Phosphonate and phosphinate metabolism

Natural products containing carbon-phosphorous bonds, so-called C-P compounds, are derivatives of phosphonate and phosphinate with substitution of alkyl group for hydrogen of phosphorus-hydrogen bonds. C-P compounds have been found in many organisms, but only protists and bacteria, mostly Actinobacteria, have biosynthetic capacity. A common reaction in the biosynthetic pathway is C-P bond forming reaction from phosphoenolpyruvate (PEP) to phosphonopyruvate (PnPy) catalyzed by PEP phosphomutase. 2-Aminoethylphosphonate (AEP) is the most abundant C-P compound in the natural world. AEP derivatives include phosphonoprotein, phosphonoglycan, and phosphonolipid. Other known C-P compounds are bioactive substances used in medicine (antibiotics) and agriculture (herbicide) such as fosfomycin, FR-33289, rhizocticin, and bialaphos.

Metabolism; Metabolism of other amino acids

PMID:19489722

Metcalf WW, van der Donk WA

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Annu Rev Biochem 78:65-94 (2009)

PMID:19053721

Xiao Y, Lee K, Liu P

Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway.

Org Lett 10:5521-4 (2008)

PMID:17168571

van der Donk WA

Rings, radicals, and regeneration: the early years of a bioorganic laboratory.

J Org Chem 71:9561-71 (2006)

PMID:15616300

Blodgett JA, Zhang JK, Metcalf WW

Molecular cloning, sequence analysis, and heterologous expression of the phosphinothricin tripeptide biosynthetic gene cluster from Streptomyces viridochromogenes DSM 40736.

Antimicrob Agents Chemother 49:230-40 (2005)

PMID:15574905

Schwartz D, Berger S, Heinzelmann E, Muschko K, Welzel K, Wohlleben W

Biosynthetic gene cluster of the herbicide phosphinothricin tripeptide from Streptomyces viridochromogenes Tu494.

Appl Environ Microbiol 70:7093-102 (2004)