Iterative Synthesis of Nucleoside Oligophosphates with Phosphoramidites

Cremosnik, Gregor S.; Hofer, Alexandre; Jessen, Henning J.

doi:10.1002/anie.201306265

Cited by 73 publications

(89 citation statements)

References 35 publications

(9 reference statements)

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“…On the basis of their retention times, the products eluting after ADP and ATP were likely to be AP 4 and AP 5 . These two compounds were chemically synthesised by using the P III approach reported by Jessen et al., and were used as reference standards for HPIC analysis. The reference compounds were further analysed analogously to the enzymatically produced samples by HPIC and eluted with retention times identical to those of the enzymatic products (Table S1, Figures S7 and S8).…”

Section: Methodsmentioning

confidence: 99%

Several Polyphosphate Kinase 2 Enzymes Catalyse the Production of Adenosine 5′‐Polyphosphates

et al. 2019

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Polyphosphate kinases (PPKs) are involved in many metabolic processes; enzymes of the second family (PPK2) are responsible for nucleotide synthesis fuelled by the consumption of inorganic polyphosphate. They catalyse the phosphorylation of nucleotides with various numbers of phosphate residues, such as monophosphates or diphosphates. Hence, these enzymes are promising candidates for cofactor regeneration systems. Besides adenosine 5′‐triphosphate, PPK2s also catalyse the synthesis of highly phosphorylated nucleotides in vitro, as shown here for adenosine 5′‐tetraphosphate and adenosine 5′‐pentaphosphate. These unusually phosphorylated adenosine 5′‐polyphosphates add up to 50 % of the whole adenosine nucleotides in the assay. The two new products were chemically synthesised to serve as standards and compared with the two enzymatically produced compounds by high‐performance ion chromatography and 31P NMR analysis. This study shows that PPK2s are highly suitable for biocatalytic synthesis of different phosphorylated nucleotides.

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Section: Methodsmentioning

confidence: 99%

Several Polyphosphate Kinase 2 Enzymes Catalyse the Production of Adenosine 5′‐Polyphosphates

et al. 2019

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“…The introduction of ap hosphate ester at the 5-OH group of d-ribose can be achieved by using phosphoramidite reagents. [27,29] Both types of protecting groups were studied here to establish their suitability. [26][27][28] The Fm groups can be removed, for example, either with triethylamine or with piperidine.…”

Section: Synthesis Of the Asymmetric Phosphoramiditementioning

confidence: 99%

Synthesis of a Bioreversibly Masked Lipophilic Adenosine Diphosphate Ribose Derivative

Pahnke

Meier

2017

ChemBioChem

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The design of a bioreversibly protected lipophilic sugar nucleotide as a potential membrane-permeable precursor of adenosine diphosphate ribose (ADPR) is described. ADPR is the most potent activator of the transient receptor potential melastatin 2 (TRPM2) ion channel. Membrane-permeable, lipophilic derivatives of ADPR are of great interest as tools for study of the mechanism of TRPM2. The approach described here was based on our recently disclosed "DiPPro" and "TriPPPro" prodrug approaches developed for the intracellular delivery of nucleotides. A lipophilic, bioreversibly masked ADPR analogue containing an enzymatically cleavable 4-pentanoyloxybenzyl (PB) mask at the phosphate moiety next to the 5'-position of adenosine, together with O-acetyl groups, was prepared in high yields. Chemical and enzymatic hydrolysis studies in phosphate buffer (pH 7.3) were performed to assess chemical stability and possible (selective) enzymatic demasking of the ADPR analogue. HPLC-MS revealed that the PB group was readily cleaved enzymatically. In addition, the formation of partially deacetylated ADPR compounds and also of fully unprotected ADPR was observed.

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“…1 Over the last ~25-50 years, a small number of key methods have been adopted for the preparation of NTPs and other phosphoanhydrides, 2 although new methods are now becoming available. [3][4][5][6][7][8][9][10][11][12][13][14] Often, these approaches rely on triand tetralkylammonium salts as organic-solvent-soluble sources of nucleophilic phosphate. Unfortunately, these salts are extremely hygroscopic, [15][16][17][18][19][20] with deleterious consequences on the water-sensitive reactions that use them.…”

Section: Introductionmentioning

confidence: 99%

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

Korhonen

Bolt

Vicente-Gines

et al. 2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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Iterative Synthesis of Nucleoside Oligophosphates with Phosphoramidites

Cited by 73 publications

References 35 publications

Several Polyphosphate Kinase 2 Enzymes Catalyse the Production of Adenosine 5′‐Polyphosphates

Several Polyphosphate Kinase 2 Enzymes Catalyse the Production of Adenosine 5′‐Polyphosphates

Synthesis of a Bioreversibly Masked Lipophilic Adenosine Diphosphate Ribose Derivative

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

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