Protected nucleosides which permit more efficient oligonucleotid

Details Protected nucleosides which permit more efficient oligonucleotid Protected nucleosides which permit more efficient oligonucleotid

1987-03-30

1990-12-25

Rollins, John W.

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

Organic compounds

Carbohydrates or derivatives

536 26, 536 27, 536 28, 536 29, 536 24, C07H 19067, C07H 19073, C07H 19167, C07H 19173

Patent

active

049804600

ABSTRACT:
The invention relates to derivatives of nucleosides and their use for the synthesis of oligonucleotides.
These derivatives are in accordance with the formula: ##STR1## in which B represents a radical derived from guanine, cytosine or adenine, whose exocylic NH group is protected by the group ##STR2## with R.sup.1 representing a hydrogen atom or an alkyl radical and R.sup.2 a hydrogen atom, and alkyl radical, an alkoxy radical and optionally substituted aryloxy radical, R.sup.3 represents a hydrogen atom, the dimethoxytrityl radical or the radical ##STR3## R.sup.4 represents a hydrogen atom, the radical of formula: ##STR4## or a radical suitable for the synthesis of polynucleotides and R.sup.5 represents a hydrogen atom or the protected or unprotected hydroxyl OH radical.

REFERENCES:
patent: 4500707 (1985-02-01), Caruthers et al.
Nucleic Acids Research, (1987), vol. 15, pp. 397-416 "The Final Deprotection Step in Oligonucleotide Synthesis is Reduced to a Mild and Rapid Ammonia Treatment by Using Labile Base-Protecting Groups", J. C. Schulhof, et al.
Methods in Enzymology, (1980), vol. 65, pp. 499-560, "Sequencing End-Labeled DNA with Base-Specific Chemical Cleavages", A. M. Maxam et al.
Kochetkov et al., "Org. Chem. of Nucleic Acids, Part A", Plenum Press, New York, 1971, pp. 64-67.
Hall et al, J. Chem. Soc., pp. 3291-3296, 1957.
Kame et al., J. Org. Chem., pp. 2139-2143.
Kosten et al., Tetrahedron, vol. 37, pp. 363-369, 1981.

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