Screening for carbon-bound phosphorus in marine animals by high-resolution 31P-NMR spectroscopy: coastal and hydrothermal vent invertebrates

Quin, Louis D.; Quin, G. S.

doi:10.1016/s1096-4959(00)00310-9

Cited by 28 publications

(28 citation statements)

References 15 publications

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“…), and can also be found as phosphate ions, polyphosphates, phosphate esters and phosphonates in cnidarians and other marine invertebrates (Kittredge and Roberts , Kittredge et al. , Quin and Quin , Godinot et al. ).…”

Section: Phosphorus‐containing Compounds In the Symbiotic Associationmentioning

confidence: 99%

“…, Steen ), accounting for between 10–50% of cellular particulate phosphorus. Although their metabolic importance remains unclear (Quin and Quin ), the presence of resistant C‐P bonds in phosphonates has been suggested to provide increased strength and protection to organisms that lack protective outer coatings of chitin or cellulose (Rosenberg ). Other phosphorus‐containing compounds have been identified in anthozoans and/or symbionts such as sugar monophosphates, and polyphosphates (ATP, ADP, adenylate, and reductants; Steen , Jackson , Rands et al.…”

Section: Phosphorus‐containing Compounds In the Symbiotic Associationmentioning

confidence: 99%

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Phosphorus metabolism of reef organisms with algal symbionts

Ferrier‐Pagés

Godinot

D’Angelo

et al. 2016

Ecological Monographs

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Phosphorus (P), an essential structural and functional component of all living organisms, is considered to be the ultimate limiting nutrient in marine ecosystems. To optimize its acquisition, marine species such as protozoa, sponges, foraminifera, clams, and reef corals, among others, have entered symbiotic relationships with algae, which recycle waste products of the animal host and transform dissolved inorganic nutrients into organic molecules, making them bioavailable to their host. Such associations provide a competitive edge in an environment where ambient nutrient availability is low. The aim of this review is to summarize the current knowledge on the P sources available to reef organisms with algal symbionts, to discuss the means by which P is taken up and stored within the symbiosis, and to assess the effects of eutrophication‐induced phosphate enrichment on the algal and host physiology. Finally, we give an overview of knowledge gaps and open questions that should be addressed to better understand the role of phosphorus in reef symbioses functioning.

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Section: Phosphorus‐containing Compounds In the Symbiotic Associationmentioning

confidence: 99%

Section: Phosphorus‐containing Compounds In the Symbiotic Associationmentioning

confidence: 99%

Phosphorus metabolism of reef organisms with algal symbionts

Ferrier‐Pagés

Godinot

D’Angelo

et al. 2016

Ecological Monographs

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“…2-AEP replaces its structural analog ethanolamine phosphate as a component of the phosphonoglycolipids common in the cell membrane of many invertebrates and is considered – along with its N -methylated derivatives – to be the most abundant and ubiquitous marine C–P compound (Hilderbrand, 1983; Hori et al, 1984; Quin and Quin, 2001). The mechanism of C–P bond cleavage by phosphonatase, a member of the halo acid dehalogenase superfamily, involves the formation of a Schiff base intermediate between a lysine residue at the active site of the enzyme and the phosphonoacetaldehyde carbonyl group; this activates the phosphonate group for attack by an active site nucleophile (Baker et al, 1998; Morais et al, 2004).…”

Section: Enzymes Of Phosphonate Catabolism In Microorganismsmentioning

confidence: 99%

The genes and enzymes of phosphonate metabolism by bacteria, and their distribution in the marine environment

2012

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Phosphonates are compounds that contain the chemically stable carbon–phosphorus (C–P) bond. They are widely distributed amongst more primitive life forms including many marine invertebrates and constitute a significant component of the dissolved organic phosphorus reservoir in the oceans. Virtually all biogenic C–P compounds are synthesized by a pathway in which the key step is the intramolecular rearrangement of phosphoenolpyruvate to phosphonopyruvate. However C–P bond cleavage by degradative microorganisms is catalyzed by a number of enzymes – C–P lyases, C–P hydrolases, and others of as-yet-uncharacterized mechanism. Expression of some of the pathways of phosphonate catabolism is controlled by ambient levels of inorganic P (Pi) but for others it is Pi-independent. In this report we review the enzymology of C–P bond metabolism in bacteria, and also present the results of an in silico investigation of the distribution of the genes that encode the pathways responsible, in both bacterial genomes and in marine metagenomic libraries, and their likely modes of regulation. Interrogation of currently available whole-genome bacterial sequences indicates that some 10% contain genes encoding putative pathways of phosphonate biosynthesis while ∼40% encode one or more pathways of phosphonate catabolism. Analysis of metagenomic data from the global ocean survey suggests that some 10 and 30%, respectively, of bacterial genomes across the sites sampled encode these pathways. Catabolic routes involving phosphonoacetate hydrolase, C–P lyase(s), and an uncharacterized 2-aminoethylphosphonate degradative sequence were predominant, and it is likely that both substrate-inducible and Pi-repressible mechanisms are involved in their regulation. The data we present indicate the likely importance of phosphonate-P in global biogeochemical P cycling, and by extension its role in marine productivity and in carbon and nitrogen dynamics in the oceans.

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“…NMR spectral characteristics of aminophosphonic acids and their derivatives are an important and common tool both for determination of structure peculiarities of aminophosphonic acids and identification of new and known compounds in reaction mixtures and biological samples [10]. For example, 31 P-NMR analysis has been successfully used to detect and discriminate aminophosphonic acids AEP 1 and MeNHCH 2 CH 2 P(O)(OH) 2 from other phosphoric acid derivatives in sea animals [11]. The solid-state 31 P-NMR cross-polarization magic angle spinning technique enables determination of the amount of CÀP forms in the total phosphorus in sea anemones [12].…”

Section: Physical/chemical Properties and Analysismentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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Screening for carbon-bound phosphorus in marine animals by high-resolution 31P-NMR spectroscopy: coastal and hydrothermal vent invertebrates

Cited by 28 publications

References 15 publications

Phosphorus metabolism of reef organisms with algal symbionts

Phosphorus metabolism of reef organisms with algal symbionts

The genes and enzymes of phosphonate metabolism by bacteria, and their distribution in the marine environment

Chemistry of Aminophosphonic Acids and Phosphonopeptides

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