Recent Progress in Oligoribonucleotide Synthesis

Pfister, Magdalena; Farkas, Silke; Charubala, Ramamurthy; Pfleiderer, Wolfgang

doi:10.1080/07328318808056292

Cited by 7 publications

(5 citation statements)

References 6 publications

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“…This protection allowed the isolation of UpU in 80% yield. 249 It has also been shown by Pfister and Pfleiderer that the NPES group can serve as a 3'-OH protecting group in the synthesis of (2'-*5')-oligoribonucleotides. 250b…”

Section: Npeoc: P-nitrophenylethyloxy©arbonylmentioning

confidence: 99%

Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach

Beaucage¹,

Iyer²

1992

Tetrahedron

697

390

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Section: Npeoc: P-nitrophenylethyloxy©arbonylmentioning

confidence: 99%

Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach

Beaucage¹,

Iyer²

1992

Tetrahedron

697

390

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“…There are a number of factors to be considered. (1) Pfister et al, 1988Van Aerschot et al, 1988Engels & Mag, 1982Krecmerová et al, 1990 G Nyilas et al, 1988MacMillan & Verdine, 1991Jones et al, 1981Reese & Skone, 1984Jones et al, 1981Reese & Skone, 1984Scalfi-Happ et al, 1987Rao et al, 1987Reese & Skone, 1984Rao et al, 1987Hagen & Chládek, 1989Hagen & Chládek, 1989Engels & Mag, 1982 As noted before, when using the phosphotriester method in oligonucleotide synthesis, O 6 -modified guanine and O 4 -modified uracil revert to guanine and uracil residues upon "oximate" treatment that follows the chain assembly. (2) When the phosphoramidite method is used, O 6 -phosphitylated deoxyguanosine reverts to deoxyguanosine on contact with water or acetate ions (Mag & Engels, 1988).…”

Section: Protection Of Imide and Lactam Functionsmentioning

confidence: 91%

“…Allyloxycarbonyl protecting groups (Hayakawa, Kato, Uchiyama, Kajino, & Noyori, ; Hayakawa, Wakabayashi, Kato, & Noyori, ; Hyodo, & Hayakawa, ) have also been introduced and can be chemoselectively removed under neutral [using Pd(0)] or mildly basic conditions. However, the p ‐nitrophenylethyl (NPE) and ( p ‐nitrophenyl)ethoxycarbonyl (NPEOC) groups (Pfleiderer et al, ; Pfleiderer, ; Pfister, Farkas, Charubala, & Pfleiderer, ; Schirmeister & Pfleiderer, ; Trichtinger et al, ) and the 2‐dansylethoxy cabonyl group (Wagner & Pfleiderer, ) are selectively removed using DBU following a β ‐elimination nucleobase protection strategy. The NPE/NPEOC β ‐elimination nucleobse‐protection strategy in conjunction with a succinyl linker has been used for the preparation of oligonucleotide arrays and high‐quality primers (Weiler & Hoheisel, ) by solid‐phase synthesis.…”

Section: Protection Of Purine Nucleobases: the Problem Of Depurinationmentioning

confidence: 99%

Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Meher

Iyer

2017

CP Nucleic Acid Chemistry

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Oligonucleotides carrying a variety of chemical modifications including conjugates are finding increasing applications in therapeutics, diagnostics, functional genomics, proteomics, and as research tools in chemical and molecular biology. The successful synthesis of oligonucleotides primarily depends on the use of appropriately protected nucleoside building blocks including the exocyclic amino groups of the nucleobases, the hydroxyl groups at the 2'-, 3'-, and 5'-positions of the sugar moieties, and the internucleotide phospho-linkage. This unit is a thoroughly revised update of the previously published version and describes the recent development of various protecting groups that facilitate reliable oligonucleotide synthesis. In addition, various protecting groups for the imide/lactam function of thymine/uracil and guanine, respectively, are described to prevent irreversible nucleobase modifications that may occur in the presence of reagents used in oligonucleotide synthesis. © 2017 by John Wiley & Sons, Inc.

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“…The p-nitrophenylethyl sulfonyl group (S.24) has also been proposed as a 2′-protecting group for ribonucleosides (Pfister et al, 1988). The advantages of this sulfonate-derived group are acid stability and the absence of (2′→3′) migration.…”

Section: The P-nitrophenylethyl Sulfonyl Groupmentioning

confidence: 99%

Strategies for Oligoribonucleotide Synthesis According to the Phosphoramidite Method

Wincott¹

2000

CP Nucleic Acid Chemistry

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Advances in oligoribonucleotide synthesis have lagged behind those in oligodeoxyribonucleotide synthesis because of the difficulty in identifying orthogonal protecting groups for the 2'- and 5'-hydroxyls. Adaptation of the phosphoramidite method for DNA synthesis to RNA synthesis has greatly improved our understanding of RNA. It allows site-specific introduction of modified nucleosides to any position in an RNA molecule, as well as introduction of variations at multiple sites in the molecule. This overview discusses issues that are relevant to RNA synthesis by the phosphoramidite approach, including supports used, activation of the ribonucleoside phosphoramidites, and protection of the nucleobase, phosphate, and 2'- and 5'-hydroxyls.

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Recent Progress in Oligoribonucleotide Synthesis

Cited by 7 publications

References 6 publications

Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach

Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach

Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Strategies for Oligoribonucleotide Synthesis According to the Phosphoramidite Method

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