Preparation of 5′‐Silyl‐2′‐Orthoester Ribonucleosides for Use in Oligoribonucleotide Synthesis
dc.contributor.author | Scaringe, Stephen A. | |
dc.contributor.author | Kitchen, David | |
dc.contributor.author | Kaiser, Robert J. | |
dc.contributor.author | Marshall, William S. | |
dc.date.accessioned | 2020-01-13T15:04:27Z | |
dc.date.available | 2020-01-13T15:04:27Z | |
dc.date.issued | 2004-03 | |
dc.identifier.citation | Scaringe, Stephen A.; Kitchen, David; Kaiser, Robert J.; Marshall, William S. (2004). "Preparation of 5′‐Silyl‐2′‐Orthoester Ribonucleosides for Use in Oligoribonucleotide Synthesis." Current Protocols in Nucleic Acid Chemistry 16(1): 2.10.1-2.10.16. | |
dc.identifier.issn | 1934-9270 | |
dc.identifier.issn | 1934-9289 | |
dc.identifier.uri | https://hdl.handle.net/2027.42/152550 | |
dc.description.abstract | The recent discovery that small interfering RNAs (siRNAs) induce gene suppression in mammalian cells has sparked tremendous interest in using siRNA‐based assays and high‐throughput screens to study gene function. As a result, research programs at leading academic and commercial institutions have become a substantial and rapidly growing market for synthetic RNA. Important considerations in synthesizing RNA for biological gene function studies are sequence integrity, purity, scalability, and resistance to nucleases; ease of chemical modification, deprotection, and handling; and cost. Of the well‐established RNA synthesis methods, 2′‐ACE chemistry is the only one that meets all of these criteria. 2′‐ACE technology employs a unique class of silyl ethers to protect the 5′‐hydroxyl, in combination with an acid‐labile orthoester protecting group on the 2′‐hydroxyl (2′‐ACE). 2′‐ACE‐protected phosphoramidite monomers are joined using standard solid‐phase technology to achieve RNA synthesis at efficiencies rivaling those for DNA. This unit describes the synthesis of standard 5′‐silyl‐2′‐ACE‐protected phosphoramidites. | |
dc.publisher | Wiley Periodicals, Inc. | |
dc.subject.other | ribonucleoside | |
dc.subject.other | phosphoramidite | |
dc.subject.other | RNA synthesis | |
dc.subject.other | orthoester | |
dc.subject.other | silyl protection | |
dc.title | Preparation of 5′‐Silyl‐2′‐Orthoester Ribonucleosides for Use in Oligoribonucleotide Synthesis | |
dc.type | Article | |
dc.rights.robots | IndexNoFollow | |
dc.subject.hlbsecondlevel | Biological Chemistry | |
dc.subject.hlbsecondlevel | Chemical Engineering | |
dc.subject.hlbsecondlevel | Chemistry | |
dc.subject.hlbsecondlevel | Public Health | |
dc.subject.hlbtoplevel | Science | |
dc.subject.hlbtoplevel | Engineering | |
dc.subject.hlbtoplevel | Health Sciences | |
dc.description.peerreviewed | Peer Reviewed | |
dc.description.bitstreamurl | https://deepblue.lib.umich.edu/bitstream/2027.42/152550/1/cpnc0210.pdf | |
dc.identifier.doi | 10.1002/0471142700.nc0210s16 | |
dc.identifier.source | Current Protocols in Nucleic Acid Chemistry | |
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dc.identifier.citedreference | Elbashir, S.M., Harborth, J., Lendeckel, W., Yalcin, A., Weber, K., and Tuschl, T. 2001. Duplexes of 21‐nucleotide RNAs mediate RNA interference in cultured mammalian cells. Nature 411: 494 ‐ 498. | |
dc.identifier.citedreference | Matteucci, M.D. and Caruthers, M.H. 1981. Synthesis of deoxyoligonucleotides on a polymer support. J. Am. Chem. Soc. 103: 3185 ‐ 3191. | |
dc.identifier.citedreference | Scaringe, S.A., Wincott, F.E., and Caruthers, M.H. 1998. Novel RNA synthesis method using 5′‐silyl‐2′‐orthoester protecting groups. J. Am. Chem. Soc. 120: 11820 ‐ 11821. | |
dc.identifier.citedreference | Usman, N.O., Ogilvie, K.K., Jiang, M.Y., and Cedergren, R.J. 1987. The automated chemical synthesis of long oligoribonucleotides using 2′‐ O ‐silylated ribonucleoside 3′‐ O ‐phosphoramidites on a controlled‐pore glass support: Synthesis of a 43‐nucleotide sequence similar to the 3′‐half molecule of an Escherichia coli formylmethionine tRNA. J. Am. Chem. Soc. 109: 7845 ‐ 7854. | |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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