Non-nucleoside linkers for convenient attachment of labels to oligonucleotides using standard synthetic methods

作者: Kuei-Ying Lin , Mark Matteucci

DOI:

关键词:

摘要: Pseudonucleosides and pseudonucleotides are useful in the synthesis of oligomers which contain these components as a means to derivatize resulting oligonucleotide substituents such chelators, intercalators, or lipophilic compounds. In general, pseudonucleotide formula: ##STR1## wherein each Y is independently O S; X H, PO 3 -2 , an activated nucleotide coupling moiety, protecting group, nucleoside, sequence, comprises solid support; F functional group capable linking additional moiety said already reacted effect binding moiety; □ organic backbone does not Y-X either achiral even when different, single enantiomer chiral compound; with proviso that at least one nucleotide, support, represents group. Oligonucleotides having pseudonucleoside 3' terminus particularly stable vivo.

参考文章(31)
Robert L. Letsinger, Cholesteryl modified oligonucleotides ,(1989)
Bruce C. Baguley, Gordon W. Rewcastle, William A. Denny, Graham J. Atwell, Substituted o-phenylenediamine acridine compounds having antitumor activity ,(1983)
Thomas Horn, Michael S. Urdea, Method for making nucleic acid probes ,(1988)
R L Letsinger, G R Zhang, D K Sun, T Ikeuchi, P S Sarin, Cholesteryl-conjugated oligonucleotides: synthesis, properties, and activity as inhibitors of replication of human immunodeficiency virus in cell culture Proceedings of the National Academy of Sciences of the United States of America. ,vol. 86, pp. 6553- 6556 ,(1989) , 10.1073/PNAS.86.17.6553
R. L. Letsinger, S. A. Bach, J. S. Eadie, Effects of pendant groups at phosphorus on binding properties of d-ApA analogues Nucleic Acids Research. ,vol. 14, pp. 3487- 3499 ,(1986) , 10.1093/NAR/14.8.3487
Mark Matteucci, Deoxyoligonucleotide analogs based on formacetal linkages Tetrahedron Letters. ,vol. 31, pp. 2385- 2388 ,(1990) , 10.1016/S0040-4039(00)97368-4
Paul S. Nelson, Rivka Sherman-Gold, Roy Leon, A new and versatile reagent for incorporating multiple primary aliphatic amines into synthetic oligonucleotides Nucleic Acids Research. ,vol. 17, pp. 7179- 7186 ,(1989) , 10.1093/NAR/17.18.7179
Sudhir Agrawal, John Goodchild, Oligodeoxynucleoside methylphosphonates: synthesis and enzymic degradation Tetrahedron Letters. ,vol. 28, pp. 3539- 3542 ,(1987) , 10.1016/S0040-4039(00)95529-1