Physicochemical Aspects of Aqueous and Nonaqueous Approaches to the Preparation of Nucleosides, Nucleotides and Phosphate Ester Mimics

Hodgson, David

doi:10.1016/bs.apoc.2017.09.002

Cited by 8 publications

(12 citation statements)

References 83 publications

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“…Often the extractant is aqueous [2,22], but water/acetonitrile mixtures are in use as well [27][28][29]. The solubility of the analytes in the solvent should be considered when choosing the extractant volume in relation to the sample amount, especially when less soluble Nbs [3] are extracted. If solubility is limiting, re-extraction of a pellet will result again in high analyte concentration in the supernatant.…”

Section: Extraction Of Nts and Ns From Plant Samplesmentioning

confidence: 99%

“…The choice of analytical strategies is naturally determined by the physicochemical properties of NTs and Ns. These are polar compounds and the phosphate group(s) of the NTs deprotonate and carry negative charges (pKa values of about 2) [ 3 ] within a broad range of pH values. NTs and Ns contain primary, secondary, and tertiary amines, which, especially under more acid conditions, can protonate and acquire a positive charge especially under more acidic conditions [ 3 ].…”

Section: Introductionmentioning

confidence: 99%

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Analysis of Nucleosides and Nucleotides in Plants: An Update on Sample Preparation and LC–MS Techniques

Straube

Witte

Herde

2021

Cells

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Nucleotides fulfill many essential functions in plants. Compared to non-plant systems, these hydrophilic metabolites have not been adequately investigated in plants, especially the less abundant nucleotide species such as deoxyribonucleotides and modified or damaged nucleotides. Until recently, this was mainly due to a lack of adequate methods for in-depth analysis of nucleotides and nucleosides in plants. In this review, we focus on the current state-of-the-art of nucleotide analysis in plants with liquid chromatography coupled to mass spectrometry and describe recent major advances. Tissue disruption, quenching, liquid–liquid and solid-phase extraction, chromatographic strategies, and peculiarities of nucleotides and nucleosides in mass spectrometry are covered. We describe how the different steps of the analytical workflow influence each other, highlight the specific challenges of nucleotide analysis, and outline promising future developments. The metabolite matrix of plants is particularly complex. Therefore, it is likely that nucleotide analysis methods that work for plants can be applied to other organisms as well. Although this review focuses on plants, we also discuss advances in nucleotide analysis from non-plant systems to provide an overview of the analytical techniques available for this challenging class of metabolites.

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Section: Extraction Of Nts and Ns From Plant Samplesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Analysis of Nucleosides and Nucleotides in Plants: An Update on Sample Preparation and LC–MS Techniques

Straube

Witte

Herde

2021

Cells

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“…Then, we present the synthetic strategies to obtain dinucleotides. Pyrophosphate bond formation has been addressed in some recent reviews and book chapters [1,[13][14][15]. The current review focuses on methods reported for the synthesis of dinucleoside 5′,5′-polyphosphates, especially those of biological and pharmacological interest.…”

Section: Interaction Of Dnps With Purine and Pyrimidine Receptorsmentioning

confidence: 99%

“…Divalent cations, especially Mg 2+ and Zn 2+ , are sometimes added as catalysts for anhydride bond formation. It is assumed that the metal ion could serve two roles, namely, the activation of the electrophilic P(V) center and templating the incoming phosphate nucleophile and the P(V) electrophilic center [13].…”

Section: Synthesis Based On P(v) Chemistrymentioning

confidence: 99%

“…Interestingly, the study of dinucleotides using NMR techniques ( 1 H, 13 C and 31 P) can determine the conformation (syn/anti, sugar puckering), nucleobase properties (tautomerism, H-bonds and π-stacking interactions), as well as the anomeric α/β configuration. Such data are crucial for understanding the structure-activity relationship of either natural or synthetic dinucleotides as enzyme inhibitors and receptor ligands, and the design of potent therapeutic agents based on a dinucleotide scaffold.…”

Section: Physico-chemical Propertiesmentioning

confidence: 99%

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Synthetic Strategies for Dinucleotides Synthesis

et al. 2019

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Dinucleoside 5′,5′-polyphosphates (DNPs) are endogenous substances that play important intra- and extracellular roles in various biological processes, such as cell proliferation, regulation of enzymes, neurotransmission, platelet disaggregation and modulation of vascular tone. Various methodologies have been developed over the past fifty years to access these compounds, involving enzymatic processes or chemical procedures based either on P(III) or P(V) chemistry. Both solution-phase and solid-support strategies have been developed and are reported here. Recently, green chemistry approaches have emerged, offering attracting alternatives. This review outlines the main synthetic pathways for the preparation of dinucleoside 5′,5′-polyphosphates, focusing on pharmacologically relevant compounds, and highlighting recent advances.

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Ball‐Milling to Access Dinucleoside Polyphosphates and Analogues

Navarro,

Vasco,

Bantreil

et al. 2024

Adv Synth Catal

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Dinucleoside 5’,5’‐polyphosphates (NpnNs) play essential roles in various biological processes. Access to these high value‐added compounds, while avoiding the many drawbacks of solution phase synthesis, is a challenge that has been overcome thanks to mechanochemistry. A straightforward solid‐state synthesis based on activation of phosphate or pyrophosphate sodium salts to their diimidazolides, followed by coupling with commercially available nucleotides, under air conditions, gave symmetrical NpnNs. The scope ranged from Np3Ns to highly challenging Np6Ns. The methodology has also been implemented using medronic acid and imidodiphosphate to obtain NpnNs analogues, some of which are unprecedented.

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Physicochemical Aspects of Aqueous and Nonaqueous Approaches to the Preparation of Nucleosides, Nucleotides and Phosphate Ester Mimics

Cited by 8 publications

References 83 publications

Analysis of Nucleosides and Nucleotides in Plants: An Update on Sample Preparation and LC–MS Techniques

Analysis of Nucleosides and Nucleotides in Plants: An Update on Sample Preparation and LC–MS Techniques

Synthetic Strategies for Dinucleotides Synthesis

Ball‐Milling to Access Dinucleoside Polyphosphates and Analogues

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