4'-desmethyl nucleoside analog compounds

Details 4'-desmethyl nucleoside analog compounds 4'-desmethyl nucleoside analog compounds

1990-08-13

1993-06-29

Brown, Johnnie R.

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

Organic compounds

Chalcogen bonded directly to ring carbon of the purine ring...

544242, 544245, 544264, 544277, 544311, 544314, 544317, 536 2714, 536 2854, C07D47300

Patent

active

052236188

ABSTRACT:
Novel oligonucleotide analogs are provided having improved cellular uptake, improved resistance to nucleases, and good hybridization to target RNA. Such analogs are provided having substantially non-chiral, non-ionic linking functionalities between the sugars and sugar analogs thereof. In accordance with preferred embodiments, the 4' position of a sugar or sugar analog at one nucleoside is linked to the 3' position of a second sugar or sugar analog of a second nucleoside by a linking function that comprises a two- or three- carbon backbone chain. In accordance with preferred embodiments, the linking functions comprise the formula)--R.sub.1 --O where R.sub.1 comprises a two or three carbon backbone. Such linking functions also, preferably comprise ether functionalities to effect such linkage. Processes for the automated synthesis of oligonucleotide analogs are also provided.

REFERENCES:
patent: 4591614 (1986-05-01), Miller et al.
C. R. Johnson, et al., Tetrahedron Letters, 28, 4131-4134, (1987).
A. K. Biggadike, et al., Journal Chemical Society, Chemical Communication, 458 (1990).
T. Atkinson and M. Smith (Oligonucleotide Synthesis. A Practical Approach. M. J. Gait, Ed., IRL Press, Washington, D.C., 1985, p. 49).
M. Matteucci, Deoxyoligonucleotide Analogs Based On Formacetal Linkages. Tetrahedron Letters, vol. 31, 17:2385-2388, 1990.
J. M. Coull, D. V. Carlson and H. L. Weith. Synthesis And Characterization Of A Carbamate-Linked Oligonucleoside. Tetrahedron Letters, vol. 28, pp. 745-748.
E. P. Stirchak et al., Uncharged Stereoregular Nucleic Acid Analogues. 1. Synthesis of a Cytosine-Containing Ogligomer with Carbamate Internucleoside Linkages. J. Org. Chem., vol. 52 pp. 4202-4206, 1987.

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