N.sup.4 - acylated cytidinyl compounds useful in oligonucleotide

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 2851, 536 253, 536 2531, C07H 19073

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054281482

ABSTRACT:
Disclosed herein are protecting groups for exocyclic amino groups of the bases adenine, guanine and cytosine for use in the synthesis of oligonucleotides, the protecting groups being represented by the formula: --CO-- (CH.sub.2).sub.0-9 --CH.sub.3. In a particularly preferred embodiment, the base cytosine is protected with acetyl (--CO--CH.sub.3), and the oligonucleotide incorporating said protected cytosine is subjected to a cleavage/deprotection reagent comprising at least one straight chain alkylamine having from 1 to about 10 carbon atoms.

REFERENCES:
patent: 4415732 (1988-11-01), Caruthers et al.
Chemical Abstracts "File CA" structure searches, completed Mar. 23, 1993.
Stawinski et al., "Studies on the t-Butyldimethylsilyl Group as 2'-O-Protection in Oligoribonucleotide Synthesis Via the H-Phosphonate Approach," Nucleic Acids Res., 16(19), 9285-9298 (1988).
Beardsley et al., "Chemical Synthesis of DNA Oligomers Containing Cytosine Arabinoside," Nucleic Acids Res., 16(19), 9165-9176 (1988).
Bhat, V. et al "A Simple and Convenient Method for the Selective N-Acylatrims of Cytosine Nucleotides"Nucleosides & Nucleotides 8(2): 179-183 (1989).
Chaix, C., et al. "The Use of Labile Base Protecting Groups in Oligonucleotide Synthesis" Tetrahedron Letters 30(1): 71-74 (1989).
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Koster, H. "N-Acyl Protecting Groups for Deoxynucleotides: A Quantitative and Comparative Study" Tetrahedron 37: 363-369 (1981).
Chaix, C., et al. "Solid Phase Synthesis of the 5'-Half of the Initiator t-RNA from B. Subtilis" Nuc. Acid Res. 17(18): 7381-7393 (1989).
Weber H. & Khorana, H. G. "CIV. Total Synthesis of the Structured Gene for an Alanine Transfer Ribonucleic Acid From Yeast" J. Mol. Biol. 72: 219-249 (1972).
Vu, H., et al "Fast Oligonucleotide Deprotection Phosphoramidite Chemistry for DNA Synthesis" Tetrahedron Letters 31(50): 7269-7272 (1990).
Sinha, N. D., et al. "Polymer Support Oligonucleotide Synbthesis XVIII" Nuc. Acids Res. 12(11): 4539-4556 (1984).
McBride, L. J. & Caruthers, M. H. "An Investigation of Several Oligonucleotide Phosphoramidites Useful for Synthesizing Doxyunucleotides" Tetrahedron Letters 24(3): 245-248 (1983).

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