Uranyl Ion as a Highly Effective Catalyst for Internucleotide Bond Formation

Sawai, Hiroaki; Kuroda, Kensei; Hojo, T

doi:10.1246/bcsj.62.2018

Cited by 74 publications

(37 citation statements)

References 22 publications

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“…The uranyl ion is another very efficient catalyst in aqueous solution, leading to the synthesis of oligomers up to at least 16mers. These oligonucleotide products are predominantly 2 -5 -linked (Sawai et al, 1989(Sawai et al, , 1992. James Ferris and his coworkers have investigated in considerable detail a remarkable series of reactions in which an abundant clay mineral, montmorillonite, catalyzes the synthesis of long oligonucleotides from relatively dilute solutions of nucleoside phosphoramidates including the 5 phosphorimidazolides .…”

Section: Polymerization Of Activated Nucleotidesmentioning

confidence: 99%

Prebiotic Chemistry and the Origin of the RNA World

Orgel

2004

Critical Reviews in Biochemistry and Molecular Biology

907

248

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The demonstration that ribosomal peptide synthesis is a ribozyme-catalyzed reaction makes it almost certain that there was once an RNA World. The central problem for origin-of-life studies, therefore, is to understand how a protein-free RNA World became established on the primitive Earth. We first review the literature on the prebiotic synthesis of the nucleotides, the nonenzymatic synthesis and copying of polynucleotides, and the selection of ribozyme catalysts of a kind that might have facilitated polynucleotide replication. This leads to a brief outline of the Molecular Biologists' Dream, an optimistic scenario for the origin of the RNA World. In the second part of the review we point out the many unresolved problems presented by the Molecular Biologists' Dream. This in turn leads to a discussion of genetic systems simpler than RNA that might have "invented" RNA. Finally, we review studies of prebiotic membrane formation.

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Section: Polymerization Of Activated Nucleotidesmentioning

confidence: 99%

Prebiotic Chemistry and the Origin of the RNA World

Orgel

2004

Critical Reviews in Biochemistry and Molecular Biology

907

248

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“…The uranyl-ion catalyzes oligomerization of natural type ␤-ImpA very efficiently, yielding oligoriboadenylates up to the hexadecamer bearing mainly 2Ј-5Ј linkage (Sawai et al 1989). On the other hand, no long-chained oligoribonucleotide was obtained from ␣-ImpA.…”

Section: Resultsmentioning

confidence: 99%

“…␣-Adenosine 5Ј-phosphorimidazolide was prepared from ␣-adenosine 5Ј-phosphate and imidazole in a similar method to that of ␤-adenosine 5Ј-phosphorimidazolide (Lohrmann and Orgel 1978;Sawai et al 1989). In brief, ␣-adenosine 5Ј-phosphate (12,500 ODU at 260 nm, 0.82 mmol) was dried over phosphorous pentoxide under vacuum.…”

Section: Methodsmentioning

confidence: 99%

An Approach to Prebiotic Synthesis of α-Oligoribonucleotides and Description of Their Properties: Selective Advantage of β-RNA over α-RNA

et al. 1997

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Oligomerization of alpha-adenosine 5'-phosphorimidazolide (alpha-ImpA) has been done in an aqueous solution using a uranyl-ion catalyst or a poly(U) template as a model process of prebiotic synthesis of RNA with alpha-glycosidic linkage. alpha-Oligoriboadenylates up to hexamer were formed from alpha-ImpA by the uranyl-ion catalyst. 3'-5' Linkage was mainly formed in the oligomerization. The poly(U) template mediated the oligomerization of alpha-ImpA, but to a very low extent. The yield and chain length of the resulting alpha-oligomers were far lower than those of the corresponding beta-oligomer formation under the same conditions. Physico-chemical properties of alpha-oligoriboadenylates are presented along with those of the corresponding beta-oligoriboadenylates. The results indicate that beta-RNA is more advantageous than alpha-RNA from the points of their synthesis and properties.

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“…21 5Ј-Phosphoryl 2Ј,5Ј oligoadenylates (pApA, pApApA, and pApApApA) were prepared by uranyl ion catalyzed polymerization of ImpA according to the published method. 24 Snake venom phosphodiesterase and alkaline phosphatase were procured from Worthington Biochemicals, and RNase T2 was purchased from Sigma. DEAE-Sephadex A-25 and Sephadex G-25 were provided by Pharmacia.…”

Section: Methodsmentioning

confidence: 99%

Conformational properties of 2′,5′ linked Rp‐ and Sp‐phosphorothioate oligoadenylates studied by circular dichroism and NMR

et al. 2002

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2Ј,5Ј-Linked oligoadenylates (2-5A) are involved in the antiviral action of interferon. The 2-5A binds and activates 2-5A dependent RNase (RNase L), which degrades viral mRNA, resulting in the inhibition of protein synthesis. 2Ј,5Ј-Linked phosphorothioate oligoadenylates with an Rp configuration bind to and activate the RNase L. On the other hand, 2Ј,5Ј phosphorothioate oligoadenylate with an Sp configuration weakly binds to the RNase L and is devoid of the RNase L activation ability. Comparative circular dichroism (CD) and NMR studies are carried out to characterize the difference in properties between the two configurations of the 2Ј,5Ј phosphorothioate oligoadenylates. 2Ј,5Ј Rp-Phosphorothioate oligoadenylates showed CD spectra similar to those of the corresponding native 2Ј,5Ј oligoadenylates, while the 2Ј,5Ј Sp-phosphorothioate oligoadenylates exhibited a weaker CD band compared to the former two, indicating the weaker base-stacking interaction of the 2Ј,5Ј Sp-phosphorothioate oligoadenylates. The temperature-dependent change in the CD revealed that 2Ј,5Ј phosphorothioate oligoadenylates showed larger ⌬H°and ⌬S°values for the thermal transition of the conformation than the corresponding native 2Ј,5Ј oligoadenylates. The NMR spectral assignment was accomplished by several NMR measuring techniques. The 2Ј-H of the ribose ring linked to the 2Ј,5Ј Sp-phosphorothioate showed a higher field chemical shift of the proton NMR than that linked to the corresponding 2Ј,5Ј Rp-phosphorothioate. 2Ј,5Ј Rp-and Sp-phosphorothioate oligoadenylates possess a sugar conformation similar to that of the corresponding native 2Ј,5Ј oligoadenylates.

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Uranyl Ion as a Highly Effective Catalyst for Internucleotide Bond Formation

Cited by 74 publications

References 22 publications

Prebiotic Chemistry and the Origin of the RNA World

Prebiotic Chemistry and the Origin of the RNA World

An Approach to Prebiotic Synthesis of α-Oligoribonucleotides and Description of Their Properties: Selective Advantage of β-RNA over α-RNA

Conformational properties of 2′,5′ linked Rp‐ and Sp‐phosphorothioate oligoadenylates studied by circular dichroism and NMR

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