahu, N.K., Shilakari, G., Nayak, A., and Kohli, D.V. 2007. Antisense technology: A selective tool for gene expression regulation and gene targeting. Curr. Pharm. Biotechnol. 8:291-304.
19. Saravolac, E.G. and Wong, J.P. 2007. Recent patents on development of nucleic acid-based antiviral drugs against seasonal and pandemic influenza virus infections. Recent Patents Anti-Infect. Drug Disc. 2:140-147.
20. Shoshani, I., Laux, W.H.G., Perigaud, C., Gosselin, G., and Johnson, R.A. 1999. Inhibition of adenylyl cyclase by acyclic nucleoside phosphonate antiviral agents. J. Biol. Chem. 274:34742-34744.
21. Stein, C.A. and Kreig, A.M. (eds.) 1998. Applied Antisense Oligonucleotide Technology. John Wiley & Sons, New York.
22. Strerath, M., Detmer, I., Gaster, J., and Marx, A. 2007. Modified oligonucleotides as tools for allele-specific amplification. Methods Mol. Biol. 402:317-328.
23. Tor, Y. and Dervan, P.B. 1993. Site-specific enzymatic incorporation of an unnatural base, N6-(6-aminohexyl)isoguanosine, into RNA. J. Am. Chem. Soc. 115:4461-4467.
24. Van Rompay, A.R., Johansson, M., and Karlsson, A. 2000. Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases. Pharmacol. Ther. 87:189-198.
25. Wang, L.C., Lee, J.H., Yang, Y.H., Lin, Y.T., and Chiang, B.L. 2007. New biological approaches in asthma: DNA-based therapy. Curr. Med. Chem. 14:1607-1618.