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Literature DB >> 2726485

Prevention of chain cleavage in the chemical synthesis of 2'-silylated oligoribonucleotides.

Abstract

Strong aqueous ammonium hydroxide used to remove N-acyl protecting groups from synthetic oligoribonucleotides causes removal of some alkylsilyl protecting groups from 2'-hydroxyls and leads to chain cleavage. This problem is most severe when 30% ammonium hydroxide is used and substantially reduced but still detectable when 3:1 ammonium hydroxide-ethanol is used. We have virtually eliminated this unwanted cleavage by incorporating the labile phenoxyacetyl amino protecting group on adenosine and guanosine. The N-benzoyl protecting group remains adequate for cytidine nucleosides. Synthetic oligoribonucleotides containing these N-acylated nucleosides and 2'-t-butyldimethylsilyl or 2'-triisopropylsilyl protecting groups can be deacylated by room temperature treatment in saturated anhydrous methanolic ammonia (8-12 h) without causing any detectable chain cleavage.

Entities: Chemical

Mesh：

Substances：

Year: 1989 PMID： 2726485 PMCID： PMC317792 DOI： 10.1093/nar/17.9.3501

Source DB: PubMed Journal: Nucleic Acids Res ISSN： 0305-1048 Impact factor: 16.971

6 in total

1. Synthesis of oligoribonucleotides.

Authors: K K Ogilvie; N Theriault; K L Sadana
Journal: J Am Chem Soc Date: 1977-11-09 Impact factor: 15.419

Review 2. Synthesis and use of synthetic oligonucleotides.

Authors: K Itakura; J J Rossi; R B Wallace
Journal: Annu Rev Biochem Date: 1984 Impact factor: 23.643

3. The chemical synthesis of oligoribonucleotides VII. A comparison of condensing agents in the coupling of silylated ribonucleosides.

Authors: K K Ogilvie; R T Pon
Journal: Nucleic Acids Res Date: 1980-05-10 Impact factor: 16.971

4. Studies on the t-butyldimethylsilyl group as 2'-O-protection in oligoribonucleotide synthesis via the H-phosphonate approach.

Authors: J Stawinski; R Strömberg; M Thelin; E Westman
Journal: Nucleic Acids Res Date: 1988-10-11 Impact factor: 16.971

5. Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity.

Authors: K K Ogilvie; N Usman; K Nicoghosian; R J Cedergren
Journal: Proc Natl Acad Sci U S A Date: 1988-08 Impact factor: 11.205

6. The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups.

Authors: J C Schulhof; D Molko; R Teoule
Journal: Nucleic Acids Res Date: 1987-01-26 Impact factor: 16.971

6 in total

23 in total

1. Hydroquinone-O,O'-diacetic acid ('Q-linker') as a replacement for succinyl and oxalyl linker arms in solid phase oligonucleotide synthesis.

Authors: R T Pon; S Yu
Journal: Nucleic Acids Res Date: 1997-09-15 Impact factor: 16.971

2. Chemical synthesis of biologically active oligoribonucleotides using beta-cyanoethyl protected ribonucleoside phosphoramidites.

Authors: S A Scaringe; C Francklyn; N Usman
Journal: Nucleic Acids Res Date: 1990-09-25 Impact factor: 16.971

Prevention of chain cleavage in the chemical synthesis of 2'-silylated oligoribonucleotides.

1. Synthesis of oligoribonucleotides.

Review 2. Synthesis and use of synthetic oligonucleotides.

3. The chemical synthesis of oligoribonucleotides VII. A comparison of condensing agents in the coupling of silylated ribonucleosides.

4. Studies on the t-butyldimethylsilyl group as 2'-O-protection in oligoribonucleotide synthesis via the H-phosphonate approach.

5. Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity.

6. The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups.

1. Hydroquinone-O,O'-diacetic acid ('Q-linker') as a replacement for succinyl and oxalyl linker arms in solid phase oligonucleotide synthesis.

2. Chemical synthesis of biologically active oligoribonucleotides using beta-cyanoethyl protected ribonucleoside phosphoramidites.

3. Synthesis of cyclic oligodeoxyribonucleotides via the 'filtration' approach.

4. Identification of a high-affinity RNA-binding site for the human immunodeficiency virus type 1 Rev protein.

5. Synthesis of oligonucleotides containing 2'-deoxy-6-thioguanosine at a predetermined site.

6. Coaxial stacking of helixes enhances binding of oligoribonucleotides and improves predictions of RNA folding.

7. Different conformational families of pyrimidine.purine.pyrimidine triple helices depending on backbone composition.

8. Activity of hammerhead ribozymes containing non-nucleotidic linkers.

9. TAR-RNA binding by HIV-1 Tat protein is selectively inhibited by its L-enantiomer.

10. Chemical synthesis of a biologically active natural tRNA with its minor bases.