4,5-Dicyanoimidazole-promoted synthesis of dinucleoside polyphosphates and their analogs

Sun, Qi; Gong, Shan‐Shan; Liu, Si; Sun, Jian; Liu, Guodong; Ma, Chao

doi:10.1016/j.tet.2014.05.013

Cited by 17 publications

(18 citation statements)

References 39 publications

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“…Compared to the conventional phosphoromorpholidate method, this approach afforded products in shorter reaction time and higher isolated yields. 75 A one-pot method for DCI-promoted synthesis of symmetrical NppCX 2 ppN bisphosphonate analogues simply from nucleoside 5´-phosphoropiperidates without using nucleoside phosphonates has also been described. 76 A very effective synthetic procedure for the preparation of a series of dinucleoside tetraphosphate analogues via activated bisphosphonates and nucleoside monophosphates was developed by Yanachkov et al 77 They found that organic salts of pyrophosphoric acid and its halomethylenebisphosphonate analogues react with an excess of 1,1‫-׳‬carbonyldiimidazole (CDI) to give stable, isolable diimidazolidates 77, and that these diimidazolidates react with nucleoside 5´-monophosphates or monothiophosphate 78 to give the corresponding nucleotide analogues 79 conveniently and in high yield (Scheme 31).…”

Section: Scheme 28 Methods For Synthesis Of Nucleoside 5'-phosphoropimentioning

confidence: 99%

Phosphonate analogues of nucleoside polyphosphates

Romanenko¹,

Kukhar²,

Zhdankin³

2017

Arkivoc

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This article provides an overview of the efforts toward the synthesis of nucleoside polyphosphate mimics featuring a P-CXY-P scaffold. The following synthetic approaches to these compounds are summarized: (i) nucleophilic displacement of 5´-O-tosyl nucleoside by the ammonium salts of methylenebisphosphonic acid; (ii) synthesis via activated phosphate/phosphonate substrates; (iii) Mitsunobu coupling between a nucleoside and methylenebisphosphonic acid; (iv) phosphorylation of a protected nucleoside under Yoshikawa's reaction conditions with methylenebis(phosphonic dichloride); (v) synthesis via nucleophilic cleavage of cyclic trimetaphosph(on)ates; (vi) enzyme-mediated reactions.

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Section: Scheme 28 Methods For Synthesis Of Nucleoside 5'-phosphoropimentioning

confidence: 99%

Phosphonate analogues of nucleoside polyphosphates

Romanenko¹,

Kukhar²,

Zhdankin³

2017

Arkivoc

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“…Inosine 5′-phosphoropiperidate was prepared according to known procedures [16]. All reactions were performed under an atmosphere of dry argon.…”

Section: Methodsmentioning

confidence: 99%

“…However, these methods are typically low yielding, and the products are difficult to isolate in high purity. More recently, we developed an efficient method for the synthesis of dinucleoside polyphosphates from the nucleoside phosphoropiperidate precursors [16]. In this paper, we report a one-pot and practical method for the synthesis of diinosine polyphosphates (Ip3I and Ip4I) without using inosine polyphosphates.…”

Section: Introductionmentioning

confidence: 99%

One-pot Synthesis of Diinosine Triphosphate and Tetraphosphate

Huang¹,

Gong²

2016

Proceedings of the 2016 International Conference on Biomedical and Biological Engineering

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“…More recently, application of more‐effective catalysts, such as tetrazole and 4,5‐dicyanoimidazole (DCI), resulted in symmetrical and asymmetrical dinucleoside polyphosphates and nucleoside 5′‐triphosphates 13 (Scheme ), starting from nucleotide piperidates 21 (X=C) in reasonable yields (40–80 %) after 6–30 h . Phosphoramidates 21 were prepared from protected H ‐phosphonate precursors and deblocked before further application .…”

Section: The Use Of Compounds Containing P−n Bondsmentioning

confidence: 99%

“…studied the roles of a number of catalysts in the reaction (Scheme ) and proposed a strategy for P V −N bond activation . Optimized reaction conditions, depending on the cost and solubility of the reactants, were also developed . Ravalico et al.…”

Section: The Use Of Compounds Containing P−n Bondsmentioning

confidence: 99%

How To Form a Phosphate Anhydride Linkage in Nucleotide Derivatives

Sherstyuk

Abramova

2015

ChemBioChem

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The fundamental roles of nucleoside triphosphates and nucleotide cofactors such as NAD(+) in biochemistry are well known. In recent decades, continuing research has revealed the key role of 5'-capped RNA and 5',5'-dinucleoside polyphosphates in the regulation of vitally important physiological processes. Last but not least, the commercial potential of nucleoside triphosphate synthesis can hardly be overestimated. Nevertheless, despite decades of investigation and the obvious topicality of the research on the chemical synthesis of the nucleotide compounds containing phosphate anhydride linkages, none of the existing procedures can be considered an up-to-date "gold standard". However, there are a number of fruitful synthetic approaches to forming phosphate anhydride linkages in satisfactory yield. These are summarized in this concise review, organized by the type of active phosphorous intermediate and reagents used.

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4,5-Dicyanoimidazole-promoted synthesis of dinucleoside polyphosphates and their analogs

Cited by 17 publications

References 39 publications

Phosphonate analogues of nucleoside polyphosphates

Phosphonate analogues of nucleoside polyphosphates

One-pot Synthesis of Diinosine Triphosphate and Tetraphosphate

How To Form a Phosphate Anhydride Linkage in Nucleotide Derivatives

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