PPN Pyrophosphate: A New Reagent for the Preparation of Nucleoside Triphosphates

Korhonen, Heidi; Bolt, Hannah L.; Vicente-Gines, Leyre; Perks, Daniel C.; Hodgson, David R. W.

doi:10.1080/10426507.2014.984032

Cited by 9 publications

(13 citation statements)

References 23 publications

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“…This process is not suitable for modified nucleosides and in addition involves difficult purification processes due to the presence of secondary products. A recent contribution to this strategy (Korhonen et al, 2015 ) propose the use of tris{bis(triphenylphosphoranylidene) ammonium} (PPN) pyrophosphate as an alternative to the hygroscopic alkylammonium salts.…”

Section: Modified Nucleoside Triphosphate Synthesismentioning

confidence: 99%

Modified Nucleoside Triphosphates for In-vitro Selection Techniques

2016

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The development of SELEX (Selective Enhancement of Ligands by Exponential Enrichment) provides a powerful tool for the search of functional oligonucleotides with the ability to bind ligands with high affinity and selectivity (aptamers) and for the discovery of nucleic acid sequences with diverse enzymatic activities (ribozymes and DNAzymes). This technique has been extensively applied to the selection of natural DNA or RNA molecules but, in order to improve chemical and structural diversity as well as for particular applications where further chemical or biological stability is necessary, the extension of this strategy to modified oligonucleotides is desirable. Taking into account these needs, this review intends to collect the research carried out during the past years, focusing mainly on the use of modified nucleotides in SELEX and the development of mutant enzymes for broadening nucleoside triphosphates acceptance. In addition, comments regarding the synthesis of modified nucleoside triphosphate will be briefly discussed.

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Section: Modified Nucleoside Triphosphate Synthesismentioning

confidence: 99%

Modified Nucleoside Triphosphates for In-vitro Selection Techniques

2016

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“…PPN pyrophosphate was prepared as described previously [ 11 ] and was dried in a vacuum desiccator over P 2 O 5 (we have also found freeze-drying to be effective in other experiments), then dissolved in dry acetonitrile, and stored over activated 4 Å molecular sieves. Tosylated nucleoside 1a–d (0.18 mmol) and PPN pyrophosphate (0.36 mmol) in dry acetonitrile (0.8 mL) were stirred at 30 °C under an inert atmosphere.…”

Section: Methodsmentioning

confidence: 99%

“…Synthetic approaches towards nucleoside-5'-phosphates are well-established [ 4 ], however, the methods tend to be cumbersome. Newer approaches have started to become available over the last decade, where a key driver in these approaches is limiting the effects of moisture on the reaction outcome [ 5 – 11 ].…”

Section: Introductionmentioning

confidence: 99%

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A procedure for the preparation and isolation of nucleoside-5’-diphosphates

Korhonen¹,

Bolt²,

Hodgson³

2015

Beilstein J. Org. Chem.

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“…+ salt of hydrogenpyrophosphate15 (Scheme 1).The protonation reactions proceed cleanly, and all metaphosphate acids synthesized via this method can be isolated by precipitating the products from the reaction mixture or by crystallization. [PPN] 2 [P 3 O 9 H] (2) was synthesized via protonation of [PPN] 3 [P 3 O 9 ] with TFA in acetonitrile (MeCN).…”

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confidence: 99%

Crystalline Metaphosphate Acid Salts: Synthesis in Organic Media, Structures, Hydrogen-Bonding Capability, and Implication of Superacidity

et al. 2016

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Metaphosphate acids cannot be thoroughly studied in aqueous media because their acidity is leveled by the solvent, and the resulting metaphosphates are susceptible to acid-catalyzed hydrolysis. Exploration of metaphosphate acid chemistry has now been made possible with the development of a general synthetic method for organic media soluble metaphosphate acids. Protonation of the [PPN](+) salts ([PPN](+) = [N(PPh3)2](+)) of tri-, tetra-, and hexametaphosphates results in five new metaphosphate acids, [PPN]2[P3O9H] (2), [PPN]4[(P4O12)3H8] (3), [PPN]4[P6O18H2]·2H2O (4), [PPN]3[P6O18H3] (5), and [PPN]2[P6O18H2(H3O)2] (6), obtained in yields of 80, 71, 66, 88, and 76%, respectively. Additionally, our synthetic method can be extended to pyrophosphate to produce [PPN][P2O7H3] (7) in 77% yield. The structural configurations of these oxoacids are dictated by strong hydrogen bonds and the anticooperative effect. Intramolecular hydrogen bonds are observed in 2, 4, and 5 and the previously reported [PPN]2[P4O12H2] (1), while intermolecular hydrogen bonds are observed in 3, 6, and 7. The hydrogen bonds in 3-7 possess short distances and are classified as low-barrier hydrogen bonds. Gas-phase acidity computations reveal that the parent tri- and tetrametaphosphoric acids are superacids. Their remarkable acidity is attributable to the stabilization of their corresponding conjugate bases via intramolecular hydrogen bonding.

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PPN Pyrophosphate: A New Reagent for the Preparation of Nucleoside Triphosphates

Cited by 9 publications

References 23 publications

Modified Nucleoside Triphosphates for In-vitro Selection Techniques

Modified Nucleoside Triphosphates for In-vitro Selection Techniques

A procedure for the preparation and isolation of nucleoside-5’-diphosphates

Crystalline Metaphosphate Acid Salts: Synthesis in Organic Media, Structures, Hydrogen-Bonding Capability, and Implication of Superacidity

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