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Related Concept Videos

The Phosphorus Cycle01:21

The Phosphorus Cycle

37.2K
Unlike carbon, water, and nitrogen, phosphorus is not present in the atmosphere as a gas. Instead, most phosphorus in the ecosystem exists as compounds, such as phosphate ions (PO43-), found in soil, water, sediment and rocks. Phosphorus is often a limiting nutrient (i.e., in short supply). Consequently, phosphorus is added to most agricultural fertilizers, which can cause environmental problems related to runoff in aquatic ecosystems.
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Ion Exchange01:17

Ion Exchange

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Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or...
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Phosphodiester Linkages01:01

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Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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EDTA: Chemistry and Properties01:22

EDTA: Chemistry and Properties

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Polydentate ligands are most widely used in complexometric titrations because they form more stable complexes with the metal ions than mono- or bidentate ligands due to the chelate effect. Examples of polydentate ligands are ethylenediaminetetraacetic acid (EDTA), crown ethers, and cryptands. The most important feature of optimal polydentate ligands is the ability to form 1:1 complexes in a single-step process. Amino carboxylic acid derivatives are frequently used as complexing agents. EDTA is...
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Dynamic Phosphorus: Thiolate Exchange Cascades with Higher Phosphorothioates.

Jules Bouffard1, Filipe Coelho1, Naomi Sakai1

  • 1Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.

Angewandte Chemie (International Ed. in English)
|October 17, 2023
PubMed
Summary

This study introduces phosphorus compounds as novel exchange centers for dynamic covalent chemistry. These non-toxic phosphorus compounds demonstrate efficient exchange reactions in various environments, including living cells.

Keywords:
Cascade ExchangeDynamic Covalent ChemistryMolecular WalkersPhosphorothioatesThiol-Mediated Uptake

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Area of Science:

  • Chemical Synthesis
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Dynamic covalent chemistry (DCvC) relies on reversible bond-forming reactions.
  • Pnictogens, like phosphorus, are underexplored as core components in DCvC systems.
  • Developing new DCvC platforms is crucial for advanced materials and biological applications.

Purpose of the Study:

  • To introduce phosphorus-based compounds as versatile exchange centers for DCvC.
  • To demonstrate the cascade exchange of phosphorotrithioates and phosphorotetrathioates with thiolates.
  • To investigate the factors influencing exchange rates and the behavior of these systems in biological contexts.

Main Methods:

  • Synthesis and characterization of neutral phosphorotri- and -tetrathioates.
  • Demonstration of cascade exchange reactions in organic solvents, aqueous micellar systems, and live cells.
  • Kinetic studies to determine the influence of pH, electrophilicity, and nucleophilicity on exchange rates.
  • Computational simulations of molecular walking along Hammett gradients.
  • Cytotoxicity assays using HeLa Kyoto cells.

Main Results:

  • Phosphorus compounds function effectively as exchange centers in DCvC.
  • Cascade exchange reactions were successfully achieved with thiolates under various conditions.
  • Exchange rates are pH-dependent and influenced by the electrophilicity of the phosphorus center and nucleophilicity of thiolates.
  • Phosphorotetrathioates exhibit higher exchange rates than phosphorotrithioates.
  • Dynamic phosphorus compounds are non-toxic and facilitate thiol-mediated cellular uptake.

Conclusions:

  • Neutral phosphorotri- and -tetrathioates represent a novel class of building blocks for dynamic covalent chemistry.
  • The demonstrated exchange reactions are efficient, tunable, and applicable in biologically relevant media.
  • These findings open new avenues for designing dynamic materials and developing targeted drug delivery systems.