The Chemical Biology of Phosphorus
Chapter 11: C–P Bonds in Biology: Phosphonates and Phosphinates
Published:29 Oct 2020
Special Collection: 2020 ebook collectionSeries: Chemical Biology
The Chemical Biology of Phosphorus, The Royal Society of Chemistry, 2020, ch. 11, pp. 331-354.
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While the great preponderance of phosphate metabolites contain –O–P–O32− bonds, there is a subset of ∼250 microbial and lower eukaryotic scaffolds with direct C–P bonds. Most have one C–P bond (–C–PO32−) and are classified as phosphonates. A much smaller number have two C–P bonds (–C–PO2−C–) and are phosphinates. There appears to be only one enzyme-catalyzed route for conversion of C–O–PO32− to C–PO32− frameworks. Phosphoenolpyruvate (PEP) is converted by PEP mutase to phosphonopyruvate as the entryway to all known naturally occurring phosphonates. Phosphonopyruvate is then operated on by suites of enzymes that diversify the scaffold to various antimetabolites.