A Safe and Practical Procedure for Global Deprotection of Oligoribonucleotides
We report a practical global deprotection of RNA 2′-O-tert-butyldimethylsilyl (TBS) ethers using commercially available aqueous NH4F. The procedure is applicable to both 96-well plate format and large-scale production of RNA. This improved procedure provides a safe, mild, and cost-effective alternat...
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| Published in | Journal of organic chemistry Vol. 75; no. 15; pp. 5305 - 5307 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
06.08.2010
Amer Chemical Soc |
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| Abstract | We report a practical global deprotection of RNA 2′-O-tert-butyldimethylsilyl (TBS) ethers using commercially available aqueous NH4F. The procedure is applicable to both 96-well plate format and large-scale production of RNA. This improved procedure provides a safe, mild, and cost-effective alternative to highly hazardous Et3N·3HF, a reagent commonly used in the routine synthesis of RNA. |
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| AbstractList | We report a practical global deprotection of RNA 2′-O-tert-butyldimethylsilyl (TBS) ethers using commercially available aqueous NH4F. The procedure is applicable to both 96-well plate format and large-scale production of RNA. This improved procedure provides a safe, mild, and cost-effective alternative to highly hazardous Et3N·3HF, a reagent commonly used in the routine synthesis of RNA. We report a practical global deprotection of RNA 2'-O-tert-butyldimethylsilyl (TBS) ethers using commercially available aqueous NH(4)F. The procedure is applicable to both 96-well plate format and large-scale production of RNA. This improved procedure provides a safe, mild, and cost-effective alternative to highly hazardous Et(3)N x 3 HF, a reagent commonly used in the routine synthesis of RNA. We report a practical global deprotection of RNA 2'-O-tert-butyldimethylsilyl (TBS) ethers using commercially available aqueous NH(4)F. The procedure is applicable to both 96-well plate format and large-scale production of RNA. This improved procedure provides a safe, mild, and cost-effective alternative to highly hazardous Et(3)N center dot 3HF, a reagent commonly used in the routine synthesis of RNA. |
| Author | Gosselin, Francis DiMichele, Lisa Cvetovich, Raymond J Zewge, Daniel Sidler, Rick |
| Author_xml | – sequence: 1 givenname: Daniel surname: Zewge fullname: Zewge, Daniel email: daniel_zewge@merck.com – sequence: 2 givenname: Francis surname: Gosselin fullname: Gosselin, Francis – sequence: 3 givenname: Rick surname: Sidler fullname: Sidler, Rick – sequence: 4 givenname: Lisa surname: DiMichele fullname: DiMichele, Lisa – sequence: 5 givenname: Raymond J surname: Cvetovich fullname: Cvetovich, Raymond J |
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| Cites_doi | 10.1021/ja0636587 10.1016/j.cbpa.2004.04.012 10.1039/b809851d 10.1139/V07-022 10.1016/j.jfluchem.2005.09.016 10.1093/nar/22.12.2209 10.1016/S0040-4039(01)95650-3 10.1139/v07-022 10.1016/0040-4039(95)01953-F 10.1021/cr960425x 10.1093/nar/21.20.4739 10.1093/nar/22.12.2430 10.1002/1522-2675(20011219)84:12<3773::AID-HLCA3773>3.0.CO;2-E 10.1021/ja980730v 10.1093/nar/23.14.2677 10.1073/pnas.85.16.5764 10.1093/nar/23.19.3949 10.1016/S0040-4039(00)91889-6 10.1016/0040-4020(96)00364-X 10.1016/S0040-4039(01)91764-2 |
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| Keywords | HYDROXYL FUNCTIONS RNA-SYNTHESIS REMOVAL SOLID-PHASE SYNTHESIS CHEMICAL-SYNTHESIS PROTECTING GROUPS TETRABUTYLAMMONIUM FLUORIDE Chemical reagent Ether RNA Hydrofluoric acid Deprotection Nucleotide Oligoribonucleotide Organic silane Large scale Aqueous solution Chemical synthesis Ammonium fluorides |
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| Snippet | We report a practical global deprotection of RNA 2′-O-tert-butyldimethylsilyl (TBS) ethers using commercially available aqueous NH4F. The procedure is... We report a practical global deprotection of RNA 2'-O-tert-butyldimethylsilyl (TBS) ethers using commercially available aqueous NH(4)F. The procedure is... |
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| SubjectTerms | Analytical, structural and metabolic biochemistry Biological and medical sciences Carbohydrates. Nucleosides and nucleotides Chemistry Chemistry, Organic Chromatography, High Pressure Liquid Exact sciences and technology Fluorides - chemistry Fundamental and applied biological sciences. Psychology Nucleic acids Nucleosides, nucleotides and oligonucleotides Oligoribonucleotides - chemistry Organic chemistry Physical Sciences Preparations and properties Quaternary Ammonium Compounds - chemistry Rna, ribonucleoproteins Science & Technology Spectrometry, Mass, Electrospray Ionization Spectrophotometry, Ultraviolet |
| Title | A Safe and Practical Procedure for Global Deprotection of Oligoribonucleotides |
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