Monomers for preparation of oligonucleotides having chiral phosp

Details Monomers for preparation of oligonucleotides having chiral phosp Monomers for preparation of oligonucleotides having chiral phosp

1991-10-15

1993-05-18

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 268, 536 2533, C07H 1904, C07H 1906, C07H 1915

Patent

active

052122956

ABSTRACT:
Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN.sub.2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3' position of a xylonucleotide. The reaction proceeds via inversion at the 3' position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

REFERENCES:
patent: 3336289 (1967-08-01), Wechter et al.
patent: 3687808 (1972-08-01), Merrigan et al.
patent: 3792039 (1974-02-01), Erickson et al.
patent: 3846402 (1974-11-01), Eckstein et al.
patent: 4310662 (1982-01-01), Crea
patent: 4500707 (1985-02-01), Caruthers et al.
patent: 4591614 (1986-05-01), Miller et al.
patent: 4663446 (1987-05-01), Wright
Van Pelt et al., J. Biol. Chem., 261(34), 15995-15999 (1986).
Lee et al., Biochemistry, 24(3), 551-555 (1985).
Richard et al., J. Am. Chem. Soc., 105(22), 6605-6609 (1983).
Jarvest et al., J. Chem. Soc. Chem. Comm., 1979, 364-365.
Tsai, Biochemistry, 19,(23), 5310-5316 (1980).
Sammons et al., J. Biol. Chem., 257(3), 1138-1141 (1982).
Lesnikowski et al., Nucl. Acids Res., 18(8), 2109-2115 (1990).
Sopchik et al., Tett. Lett., 30(10), 1221-1224 (1989).
Guga et al., Tett. Lett., 25(7), 2897-2900 (1984).
Stec et al.(I), Tett. Lett., 26(18), 2191-2194 (1985).
Stec. et al.(II), J. Org. Chem., 50(20), 3908-3913 (1985).
Miller, P. S., McParland, K. B., Jayaraman, K., and Ts'o, P.O.P. (1981), Biochemistry, 20:1874.
Koole, L. H., van Genderen, M. H. P., Reiners, R. G., and Buck, H. M. (1987), Proc. K. Ned Adad. Wet., 90:41.
Letsinger, R. L., Bach, S. A., and Eadie, J. S. (1986), Nucleic Acids Res., 14:3487.
Jager, A., Levy, M. J., and Hecht, S. M. (1988), Biochemistry, 27:7237.
Bryant, F. R. and Benkovic, S. J. (1979), Biochemistry, 18:2825.
Niewiarowski, et al. (1987) Acta Biochimica Polonia, 34:217.
Fujii, M., Ozaki, K., Sekine, M. and Hata, T. (1987), Tetrahedron, 43:3395.
Stec, W. J., Zon, G., and Uznanski, B. (1985), J. Chromatography, 325:263.
J. Goodchild (1990) Bioconjugate Chemistry, 1:165.
Burgers, P. M. J. and Eckstein, F. (1979), J. Biological Chemistry, 254:6889.
Gupta, A., DeBrosse, C., and Benkovic, S. J. (1982) J. Bio. Chem., 256:7689.
Brody, R. S. and Frey, P. S. (1981), Biochemistry, 20:1245.
Eckstein, F. and Jovin, T. M. (1983) Biochemistry, 2:4546.
Brody, R. S., Adler, S., Modrich, P., Stec, W. J., Leznikowski, Z. J. and Frey, P. A. (1982) Biochemistry, 21:2570-2572.
Romaniuk, P. J. and Eckstein, F. (1982) J. Biol. Chem., 257:7684-7688.
Burgers, P. M. J. and Eckstein, F. (1978) Proc. Natl. Acad. Sci., USA, 75: 4798-4800.
Cruse W. B. T., Salisbury T., Brown, T., Cosstick, R., Eckstein, F., and Kennard O. (1986), J. Mol. Biol., 192:891.
Ueda T., Tohda, H., Chikazuni, N., Eckstein, R., and Wantanabe K. (1991) Nucleic Acids Research, 19:547.
Antisense Olognucleotides: A New Therapeutic Principle, Uhlmann, E. and Peyman, A. (1990), Chemical Reviews, 90:543.
Suzaki, S., Yamazaki, A., Kamimura, A., Mitsugi, K., and Kumashior, I. (1970), Chem. Pharm. Bull. (Tokyo), 18:172.
Holy, A. and Sorm, F. (1969), Coll. Czech. Chem. Commun., 34:1929.
Hubert-Habart, M. and Goodman, L. (1969) Chem. Commun., 740.
Holy A. (1967) Coll. Czech. Chem. Commun, 32:3713.
Eckstein, F. (1966 & 1970), J. Am. Chem. Soc., 88:4292 & 92:4718.
Murray, A. W. and Atkinson, J. R. (1968), Biochemistry, 7:4023.
Szarek, W. A., Ritchie, R. G. S., and Vyas, D. M. (1978), Carbohydr. Res., 62:89.
Lee, et al. (1971), J. Med. Chem., 14:819.
Mizuno, Y., Knaeko, C., Oikawa, Y. Ikeda, T., and Itoh, T. (1972), J. Am. Chem. Soc., 94:4737.
Daluge, S. and Vince, R. (1972), J. Med. Chem., 15:171.
Miller N. and Fox J. J. (1964), J. Org. Chem., 29:1772.
Letters R. and Michelson, A. M. (1961), J. Chem. Soc., 1410.
Doerr, I. L. and Fox J. J. (1967), J. Am. Chem. Soc., 89:1760.
Ikehara, M. and Kaneko, M. (1970), Tetrahedron, 26:4251.
Mizuno, Y., Kaneko, C., and Oikawa Y. (1974), J. Org. Chem., 39:1440.
Marumoto, R. and Honjo, M. (1974), Chem. Pharm. Bull., 22:128.
Haga, K., Yoshikawa, M., and Kato, T. (1970), Bull Chem. Soc. Jpn., 43:3922-3924.
Robins, M. J., Fouron, Y., and Mengel, R. (1974), J. Org. Chem, 39:1564.
Kondo, K., Adachi, T., and Inoue, I. (1977), J. Org. Chem., 42:3967.
Schuman, D., Robins, J. J. and Robin, R. K. (1970), J. Am. Chem. Soc., 92:3434.
Reist, E. J., Bartuska, V. J., Calkins, D. F. and Goodman, L. (1965), J. Org. Chem., 30:3401.

Affiliated with

Also associated with

Rating

Monomers for preparation of oligonucleotides having chiral phosp does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Monomers for preparation of oligonucleotides having chiral phosp, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Monomers for preparation of oligonucleotides having chiral phosp will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-805404