Ethynyl, 2-Propynyl, and 3-Butynyl C-Phosphonate Analogues of Nucleoside Di- and Triphosphates: Synthesis and Reactivity in CuAAC

Wanat, Przemysław; Walczak, Sylwia; Wojtczak, Błażej A.; Nowakowska, Monika; Jemielity, Jacek; Kowalska, Joanna

doi:10.1021/acs.orglett.5b01346

Cited by 28 publications

(27 citation statements)

References 23 publications

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“…Fluorescently labeled nucleotide probes were synthesized by performing the CuAAC reaction between nucleotide analogues functionalized at the terminal phosphate moiety with an alkyne handle and various fluorescent tags containing an azide group (Scheme ). Reactions were carried out in dimethyl sulfoxide (DMSO)/H 2 O solutions (with a ratio dependent on the solubility of the fluorescent tag) under standard catalytic conditions (copper(II) sulfate and sodium ascorbate).…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

Kasprzyk

Starek

Ciechanowicz

et al. 2019

Chemistry A European J

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The m 7 Gc ap is au nique nucleotide structure at the 5'-end of all eukaryotic mRNAs. The cap specificallyinteracts with numerous cellular proteins and participates in biological processes that are essential for cell growth and function. To provide small molecularp robest os tudy important cap-recognizing proteins, we synthesized m 7 Gn ucleotides labeled with fluorescent tags via the terminal phosph(on)ate group and studied how their emission properties changed upon protein binding or enzymaticc leavage. Only the pyrene-labeled compounds behaved as sensitive turn-on probes. Ap yrene-labeled m 7 GTP analogue showed up to eightfold enhanced fluorescencee mission upon binding to eukaryotic translation initiation factor 4E (eIF4E) and over 30-folde nhancementu pon cleavageb yd ecapping scavenger (DcpS) enzyme. These observations serveda st he basis for developing binding-and hydrolytic-activity assays. The assay utility was validated with previously characterizedl ibraries of eIF4E ligands and DcpS inhibitors. The DcpS assay was also appliedtostudy hydrolytic activity and inhibition of endogenous enzyme in cytoplasmic extracts from HeLa and HEK cells.

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Section: Resultsmentioning

confidence: 99%

Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

Kasprzyk

Starek

Ciechanowicz

et al. 2019

Chemistry A European J

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“…3 and Table S2†). Alkyne-containing C -phosphonate analogues ( 10a–d , 11a–d , 12a–f ) were obtained by MgCl 2 -mediated coupling between triethylammonium salts of C -phosphonate subunits ( 18a–c ) and guanosine mono- or diphosphate imidazolides ( 19a–b ), 31 followed by N 7 -methylation by methyl iodide (Fig. 3A).…”

Section: Resultsmentioning

confidence: 99%

A novel route for preparing 5′ cap mimics and capped RNAs: phosphate-modified cap analogues obtained via click chemistry

et al. 2017

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“…The mechanism of dealkylation with bromotrimethylsilane, that produces a bis-silylated phosphonate intermediate, thus incited to use tris(trimethylsilyl) phosphite as nucleophilic phosphorus species to produce after methanolysis phosphonic acid [ 166 ] or hydroxymethylene bis-phosphonic acid as illustrated in Fig. 16 with the synthesis of the hydroxymethylenebisphosphonic acid 45 [ 167 ].…”

Section: Reviewmentioning

confidence: 99%

Phosphonic acid: preparation and applications

Sevrain¹,

Berchel²,

Couthon³

et al. 2017

Beilstein J. Org. Chem.

147

103

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The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the synthesis of phosphonic acids a determinant question for numerous research projects. This review gives, first, an overview of the different fields of application of phosphonic acids that are illustrated with studies mainly selected over the last 20 years. Further, this review reports the different methods that can be used for the synthesis of phosphonic acids from dialkyl or diaryl phosphonate, from dichlorophosphine or dichlorophosphine oxide, from phosphonodiamide, or by oxidation of phosphinic acid. Direct methods that make use of phosphorous acid (H3PO3) and that produce a phosphonic acid functional group simultaneously to the formation of the P–C bond, are also surveyed. Among all these methods, the dealkylation of dialkyl phosphonates under either acidic conditions (HCl) or using the McKenna procedure (a two-step reaction that makes use of bromotrimethylsilane followed by methanolysis) constitute the best methods to prepare phosphonic acids.

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Ethynyl, 2-Propynyl, and 3-Butynyl C-Phosphonate Analogues of Nucleoside Di- and Triphosphates: Synthesis and Reactivity in CuAAC

Cited by 28 publications

References 23 publications

Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

A novel route for preparing 5′ cap mimics and capped RNAs: phosphate-modified cap analogues obtained via click chemistry

Phosphonic acid: preparation and applications

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