Improved chemistry for the production of synthetic oligodeoxyribonucleotides

Antisense and Nucleic Acid Drug Development

Volumn 9, Issue 4, 1999, Pages 361-366

  Wilk, Andrzej ^a   Grajkowski, Andrzej ^a   Srinivasachar, Kasturi ^a   Beaucage, Serge L ^a  

^a CENTER FOR BIOLOGICS EVALUATION AND RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001172473     PISSN: 10872906     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

1. BARONE, A.D., TANG, J.-Y., and CARUTHERS, M.H. (1984). In situ activation of bis-dialkylaminophosphines-A new method for synthesizing deoxyoligonucleotides on polymer supports. Nucleic Acids Res. 12,4051061.
2. BEAUCAGE, S.L., and IYER, R.P. (1992). Advances in the synthesis of oligonucleotides by the phosphoramidite approach. Tetrahedron 48,2223-2311.
3. BOAL, J.H., WILK, A., HARFNDRANATH, N., MAX, E.E., KEMPE, T., and BEAUCAGE, S.L. (1996). Cleavage of oligodeoxyribonucleotides from controlled-pore glass supports and their rapid deprotection by gaseous amines. Nucleic Acids Res. 24, 3115-3117.
4. CHAMBERS, R.W. (1965). The chemistry of pseudouridine. IV. Cyanoethylation. Biochemistry 4,219-226.
5. CRIPPA, S., DI GENNARO, P., LUCINI, R., ORLANDI, M., and RINDONE, B. (1993). Characterization of adducts of nucleic bases and acrylic monomers. Gazz. Chem. Ital. 123,197-203.
6. LEE, H.-J., and MOON, S.-H. (1984). Bis-(N,N-dialkylamino)alkoxyphosphines as a new class of phosphite coupling agent for the synthesis of oligonucleotides. Chem. Lett. 1229-1232.
7. MAG, M., and ENGELS, J.W. (1988). Synthesis and structure assignments of amide protected nucleosides and their use as phosphoramidites in deoxyoligonucleotide synthesis. Nucleic Acids Res. 16, 3525-3543.
8. MILLER, P.S. (1996). Antisense/antigene oligonucleotides. In: Bioorganic Chemistry: Nucleic Acids. S.M. Hecht, ed. (Oxford University Press, New York), pp. 347-374.
9. OGILVIE, K.K., and BEAUCAGE, S.L. (1979). Fluoride ion promoted deprotection and transesterification in nucleotide triesters. Nucleic Acids Res. 7, 805-823.
10. PROKOPCZYK, B., BERTINATO, P., and HOFFMAN, D. (1988). Synthesis and kinetics of decomposition of 7-(2-cyanoethyl)guanine and O6-(2-cyanoethyl)guanine, markers for reaction of acrylonitrile and 3-(methylnitrosoamino)propionitrile with DNA. Carcinogenesis 9,2125-2128.
11. REDDY, M.P., HANNA, N.B., and FAROOQUI, F. (1994). Fast cleavage and deprotection of oligonucleotides. Tetrahedron Lett. 35, 4311-4314.
12. SOLOMON, J.J., COTE, I.L., WORTMAN, M., DECKER, K., and SEGAL, A. (1984). In vitro alkylation of calf thymus DNA by acrylonitrile. Isolation of cyanoethyl-adducts of guanine and thymidine and carboxyethyl-adducts of adenine and cytosine. Chem. Biol. Interact. 51,167-190.
13. TENER, G.M. (1961). 2-Cyanoethyl phosphate and its use in the synthesis of phosphate esters. J. Am. Chem. Soc. 83, 159-168.
14. THOMAS, T., and THOMAS, T.J. (1993). Selectivity of polyamines in triplex DNA stabilization. Biochjmistry 32,14068-14074.
15. WEBER, H., and KHORANA, H.G. (1972). CIV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxynucleotide corresponding to the nucleotide sequence 21 to 40. J. Mol. Biol. 72,219-249.
16. WILK, A., SRINIVASACHAR, K., and BEAUCAGE, S.L. (1997). NTrifluoroacetylamino alcohols as phosphodiester protecting groups in the synthesis of oligodeoxyribonucleotides. J. Org. Chem. 62, 6712-6713.
17. YAMANA, K., N1SHIJIMA, Y., OKA, A., NAKANO, H., SANGEN, O., OZAKI, H., and SHIMIDZU, T. (1989). A simple preparation of 5'-O-dimethoxytrityl deoxyribonucleoside 3'-O-phosphorbisdiethylamidites as useful intermediates in the synthesis of oligodeoxyribonucleotides and their phosphorodiethylamidate analogs on a solid support. Tetrahedron 45,4135-4140.