Oligonucleotides containing hydroxyl-protecting groups orthogona

Details Oligonucleotides containing hydroxyl-protecting groups orthogona Oligonucleotides containing hydroxyl-protecting groups orthogona

1995-04-13

1997-12-30

Wilson, James O.

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

Organic compounds

Carbohydrates or derivatives

536 221, 536 243, 536 2431, 536 2432, 536 253, 536 2534, 536 255, 536 268, 536 2761, 536 2763, 536 285, 536 2851, 536 2852, 435 6, C07H 2100

Patent

active

057032181

ABSTRACT:
Hydroxyl-protecting groups orthogonally removable by reduction with a liquid reducing agent are disclosed. The novel hydroxyl-protecting groups are particularly useful in the chemical synthesis of linear and branched oligonucleotide structures, as they are readily removed from the protected molecule with mild reagents such as dithionite. Examples of such hydroxyl-protecting groups include the 2-methylene-9,10-anthraquinone (Maq) carbonate ester and the p-nitrobenzyl carbonate ester.

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B. Alberts et al., Molecular Biol. Cell (New York: Garland Publishing, 1982), at p. 222.
N. Balgobin et al., "A Novel Strategy for the Chemical Synthesis of DNA and RNA Fragments Using 2-Oxymethyleneanthraquinone (MAQ) as a 3'-Terminal Phosphate Protecting Group," Chemica Scripta 20:198-200 (1982).
R.L. Blankespoor et al., "Electroreductive Cleavage of 2-Methylene-9,10-anthraquinone (MAQ) Esters of Carboxylic Acids and N-Substituted Carbamic Acids: Protecting Groups for Carboxylic Acids and Primary Amines," J. Org. Chem. 49:4441-46 (1984).
D.S. Kemp et al., "New Protective Groups for Peptide Synthesis--III The MAQ Ester Group Mild Reductive Cleavage of 2-Acyloxymethyleneanthraquinones," Tetrahedron Letters 12:1031-1034 (1977).
L. Stryer, Biochemistry (San Francisco: W.H. Freeman and Company, 1981) at p. 597.

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