The Cu2+-Promoted Cleavage of mRNA 5′-capAnalogs: A Kinetic Study with P1-(7-Methylguanosin-5′-yl) P3-(Nucleosid-5′-yl) Triphospates and P1-(7-Methylguanosin-5′-yl) P4-(Guanosin-5′-yl) Tetraphosphate

Wieczorek, Z; Darżynkiewicz, Edward; Kuusela, Satu; Lönnberg, Harri

doi:10.1080/07328319908045590

Cited by 11 publications

(11 citation statements)

References 15 publications

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“…As the size of the bulge is still decreased, the cleavage is even more markedly retarded: the phosphodiester bond within three- (11), two- (12) or one-nucleotide (13) bulges, are even more stable than those at the bulge-stem junction of a five-nucleotide bulge (as in 4 or 8). This is also the case with phosphodiester bonds within the double helical stem (14). With structures 11-14, no reaction could be observed in three months.…”

Section: The Effect Of the Structure On The Inherent Reactivity Of Ph...mentioning

confidence: 73%

“…The chimeric ribo/2Ј-O-methylribooligonucleotides (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were synthesised from commercial 2Ј-O-methylated (Glenn Research) and 2Ј-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl] (2Ј-O-Fpmp) protected (Cruachem) building blocks by a conventional phosphoramidite strategy, according to the standard RNA-coupling protocol of ABI 392 DNA/RNA Synthesizer. The protecting groups were removed and the crude oligonucleotides were purified as described previously.…”

Section: Methodsmentioning

confidence: 99%

“…7 Numerous studies using simple RNA mimics have been carried out to find efficient catalysts for both the cleavage of phosphodiester bonds 1,8-11 and phosphoanhydrides. [12][13][14] In the search for efficient cleaving agents, simple RNA mimetics are generally used as substrates. It is known, however, that as the structure of the substrate becomes more complicated, it starts to affect the reactivity of the phosphodiester Scheme 1 The cleavage of RNA 3Ј,5Ј-phosphodiester bonds by intramolecular transesterification.…”

Section: Introductionmentioning

confidence: 99%

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The cleavage of phosphodiester bonds within small RNA bulges in the presence and absence of metal ion catalysts †

Kaukinen

Bielecki

Mikkola

et al. 2001

J. Chem. Soc., Perkin Trans. 2

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This work studies the effect of RNA structure on the reactivity of RNA phosphodiester bonds. The aim of the study is to evaluate those structural parameters that affect reactivity to support the development of sequence-specific RNA cleaving agents. The cleavage of phosphodiester bonds within one-to five-nucleotide bulges has been studied in buffer solutions (pH 8.4), and in the presence of Zn 2ϩ aqua ion (pH 6.4) or its 1,5,9-triazacyclododecane complex (pH 7.4). Molecular modelling has been applied to study the structure of the substrates. The basis of the reactivity and the catalytic potential of metal ion-based cleaving agents are discussed.

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Section: The Effect Of the Structure On The Inherent Reactivity Of Ph...mentioning

confidence: 73%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The cleavage of phosphodiester bonds within small RNA bulges in the presence and absence of metal ion catalysts †

Kaukinen

Bielecki

Mikkola

et al. 2001

J. Chem. Soc., Perkin Trans. 2

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“…This can be achieved with an electron-withdrawing carbonyl group adjacent to the triple bond. 8 The advantage of having an activated triple bond donor as a linker appeared even more important when developing a methodology for clicking of the m 3 G-CAPs as cap structures can, at least partially, decompose in the presence of copper ions, 23,24 if conditions are too harsch.…”

Section: Resultsmentioning

confidence: 99%

Capping of oligonucleotides with “clickable” m3G-CAPs

et al. 2012

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The RNA components of small nuclear ribonucleoproteins (U snRNPs) possess a characteristic 59-terminal 2,2,7-trimethyl-guanosine CAP structure (m 3 G-CAP). This cap is an important component of the nuclear localization signal of U snRNPs. Here we report synthesis of four m 3 G-CAP constructs and the effective attachment of these onto oligonucleotides (ONs) using Cu(I) [3 + 2] cycloaddition (''click chemistry''). The four constructs (1-4, Fig. 1) are equipped with a handle that in principle allows for universal conjugation to any cargo and differ in their complexity starting from m 3 GpppA (linker) to m 3 GpppA (OMe) U (OMe) A (linker) that resembles the native m 3 G-CAP followed by the 29-O-methylated sequence AUA. The four m 3 G-CAP containing constructs are equipped with an azide linker and by taking advantage of initial attachment of a novel activated triple bond donor p-aminomethyltoluic acid (PATA) to ONs on solid support we were able to synthesize novel bioconjugates equipped with different constructs carrying the m 3 G-CAP Nuclear Localisation Signal (NLS) for the investigation of nuclear delivery.

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“…chemical agents that sequenceselectively cleave RNA molecules. The metal ion promoted hydrolytic reactions have been studied in more detail [15][16][17][18][19][20][21][22][23][24][25][26][27][28]. One aim of these works has been functional modelling of natural enzymes cleaving phosphoric anhydride bridges.…”

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confidence: 99%

Hydrolysis of dinucleoside phosphates – mRNA 5′ cap analogues – promoted by a binuclear copper(II)–zinc(II) complex

Szilágyi

Mikkola

Lönnberg

et al. 2007

Journal of Inorganic Biochemistry

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The Cu²⁺-Promoted Cleavage of mRNA 5′-capAnalogs: A Kinetic Study with P¹-(7-Methylguanosin-5′-yl) P³-(Nucleosid-5′-yl) Triphospates and P¹-(7-Methylguanosin-5′-yl) P⁴-(Guanosin-5′-yl) Tetraphosphate

Cited by 11 publications

References 15 publications

The cleavage of phosphodiester bonds within small RNA bulges in the presence and absence of metal ion catalysts †

The cleavage of phosphodiester bonds within small RNA bulges in the presence and absence of metal ion catalysts †

Capping of oligonucleotides with “clickable” m3G-CAPs

Hydrolysis of dinucleoside phosphates – mRNA 5′ cap analogues – promoted by a binuclear copper(II)–zinc(II) complex

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