Oligoribonucleotides protecting groups

Protection of primary alcohols. This trityl bromide in the presence of AgNO, m DMF reacts selectively with the primary hydroxyl group of carbohydrates and nucleosides. The CPTr ether group is stable to aqueous pyridine and 80% acetic acid, but is selectively cleaved by hydrazine in pyridine-acetic acid. This protecting group is useful in the synthesis of oligoribonucleotides. 

The deprotection of crude oligoribonucleotides traditionally requires a basic treatment that concomitantly allows transamination of the exocyclic acyl protecting groups, /8-elimination of the 2-cyanoethyl phosphate protecting group, and cleavage of the succinic ester bond that links the oligoribonucleotide to the solid support. The base deprotection is by far the most rate-... 

Capaldi DC, Reese CB. Use of the l-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and related protecting groups in oligoribonucleotide synthesis Stability of intemucleotide linkages to aqueous acid. Nucleic Acids Res 22 2209-2216, 1994. 

Rastogi J, Usher D. A new 2 -hydroxyl protecting group for the automated synthesis of oligoribonucleotides. Nucleic Acids Res 23 4872-4877, 1995. 

Christodoulou C, Agrawal S, Gait MJ. Incompatibility of acid-labile 2 and 5 protecting groups for solid-phase synthesis of oligoribonucleotides. Tetrahedron Lett 27 1521-1522, 1986. 

Beijer B, Sulston I, Sproat BS, Rider P, Lamond AI, Neuner P. Synthesis and applications of oligoribonucleotides with selected 2 -0-methylation using the 2 -0-[l-(2-fluorophenyl)-4-methoxypiperidin-4-yl] protecting group. Nucleic Acids Res 18 5143-5151, 1990. 

Chaix C, Molko D, Teoule R. The use of labile base protecting groups in oligoribonucleotide synthesis. Tetrahedron Lett 30 71-74, 1989. 

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