Phosphonates: Their Natural Occurrence and Physiological Role

Abstract

The first natural compound containing carbon-to-phosphorus bond-ciliatine was discovered 60 years ago, and for four decades, phosphonates were considered simply as a biological curiosity. Finding the importance of these compounds in biogeochemical phosphorus cycling, their role in methane production, as well as discovery of numerous phosphonates and phosphonopeptides of promising antibacterial and antifungal activities has stimulated the development of studies on this class of compounds, especially on their metabolism and biochemistry. These studies are driven by the use of 31 P NMR and by a clever combination of genomics and innovative chemistry by using the method of selective labeling of metabolites. These studies revealed unusual and interesting chemistry of these compounds.

Biogeochemical and omic evidence for paradoxical methane production via multiple co-occurring mechanisms in aquatic ecosystems

“…Quantifying the relative contributions of allochthonous vs. autochthonous MPn production—as well as broader P acquisition dynamics—is therefore essential to understanding CH 4 production in freshwater. Phosphonate compounds were once thought to be resistant to breakdown and their formation remains poorly understood (17, 65). Under P limiting conditions, competition for these and other P compounds among multiple groups of organisms will be intense, and potentially variable in space and time.…”

Pseudoceratonic Acid and Moloka’iamine Derivatives from the Red Sea Verongiid Sponge Pseudoceratina arabica

“…Hydrazine derivatives and other dinitrogen-containing features are commonly found in natural compounds of terrestrial, microbial, and marine origin [23,24]. Similarly, derivatives of phosphoramidic acid are represented in different chemical entities of natural origin [25,26]. A literature search revealed only four compounds with N-N-linked-phosphorous moiety including fosfazinomycins A and B from Streptomyces lavendofoliae [27], FR-900137 from Streptomyces unzenensis [28,29] and O,O-dipropyl (E)-2-(1-methyl-2-oxopropylidene)phosphorohydrazidothioate (E)-oxime) from the dinoflagellate Gymnodinium breve [30].…”

Introductory Chapter: Phosphorus - Nature’s Versatile Pentavalent and Tetrahedral Covalent Building Block and Agent for Energy, Disease and Health

“…• The chapter by Kafarski (Wrocław University) involves a discussion of the biological use of phosphonates; these are phosphates groups in which there is one carbon attachment (see Figure 1) [38]. Biogeochemistry and phosphorus cycling is discussed.…”

“…Structures of fosmidomycin analogs are also shown and discussed. Phosphonates can help form methane [38].…”