Oligonucleotides with alternating anionic and cationic phosphoramidate linkages: Synthesis and hybridization of stereo-uniform isomers

被引:24
作者
Horn, T [1 ]
Chaturvedi, S [1 ]
Balasubramaniam, TN [1 ]
Letsinger, RL [1 ]
机构
[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208
关键词
D O I
10.1016/0040-4039(95)02309-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An oligonucleotide containing alternating anionic and stereo-uniform cationic dimethylaminopropylphosphoramidate linkages, d(T+T-)(7)T, is shown to bind with unusually high affinity to DNA [poly(dA) and d(C(2)A(15)C(2))] and RNA [poly(rA)] targets in solutions of low ionic strength. The isomeric oligomer with the opposite configuration at the phosphoramidate links binds much less efficiently.
引用
收藏
页码:743 / 746
页数:4
相关论文
共 9 条
  • [1] OLIGONUCLEOTIDES WITH NOVEL, CATIONIC BACKBONE SUBSTITUENTS - AMINOETHYLPHOSPHONATES
    FATHI, R
    HUANG, Q
    COPPOLA, G
    DELANEY, W
    TEASDALE, R
    KRIEG, AM
    COOK, AF
    [J]. NUCLEIC ACIDS RESEARCH, 1994, 22 (24) : 5416 - 5424
  • [2] PHOSPHORAMIDATE ANALOGS OF DNA - SYNTHESIS AND THERMAL-STABILITY OF HETERODUPLEXES
    FROEHLER, B
    NG, P
    MATTEUCCI, M
    [J]. NUCLEIC ACIDS RESEARCH, 1988, 16 (11) : 4831 - 4839
  • [3] ZWITTERIONIC DNA
    HASHIMOTO, H
    NELSON, MG
    SWITZER, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) : 7128 - 7134
  • [4] OLIGONUCLEOTIDE N-ALKYLPHOSPHORAMIDATES - SYNTHESIS AND BINDING TO POLYNUCLEOTIDES
    JAGER, A
    LEVY, MJ
    HECHT, SM
    [J]. BIOCHEMISTRY, 1988, 27 (19) : 7237 - 7246
  • [5] HYBRIDIZATION OF ALTERNATING CATIONIC/ANIONIC OLIGONUCLEOTIDES TO RNA SEGMENTS
    JUNG, PM
    HISTAND, G
    LETSINGER, RL
    [J]. NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (6-7): : 1597 - 1605
  • [6] CATIONIC OLIGONUCLEOTIDES
    LETSINGER, RL
    SINGMAN, CN
    HISTAND, G
    SALUNKHE, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) : 4470 - 4471
  • [7] MILLER PS, 1980, J BIOL CHEM, V255, P9659
  • [8] SYNTHESES AND PROPERTIES OF OLIGOTHYMIDYLATE ANALOGS CONTAINING STEREOREGULATED PHOSPHOROMORPHOLIDATE AND PHOSPHODIESTER LINKAGES IN AN ALTERNATING MANNER
    OZAKI, H
    KITAMURA, M
    YAMANA, K
    MURAKAMI, A
    SHIMIDZU, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (07) : 1929 - 1936
  • [9] SYNTHESIS, BASE-PAIRING PROPERTIES AND NUCLEASE RESISTANCE OF OLIGOTHYMIDYLATE ANALOGS CONTAINING METHOXYPHOSPHORAMIDATE INTERNUCLEOSIDE LINKAGES
    PEYROTTES, S
    VASSEUR, JJ
    IMBACH, JL
    RAYNER, B
    [J]. NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (10): : 2135 - 2149