Efficient solid-phase synthesis of oligodeoxynucleotides having a 5′-terminal 2,2,7-trimethylguanosine pyrophosphate linkage

Ohkubo, Akihiro; Sasaki, Kenji; Noma, Yasuhiro; Tsunoda, Hirosuke; Seio, Kohji; Sekine, Mitsuo

doi:10.1016/j.bmc.2009.04.073

Cited by 9 publications

(6 citation statements)

References 14 publications

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“…Since pyrophosphate formation is easier than triphosphate formation, this route resulted in higher coupling yields. Whether this RNA is still biologically active remains to be demonstrated [ 113 ]. Furthermore, these capping approaches can be used to produce biologically relevant RNA.…”

Section: Reviewmentioning

confidence: 99%

Synthetic mRNA capping

Muttach¹,

Muthmann²,

Rentmeister³

2017

Beilstein J. Org. Chem.

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Eukaryotic mRNA with its 5′-cap is of central importance for the cell. Many studies involving mRNA require reliable preparation and modification of 5′-capped RNAs. Depending on the length of the desired capped RNA, chemical or enzymatic preparation – or a combination of both – can be advantageous. We review state-of-the art methods and give directions for choosing the appropriate approach. We also discuss the preparation and properties of mRNAs with non-natural caps providing novel features such as improved stability or enhanced translational efficiency.

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Section: Reviewmentioning

confidence: 99%

Synthetic mRNA capping

Muttach¹,

Muthmann²,

Rentmeister³

2017

Beilstein J. Org. Chem.

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“…An improvement in solution synthesis of capped oligomers has been proposed by using a 4,4 0 -dimethoxytrityl (DMT) group as a lipophilic purification handle, which facilitates separation of capped RNAs from uncapped RNAs by RP HPLC [113]. Solid-phase synthesis of capped oligonucleotides has been attempted as well, but found to be challenging due to incompatibility of the m 7 G moiety with standard oligonucleotide de-immobilization and de-protection protocols [114][115][116][117][118]. Combination of RNA capping via these approaches with phosphate modifications appears even more challenging and remains to be demonstrated.…”

Section: Phosphate Modifications For Chemical Capping Approachesmentioning

confidence: 99%

Applications of Phosphate Modification and Labeling to Study (m)RNA Caps

Warmiński

Sikorski

Kowalska

et al. 2017

Phosphate Labeling and Sensing in Chemical Biology

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The cap is a natural modification present at the 5 0 ends of eukaryotic messenger RNA (mRNA), which because of its unique structural features, mediates essential biological functions during the process of gene expression. The core structural feature of the mRNA cap is an N7-methylguanosine moiety linked by a 5 0 -5 0 triphosphate chain to the first transcribed nucleotide. Interestingly, other RNA 5 0 end modifications structurally and functionally resembling the m 7 G cap have been discovered in different RNA types and in different organisms. All these structures contain the 'inverted' 5 0 -5 0 oligophosphate bridge, which is necessary for interaction with specific proteins and also serves as a cleavage site for phosphohydrolases regulating RNA turnover. Therefore, cap analogs containing oligophosphate chain modifications or carrying spectroscopic labels attached to phosphate moieties serve as attractive molecular tools for studies on RNA metabolism and modification of natural RNA properties. Here, we review chemical, enzymatic, and chemoenzymatic approaches that enable preparation of modified cap structures and RNAs carrying such structures, with emphasis on phosphate-modified mRNA cap analogs and their potential applications.M. Warminski and P. J. Sikorski have contributed equally to this work.

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“…After deprotection of the 2-cyanoethyl, sulfonylethyl, and N -acyl groups, the 5′-terminal capping reaction was performed by treating residue 6 with m 3 2,2,7 G phosphorimidazolide unit 7 . 11 The 2′-TBDMS groups of the oligomer were subsequently deprotected, and the oligomer was released from the resin by treatment with 1 M tetrabutylammonium fluoride (TBAF) in the presence of 0.5 M AcOH for 24 h. Although the only 2′-TBDMS groups of pseudouridine residues could not be cleaved under the deprotection conditions using TBAF, the TBDMS groups were easily removed by treatment with a 20% acetic acid aqueous solution for 3 h. 12 The target 5′-short RNA I was isolated by anion-exchange HPLC in 2% yield and characterized by MALDI-TOF mass spectrometry. Additionally, the 5′-short RNA II having a pyrophosphate group was obtained as a byproduct in 3% isolated yield.…”

mentioning

confidence: 99%

“…The 5′-terminal pyrophosphate bond was formed by the reaction of the protected oligonucleotide immobilized on the resin with compound 2 for 15 min, as shown in Scheme . After deprotection of the 2-cyanoethyl, sulfonylethyl, and N -acyl groups, the 5′-terminal capping reaction was performed by treating residue 6 with m 3 2,2,7 G phosphorimidazolide unit 7 . The 2′-TBDMS groups of the oligomer were subsequently deprotected, and the oligomer was released from the resin by treatment with 1 M tetrabutylammonium fluoride (TBAF) in the presence of 0.5 M AcOH for 24 h. Although the only 2′-TBDMS groups of pseudouridine residues could not be cleaved under the deprotection conditions using TBAF, the TBDMS groups were easily removed by treatment with a 20% acetic acid aqueous solution for 3 h .…”

mentioning

confidence: 99%

Chemical Synthesis of U1 snRNA Derivatives

et al. 2013

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U1 snRNA is an interesting biological tool for splicing correction and regulation of gene expression. However, U1 snRNA has never been chemically synthesized. In this study, the first chemical synthesis of U1snRNA and its analogues was carried out. Moreover, it was found that the binding affinity of the modified U1 snRNA with an ethylene glycol linkage to snurportin 1 (nuclear import adaptor) was as high as that of the unmodified RNA.

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Efficient solid-phase synthesis of oligodeoxynucleotides having a 5′-terminal 2,2,7-trimethylguanosine pyrophosphate linkage

Cited by 9 publications

References 14 publications

Synthetic mRNA capping

Synthetic mRNA capping

Applications of Phosphate Modification and Labeling to Study (m)RNA Caps

Chemical Synthesis of U1 snRNA Derivatives

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